Bareboat Charter Guide for Beginners: How to Take Your First Sailing Vacation

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma) on a bvi catamaran charter

Photo: spectacular evening in North Sound, BVI on our first bareboat yacht charter trip

Why go on a bareboat yacht charter trip?

To me, there is no better vacation than a bareboat charter on your own sailing yacht. It has everything I’m looking for – sailing, saltwater, unbelievable surroundings, a new adventure each day, deep sea fishing, good food, fun with friends/family, and epic sunsets.

It’s not for everyone, but if this appeals to you, once you try it you will never want to go back to your old vacation ways. As soon as we finish a bareboat charter trip, I’m already starting to think about the next one.

Forget those touristy excursions. Get away from the crowds and access amazing places other people can’t reach. Learn to sail, understand what it takes to go on yacht charter trip, and create your own memories and adventures to last a lifetime. If you haven’t been before, it’s not as hard as it may seem.

Look forward to other sailing destinations such as the British Virgin Islands, Exumas Bahamas, Spanish Virgin Islands, Dry Tortugas, Greece, and French Polynesia.

In this bareboat charter guide for beginners, I’m going to tell you everything you need to know to give you the confidence to start planning your first trip. Let’s get started, there is not a moment to lose!

Anchorage in Anegada at Setting Point
On our bareboat charter yacht in Anegada, BVI back in 2018

Four ways to go on a yacht charter trip

A bareboat charter isn’t the only way to go on a yacht sailing vacation.

Bareboat charter

This is what my article focuses on – you serve as the captain, supply the crew, make provisioning arrangements, and decide where you want to go. The charter company will qualify your sailing experience to make sure you have a safe and fun trip.

Crewed charter

This is a great option if you want to decide if these types of trips are for you. You choose a yacht that comes with a dedicated captain and chef/hostess.

It’s the “all-inclusive” option. They will cook gourmet meals for you, mix you drinks, and tailor a sailing itinerary to your preferences. The yachts usually come with a wide variety of water toys.

Keep in mind, as you might expect, this is the most expensive option.

Bali 5.4 helm station view
At the helm of a Bali 5.4 in the Exuma Bahamas

Captained charter

You book this type of trip with one of the charter companies, and they help to provide you with a skipper. Choose also to add on a chef.

While this sounds similar to a crewed charter, you don’t know exactly who will be assigned to your trip. The experience you have will be less predictable and the customer service is perhaps not quite as top notch.

By the cabin charter

This type of shared charter let’s you book one or two cabins. You’ll have strangers aboard that you share the charter trip with. It may be offered by the charter companies or by one of the many crewed options available.

What is a bareboat charter?

A bareboat charter simply means that you rent a boat from a charter company for a defined period of time. Most importantly, the arrangement does not come with a captain, crew, or provisions – it is up to you to provide those things.

On your charter, you have the freedom to do whatever you’d like (within reason or course) during your trip – sailing, snorkeling, fishing, etc. These are more of my favorite boat trip activities.

Fowl Cay in the Exumas
Lunch snorkel spot in the Exumas on our 2021 yacht charter trip

Skills that you need for a bareboat charter

You do not need to be sailing certified to charter a sailboat. If you have substantial sailing experience on similarly sized yachts, you can provide a sailing resume to qualify with the various charter companies.

We’d recommend going to sailing school and getting certified anyway. We took three courses through the American Sailing Association:

ASA 101: Basic Keelboat Sailing – This is the introductory course for sailing. We had no sailing experience and wanted to learn when we were living in San Diego.  We also joined a local sailing club to practice our skills once or twice a month in San Diego Bay. The course is two days and usually completed over a weekend.

ASA 103: Basic Coastal Cruising – Builds on the basics you learned in 101 and further develops your seamanship.

ASA 104: Bareboat Cruising – Teaches you more about a boat’s systems and other skills such as anchoring, docking, provisioning, and advanced sail trim.

It’s worth nothing that ASA 103 and 104 are often offered as a combo course. We suggest taking 101, getting some practice in, and then if you decide sailing is for you, go take the 103/104 combo course. The 103/104 combo can also be done over a weekend.

If you have some sailing experience and just want the resource, you can purchase ASA’s book for the bareboat course.

The SmarterCharter book is also a great practical guide for skills specific to bareboating. There is also a monohull version.

Catamaran downwind sailing on a bareboat charter trip
Easy downwind sailing in 10 knots

Sailing

Do you need to know how to sail? No! You can always hire a skipper or take a crewed charter for your first time if you want to test the waters first with this type of trip. The skipper can take you places that you might not have the confidence to go as a beginner.

Another option is to charter a motor yacht. Marine Max specializes in power catamarans.

You do not need to sail the whole time. One trip we had very light winds on several days, so we just motored. You will have plenty of fuel, even if you motor the majority of the time. You shouldn’t need to worry about stopping at a marina to refuel.

Anchoring and mooring

Do you need to know how to anchor? Yes! This is a skill that you should be comfortable with. Even if you only plan to tie off to mooring balls, consider a situation where all of the mooring balls are taken. In this case you may be forced to anchor.

We’d recommend picking a first destination such as the BVI where you can pick up a mooring ball at most popular anchorages. Familiarize yourself with how to reserve Boaty Ball moorings in the BVI, if necessary. This will keep the stress down for your first trip – you shouldn’t need to anchor overnight. Practice anchoring at a day lunch stop, such as Sandy Spit near Little Jost Van Dyke in the BVI.

On our first trip we did just this – we used mooring balls. Now that we have plenty of experience, we seek out secluded anchorages and enjoy anchoring overnight.

This video from Sailing La Vagabonde provides a good overview about how mooring balls work.

Dodging squalls on the way to the Dry Tortugas on a bareboat charter trip
Getting ready to deal with an isolated squall in the Florida Keys

Weather 

For a complete guide to BVI weather and marine forecasting, check out my post here.

Plan to take your first trip during periods when settled weather can be expected. For the Bahamas and the Caribbean this means April-May and late November. Tropical systems are unlikely. The trade winds blow consistently out of the east at 10-15 knots – perfect conditions to practice your seamanship.

Plan to monitor weather conditions for the week leading up to your trip. This will help you to notice patterns that could affect your trip. Marine weather forecasts are available online from resources such as the National Weather Service. Your charter company will provide more detail on how to monitor weather during your charter.

If sailing in the Virgin Islands, know if a ground swell is forecasted. They are common between November and April. Make sure you are check the forecast since it could have an impact on your itinerary. Any anchorage exposed to the north will be unusable if a ground swell is running. The NWS Marine Forecast will include information about ground swells. They are very well forecasted.

You should also be familiar with how local conditions such as tides and island geography can affect your boat – such as being backwinded (this is more important if you plan to anchor).

Systems

ASA 104 should prepare you well to manage the boats systems. The most important part is making sure you are monitoring fuel, water, and battery levels. Ask lots of questions during your boat briefing and make sure you are comfortable working the electrical system by yourself. For example, they will explain how to charge the batteries and turn on the AC system.

Navigation

You’ll want to understand how to read the water color, read charts, and plan a route. Pick a destination like BVI that has easy point and shoot navigation.

Docking

Docking can be stressful and intimidating. You can read all about it, but unfortunately the only way you get better is by practicing.

Here’s the solution – for your first trip, request assistance from the charter company when leaving the marina. They can help with the dock lines and also pilot the boat out for you. Use them! It will keep the stress down. At the end of the trip, reach them on the radio and they will send someone out in a dinghy to pilot the sailboat back in.

Practice docking on your own terms under ideal conditions.

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Our first bareboat charter trip in virgin gorda sound
Aboard a 33 foot monohull in North Sound, BVI - the trip that started it all for the Yacht Warriors

What to consider when choosing a yacht charter boat

On our first boat trip, the one that started it all, we went out on a 37 foot, 2 cabin monohull. Every trip we’ve taken since has been on a ~45 foot 4 cabin, 4 head catamaran.

But, pick what you like! There is no right answer here. A couple things to consider:

Catamaran vs. Monohull

This can be a fiercely debated topic amongst seasoned sailors. For a sailing vacation, I believe a catamaran is the way to go. I write about it in more detail here. And if you want a complete review of a catamaran with lots of pictures, check out my thoughts on the Bali 5.4.

We enjoy having more space, a salon above the waterline, and the stability two hulls provide. I also find that I can maneuver a catamaran more easily because it has twin engines.

We also tend to go vacation with a crew of 8, and this works well with the space cats provide.

As far as sailing performance goes, monohulls tend to sail closer to the wind and can be faster than the catamarans that you’ll find in bareboat fleets. They will also keel over, which some people enjoy.

Age

After you’ve picked a type of boat, I recommend that you choose the newest one that you can afford. Older yachts tend to have a greater chance of a breakdown. Your charter company will do their best to fix any issue, but it can definitely disrupt your plans (speaking from experience here!).

Spending a bit more on a newer sailboat is a good insurance policy.

Brand

Sometimes it will just come down to what’s available. Don’t sweat it. We’ve sailed on Lagoons, Leopards, and Balis. You’ll have a great time on any of them.

One feature we love is a fly bridge – essentially a common area up top that includes the helm station where everyone can hang out while cruising. We find that this is more fun than a separate area where the skipper operates the boat.

Bali 5.4 in the Exumas on a bareboat charter trip
Plenty of room for the whole crew on this Bali catamaran

Charter Company

We’ve used many different charter companies over the years. In the British Virgin Islands, you have many to choose from. In other sailing destinations, you may only have one or two options.

Each of them has different bases or marinas they operate from – some will have specific amenities that might appeal to you.

Reputation for quickly addressing any maintenance issues should also factor into your decision.

This is a complete list of the bareboat charter companies that we have relationships with, including destinations they operate.

painkillers at the soggy dollar bar in white bay jost van dyke
Lady crew members lined up with painkillers at the Soggy Dollar Bar in BVI

Picking your crew

Picking your crew members may be the most important decision of your entire trip. Who you decide to take with you matters. We have lots of friends, but we wouldn’t want to spend 8 days on a boat with all of them (no offense friends!).

Choose wisely. Will they get along? Are they flexible if plans change? Would they be OK skipping a shower if the water runs low? Are they willing to help out (with cooking, cleaning, etc)?

palm-tree-banner
Planning a British Virgin Islands trip? Start here.

How long should I plan the yacht charter trip for? 

We like to do trips that include 8 nights on the boat. The first night is usually a later check in and spent overnight in the marina after a day of travel. That makes for 7 full days of exploring and adventure on your sailing charter.

You can also consider staying in a hotel for your first night, but we like to stow away provisions and get familiar with the boat. It also allows for an earlier departure on your first full day – don’t waste valuable cruising time in the marina! 

Provisioning

Most charter companies can provide a provisioning service. Coordinate with your crew for meal planning and make your selections. The food and beverages will be aboard your sailboat when you arrive, what joy!

Check out our post on how to get the crew organized to help with provisioning planning.

You can also do the shopping yourself depending on the destination – Key West and the Spanish Virgin Islands are good candidates.

For a first time bareboat charter, keep it easy and let one of the provisioning services handle it for you.

We always plan for big breakfasts – eggs, bacon, and hash browns. Start your day right!

Lunches we keep simple since we are usually on the move or exploring ashore – sandwiches and chips work great.

For dinners, consider how many meals you’ll plan to eat ashore at beach restaurants. The other nights, simple is always better. Pasta, burgers, and tacos are some of our staples. Spend less time in the galley and more time soaking up that Caribbean sunset.

We also recently started preparing meals ahead of time, freezing them, and taking them with us. Read about my other top 10 bareboat charter travel hacks to help you have more fun and lessen the stress.

Palm Cay Marina in Nassau, gateway to an Exuma Yacht Charter
One of the marina bases that you might visit - this at Palm Cay, the gateway to the Exumas

What is the check-in and check-out process like? 

Check-in

You will typically board your boat in the evening. Get comfortable, and in the morning, a representative from the charter company will meet you for the boat briefing. Here’s what they’ll cover – I talk more about what to expect for the boat briefing on this post. If you sign up for my free newsletter, I’ll send you a pdf version of my Boat Briefing Checklist that you can print and take with you on your first trip.

  • Cruising grounds – they can give you advice on where to go and what areas may be off limits. 
  • Boat systems and operation – you’ll do an inventory and cover all you need to know about the sailboat’s systems and sailing equipment. Have a list of questions prepared in case they miss something.
  • Safety – such as where the life jackets, life raft, plugs, and emergency tiller are located. You should also cover radio procedures if you need a refresher.
  • Communications – how to get in touch with the charter company if you have a repair issue or what to do when you are ready to return to the marina.

Check-out

Check out is usually mid morning on your last day. You can either return to the marina the night before, or stay in an anchorage nearby.

Sometimes they ask you to visit the fuel dock, but you can also pay the charter company to handle this service for you. They might do another inventory with you, but usually you just need to disclose if anything is broken or missing.

Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage
Spanish Virgin Islands' sunset on the west coast of Culebra

What does a bareboat charter cost?

Expect to pay anywhere from $5,000 to $20,000 for most bareboat charter trips. So what inflluences the pricing?

  • Type of yacht: monohulls are going to be more affordable than catamarans (all else equal)

  • Size of yacht: not surprisingly, the longer and bigger the boat, the more expensive it will be

  • Number of cabins: a 3-cabin catamaran with an owner’s cabin is going to be more affordable than a 4-cabin equivalent

  • Age: you’ll pay a premium for newer boats (but also might experience fewer maintenance issues)

  • Season: when you charter matters a lot. The high season holiday periods are always the most expensive, whereas, you can find great deals (and solitude) in the low season when tropical disturbances might threaten in the Caribbean

  • Discounts: charter companies offer various promotions, but you can usually expect to receive an early booking or a repeat charter discount (5 or 10% each). Last-minute discounts are another great way to save money if you are flexible (or work from home!)

Read more about bareboat charter pricing, the components of your quote, and what things you will need to budget for separately.

The Indians, BVI
Popular snorkel spot: The Indians in the BVIs

Charter destination for your first trip: British Virgin Islands

There is no better sailing trip for beginners than the British Virgin Islands. Here’s why:

  • Idyllic Caribbean surroundings – numerous tropical islands that rise sharply out of the ocean. Plenty of protected anchorages. Coconut palm lined white sandy beaches. Great snorkeling and fishing. What else do you need?
  • Settled weather – you can expect steady trade winds out of the east year round. If you avoid the summer months when tropical systems can develop, there is little risk of a major weather disruption.
  • Easy navigation – there are few navigational hazards and you can usually see the islands you are navigating towards.
  • Mooring balls – there are plenty of well maintained balls available, making it easier for beginners.
  • Well established bareboat yacht charter industry – lots of operators, a deep bareboat charter fleet, plenty of restauraunts that serve boaters, and many services to help make your trip easy.

If you have a cruising ground close to home that offers some of these same features, that could be a great option too!

Request a BVI Yacht Charter Quote

We have relationships with all of the BVI yacht charter companies and have personally chartered with many of them.
Let us find you the best option - it doesn't cost you anything extra.
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North Sound in Virgin Gorda, BVI

First time BVI bareboat charter sailing itinerary

We’ve visited the BVIs four times now, and every time our itinerary gets a little bit better. Here’s what I would do on a first time visit. (update – here’s a more in depth post about a first time BVI sailing itinerary).

You can also visit this link to see my other articles I’ve written about the British Virgin Islands. The FAQ section also address many common questions.

My sailing plan also assumes you take the sleep aboard option on your first day.

Travel day
Day 1: Travel day
Arrive, get settled in, and stow away your provisions. Familiarize yourself with the boat's systems if you'd like. Crack a beer - you've made it!
Travel day
Cooper Island Beach Club
Day 2: Cooper Island
Plan for an easy, short sail on your first full day on the water. Cooper Island Beach Club is a perfect stop. Grab a mooring ball and head ashore to enjoy the facilities, bar, and restaurant. Arrive early - the mooring balls fill up quickly! You may also enjoy a snorkel at Cistern Point to the south.
Cooper Island Beach Club
Devil's Bay at the Baths, a top BVI Beach
The Baths & North Sound
Day 3: Baths & North Sound
Get an early start and sail up the Sir Francis Drake Channel. Stop for lunch at The Baths, a must see visit. Swim ashore and hike through the monstrous boulders to Devil's Bay.

Round Virgin Gorda and enter North Sound through the well-marked channel. There are many places to choose from including the Bitter End Yacht Club, Saba Rock, and Leverick Bay. Plenty of mooring balls are available.
Devil's Bay at the Baths, a top BVI Beach
The Baths & North Sound
Sunset at Setting Point in Anegada on a BVI yacht charter
Anegada & Setting Point
Day 4: Anegada
Some will say to avoid Anegada if you are a beginner, but I disagree. The channel is well marked and it is only a couple hours sail offshore. Check with your charter company. Anegada is a low lying, coral island making up part of Horseshoe Reef - the 4th largest barrier reef in the world. Rent a car and visit the spectacular beaches on the north shore. Enjoy a freshly caught spiny lobster dinner at one of the many Setting Point restaurants.
Read more about Anegada
Sunset at Setting Point in Anegada on a BVI yacht charter
Anegada & Setting Point
sunset at Cane Garden Bay in the BVIs on a bvi catamaran charter
Cane Garden Bay
Day 5: Cane Garden Bay
Head back south and sail counter clockwise around Tortola. Monkey Point at Guana Island is a great snorkel lunch stop. Cane Garden Bay is a picturesque spot with lots of room and plenty of mooring balls. This is a great opportunity to head ashore and shop for additional provisions if you need them. There are lots of restaurants to choose from if you want to eat ashore.
sunset at Cane Garden Bay in the BVIs on a bvi catamaran charter
Cane Garden Bay
Sandy Spit BVI, a top 10 BVI beach
Sandy Spit
Day 6: Sandy Spit & Great Harbour
Make your way north and try your hand at anchoring near Sandy Spit. This is a fun day spot. Dinghy ashore for a picnic. Great Harbour at Jost Van Dyke is home to the famous Foxy's Bar. Enjoy some late night live music and dancing. Over the weekend, they have a famous Beach BBQ.
Sandy Spit BVI, a top 10 BVI beach
Sandy Spit
swimming at white bay jost van dyke
White Bay & the Soggy Dollar Bar
Day 7: White Bay & The Soggy Dollar Bar
Get an early start to grab a mooring ball on the east side of the bay. Check with your charter company to make sure it is not off limits. Enjoy a full day of beach bar relaxing and fun. The Soggy Dollar Bar is world famous for its invention - the Pain Killer. If you're a beginner, I don't recommend anchoring at White Bay. Stay at Great Harbour and dinghy over, or walk.
Read more about White Bay
swimming at white bay jost van dyke
White Bay & the Soggy Dollar Bar
The Indians, BVI
The Indians & the Bight
Day 8: The Indians & the Bight
Pass nearby St. John, USVI and head for a lunch stop and snorkel at The Indians. Make a loop around the rock formations and enjoy the abundant sea life. Stay overnight at the Bight and join the party at Willy-Ts, the famous floating pirate ship bar and restaurant. The Pirate's Bight restaurant is also a very good choice for a last night send off.
Read more about Norman Island
The Indians, BVI
The Indians & the Bight
Travel Home
Day 9: Travel Home
Leave early enough to motor back to the base to comply with checkout procedures. Radio your charter company on your way back in if you'd like help docking the boat.
Travel Home

Thanks for reading my bareboat charter guide for beginners.! If you enjoyed it, please subscribe or check out some of my other articles, like this one about my secret anchorages in the BVIs.

Sailing in Puerto Rico: Spanish Virgin Islands Cruising Guide

Sunset at Green Beach Vieques

The Spanish Virgin Islands may be my new favorite Caribbean bareboat charter destination. Solitude, beautiful beaches, and excellent fishing are just some of the highlights that rank at the top of my list of must haves for a boat trip. Many people describe the SVIs as what the British Virgin Islands were 20+ years ago: raw, quiet, undiscovered – I was too young back then, but I’ll take their word for it!

Located just to the west of the USVI and BVI, the islands of Vieques, Culebra, and Culebrita dominate the Spanish Virgin Islands cruising grounds. You’ll find all sorts of habitats including mangroves, rocky coastlines, vibrant coral, and gorgeous caribbean sandy beaches.

Top highlights include hiking to the lighthouse on Culebrita, catching lots of fish, visiting the notorious target practice tanks on stunning Flamenco Beach (or Playa Flamenco) at Culebra, and witnessing the bioluminescence at Mosquito Bay.

There are several wildlife refuges which help protect and make the Spanish Virgin Islands such a special place. This includes the Vieques National Wildlife Refuge which used to be controlled by the U.S. Navy until 2003.  You can still find several anchorages marked as off-limits to anchoring due to potential unexploded ordnance.

Don’t expect beach bars at every anchorage. This is a place to get away from it all and soak in the natural surroundings. I’m really looking forward to sharing our experience with you and hope this cruising guide inspires you to visit this overlooked and beautiful cruising ground. Here is what I’ll cover:

SVI Logistics and Planning

Source: Puerto del Rey

Travel from the U.S. is easy with several direct flights to Puerto Rico from the mainland, and there is no passport requirement for U.S. passport holders. However, there is only one yacht charter operator in Puerto Rico at Puerto del Rey.

Puerto del Rey is located in Fajardo, the boating hub on the Puerto Rican east coast. As you would expect, it has plenty of amenities which includes a small store for forgotten provisioning items. They also have golf carts that meet you upon arrival to take you and your gear down to your yacht.

Having charted in the Spanish Virgin Islands from Puerto Rico and the US Virgin Islands, I would actually recommend the later. The charter fleet is much deeper in the USVI and it is easy to clear in using the CBP ROAM app. I did this on my recent November USVI and SVI trip.

Make sure you are aware of the latest clearance requirements when entering and exiting. I talk more about how you can do this in my St. Croix and Culebra sailing itinerary.

Bareboat Charter Provisioning

Unloading at Puerto del Rey
Unloading upon arrival to Puerto del Rey

One thing that I love about this destination is that there is a Costco located in San Juan. We arranged with our charter company in advance for our driver to make this stop on our way to Marina del Rey.

This means cheaper prices and much more variety than what is typically available on a provisioning list. It is absolutely not as convenient (we arrived to the base after dark), but I think the payoff is worthwhile.  Worth noting that the Costco also carried beer, wine, and liquor.

Your charter will be able to provide you with a provisioning service so that you make your selections in advance and upon arrival, your groceries are already onboard. You may also have your driver stop at a grocery store along the way.

If chartering from the USVIs, provisioning services and grocery stores are plentiful.

Additional Cruising Guide Resources

Given that the Spanish Virgin Islands are less visited than their sister islands to the east, there are not as many cruising guides available.  Stephen Pavlidis’ book Cruising Guide to Puerto Rico is your best bet. Be aware that the last revision was done in 2015, so some information could be out of date. It is still an excellent resource.

Cruising Guide to Puerto Rico (Amazon)

Stephen Pavlidis' guide has some great, detailed information on what to do and where to go. The last update was from 2015, so some information could be outdated, especially navigation info.

I also like to use the Navionics Boating App for planning. You can research routes, anchorages, and fishing spots. The ActiveCaptain Community feature is also very helpful to learn from other sailors experiences.

Here’s the link to the chart that was aboard our catamaran. If you are chartering from the USVIs, you may be required to provide your own. It might be cheaper to print these out, which are freely available online.

  • NOAA 25650 – Virgin Passage and Sonda de Vieques, Scale 1:100,000 (Passage planning
    from western St Thomas to Culebra, Vieques and eastern Puerto Rico)
  • NOAA 25653 – Isla de Culebra and Approaches, Scale 1:20,000 (Large scale coverage of
    Culebra)
  • NOAA 25664 – Pasaje de Vieques and Radas Roosevelt, Scale 1:25,000 (Large scale coverage of western Vieques). No large-scale NOAA chart is available for all of Vieques
NV Atlas 11.1 Chart (Amazon)

Current edition of the SVI navigational chart that we found on our sailing yacht during our last trip.

When to go Sailing in Puerto Rico

An occasional squall is common, but they often don't last long

My favorite time of year to visit the Virgin Islands is April-May. The trades blow consistently out of the east at 10-20 knots. The weather is more settled and since this is considered the shoulder season, prices are cheaper.

Late November is also a great option, but the days are shorter and you run more of a risk of tropical mischief.

While the USVI and BVI can get very busy during peak season (Dec-Mar), I would not expect the SVIs to become quite as crowded. It sill flies under the radar as a destination and the bareboat fleet that serves the cruising grounds is much smaller.

For a more comprehensive overview of weather conditions, check out The Cruising Guide to the Virgin Islands. SVI is not covered, but the weather and cruising conditions information is applicable. You can also read my post about BVI marine forecasting and resources, which is just as applicable for the Spanish Virgin Islands.

Cruising Guide to the Virgin Islands (Amazon)

This guide DOES NOT cover the Spanish Virgin Islands, but it has some info on weather and cruising conditions that would apply.

Northerly Ground Swells

Ground swells are common between November and April. Make sure you check the forecast since it could have an impact on your itinerary. Any anchorage exposed to the north, such as Playa Tortuga at Culebrita, will be untenable if a ground swell is running.

The NWS Marine Forecast will include information about ground swells. They are very well forecasted.

Spanish Virgin Islands Sailing Itinerary

Our suggested bareboat yacht charter itinerary assumes 7 days on the water beginning in Puerto del Rey. I take you clockwise beginning with Culebra and then continuing on south to Vieques.

Why does this plan work?

The prevailing trade winds in the Spanish Virgin Islands are typically from the east. A current also runs from the east.

Sailing clockwise will afford you some protection from the lee of Culebra as you head east. Once you get down to Vieques, in normal conditions you’ll be sailing west, downwind under more comfortable conditions.

Spanish Virgin Islands sailing itinerary including Vieques and Culebra
Sample itinerary, heading clockwise around the Spanish Virgin Islands

Day 1: Overnight in Marina

We recommend coordinating with your charter company for an airport transfer from the airport to Puerto del Rey. They will be able to help schedule the pickup and make sure the vehicle is large enough for your crew and gear (and potentially provisioning items if you decide to stop on the way).

Get settled into your yacht, stow away your provisions, and familiarize yourself with the boat’s systems if you’d like. Crack a beer – you’ve arrived in paradise.

First night is spent overnight in the marina.

Day 2: Begin your trip on the west coast of Culebra

Culebra sunset at Carlos Rosario beach
Enjoying an epic first night's sunset at Carlos Rosario

Try and set your yacht up to be first in line for the boat briefing and walk through. You don’t want to waste valuable cruising time in the marina!

Get that sailing playlist jamming and head east towards Culebra – it is probably easiest to motor under the prevailing conditions: dead into the wind. Get those fishing lines in the water – there is not a moment to lose!

I love the Carlos Rosario mooring field – I’ve stayed multiple times. Take a dip and enjoy some of the best snorkeling of the trip at Carlos Rosarion. It can be accessed right from your mooring.

Relax, pour yourself a sundowner, and enjoy the sunset show off to the west.

Carlos Rosarion reef at Culebra Spanish Virgin Islands
A view to the north of the reef at Carlos Rosario

Day 3: Hike to World Famous Playa Flamenco

Hiking back from Flamenco Beach
Hiking to Playa Flamenco

We are staying put today, unless you’d prefer to explore Cayo Luis Pena. We’d suggest, however, going ashore for a hike to the world famous Flamenco Beach (Playa Flamenco). The trail is easily visible on satellite. Again, bring some shoes you don’t mind getting dirty. The hike is just under a mile and should take you about 30 minutes. The trail dead ends into the back beach parking lot.

Another option is to actually anchor in settled conditions at Playa Flamenco. We did this on our recent November trip when we were sheltering from strong southerly winds.

Tank at Flamenco Beach
One of the tanks previously used as target practice at Playa Flamenco

While I haven’t been to the South Pacific, Flamenco Beach feels distinctly like a beach that could be located in Tahiti or the other Channel Islands. It also holds the title of one of the top 10 beaches in the world. Aside from the beautiful setting, the main attraction is the abandoned tanks scattered across the beach that the US Navy used for target practice up until the 1970s. 

Make a day of it and relax. Food, restrooms, and beach chair rentals are available.

Once back on your yacht, enjoy another great sunset. If the weather is settled and you aren’t worried about losing your mooring ball to another boat, I highly recommend an evening cruise. Make a loop around the Cayos to the west and enjoy the rugged natural beauty of the area.

You can also consider switching mooring balls to Punta Tamarindo, just around the point to the south.

Our catamaran at anchor at Playa Flamenco
Our catamaran at anchor in front of the NE corner of Playa Flamenco as we got ready to ride out a storm

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Day 4: Picture perfect Culebrita

View of Culebrita, one of the Culebra anchorages
Beautiful view of Playa Tortuga and the lighthouse at Culebrita

The islands of Culebra have a distinctly different feel than Vieques. Rather than one large island, there are many hidden gems to explore. Another must see place is Culebrita and Playa Tortuga (Turtle Beach).

Make your way lazily around the northern shore of Culebra past Cayo Norte to Culebrita.

This was our favorite beach in all of the Spanish Virgin Islands. Crescent moon shaped, white sand, coconut palm lined, and few other visitors – what else could you ask for?

Make sure you are aware of any northerly ground swell forecast as this anchorage is exposed. If it is day stop only conditions, try the Bahia de Almodovar (Les Pelas) anchorage for your overnight.

Culebrita is a small, uninhabited cay with an abandoned lighthouse at its highest point. The only residents are wild goats that you will be sure to bump into. Grab a pair of hiking shoes you don’t mind getting dirty (mud, puddles, and goat droppings are expected), plenty of water, and head ashore.

Culebrita Hiking Map
Culebrita hiking map | Source: Google Earth

The hike to the lighthouse is about 3/4 of a mile and should take you about 20-30 minutes. You’ll be rewarded with a beautiful 360 degree panorama of the surrounding islands – the best view from any hike I’ve taken in the caribbean.

The old Spanish lighthouse dates back to 1886 and is interesting to explore. It is falling apart after battling it out with several hurricanes and it is not being maintained – use caution. You are not supposed to venture inside.

Relax and watch for turtles as you lime away the afternoon.

Day 5: Sail south to Vieques

Fishing route in Vieques
Great day fishing rounding the south coast of Vieques, pins mark where we landed fish | Source: Navionics

Get an early start for a longer day on the water as you make the passage from Culebra to Vieques. Again, get those fishing lines in the water. We did really well hooking up in 50-100 feet of water (see pins in the picture above). Mahi and mackerel were the catches of the day. If conditions warrant, head farther south to the drop.

Troll back and forth across this area to target the pelagic species: mahi-mahi (dolphin fish), tuna, and wahoo.  This may be a bumpy ride given the strength of the tradewinds.

If you want to step up your fishing game, check out our sailboat fishing guide.

Before you leave Culebra, you can also consider a provisioning stop in Dewey before you depart.

The protected bay in Culebra is also known as Ensenada Honda (which means deep cove). Colmado Milka is well stocked with food, liquor and ice. Anchor close to the Cayo Pirata in about 15 feet. Take your dingy under the Lifting Bridge where there are several other spots to tie off to.

Mahi hook up in the Virgin Islands
Mahi hook up off the drop south of Vieques
Town of Dewey at Culebra
Dewey, the main town of Culebra

If you prefer to stick around Culebra for another day, Ensenada Dakity is a lovely mooring field with great protection tucked in behind the reef at the channel entrance. You’ll enjoy minimal roll and a nice breeze over the reef. The sunrises here are spectacular.

Not to be confused with the Culebra Ensenada Honda, check out Ensenada Honda, the Vieques version, for your first overnight on this island.

Anchorage Details: Entering the Ensenada Honda anchorage can be tricky, but the charts are well marked – stick to the course shown on the charts. The water is not crystal clear so you’ll need to rely on your instruments and use extra caution. Depths range from 10-30 feet. We recommend tucking yourself farther in to the east side of the bay where it is shallower.

Ensenada Honda is extremely well protected. You will likely be the only boat here. Come here for the peace and quiet. There is no beach access given the mangroves that line the bay. For something different, launch the dingy and explore the mangrove river located in the far eastern edge. Expect to see some rays and a nurse shark or two if you are lucky.

Day 6: Isla Chiva lunch stop and the Bioluminescence of Mosquito Bay

Anchoring at Isla Chiva in Vieques
Getting ready to dive on the anchor at Isla Chiva

Get underway and head west around the coast of Vieques. Make for a lunch stop at Isla Chiva.

There are two anchorages, one on either side of the island. We recommend anchoring on the west side of Isla Chiva in 10-15 ft with a grassy bottom. There are a few patches of sand you can aim for when you drop the hook.

The beaches here are beautiful and you can often see the wild horses that come down to the shores edge. Dingy ashore for a picnic or enjoy the view from your catamaran (monohull is OK too!). 

Make sure you save some time for a snorkel over to Isla Chiva located at the dive spot marked on the charts. The last time we were here there were some large abandoned fish traps that were interesting to explore. If a SE swell is running or the trades are really blowing, snorkeling in this spot is not recommended.

After lunch, sail to Sun Bay Vieques. This a postcard worthy crescent moon shaped bay with a sandy beach and lined with coconut palms. It is just to the east of the town of Esperanza and within walking distance.

Anchorage Details: The best place to anchor is tucked up in the northeast corner to avoid as much swell as possible that wraps around into the bay. Holding is good in 10-20 feet with a grassy bottom. Make sure you get that anchor set. If the wind is really blowing, Puerto Ferro farther down the coast offers complete protection from all directions.

If you want to go ashore, you can beach your dingy on either side of the the swim buoys. Look out for the wild horses that may come up to say hi at the beach. Esperanza has a few options for dining and shopping. Use the cell phone service to check hours of operation since they may differ from what you’d expect.

Sun Bay can also be used as a base to tour Mosquito Bay, which has the claim to the brightest bioluminescence bay in the world. You’ll need to arrange a kayak tour as dinghies are not allowed. There are plenty of tour operators that can be found online and they will pick you up right at the Sun Bay Beach.

Day 7: Magical Green Beach

Sunset at Green Beach Vieques
Epic sunsets await at Green Beach

On the west coast of Vieques, Green Beach awaits.

Aside from the solitude, you come to Green Beach for the sunsets – they are epic with the main island of Puerto Rico and the El Yunque rain forest in the backdrop. Arrive early enough to also jump in the water for some snorkeling. You can expect to swim with sea turtles, rays, and lots of colorful fish. There are no amenities ashore, so plan to cook aboard.

Anchorage Details: the Green Beach anchorage is large and you’ll notice several markers on the chart. The water is usually crystal clear so pick a spot in 10-15 feet of water with a white sandy bottom. There will be areas of sea grass and coral/rock you should avoid. You are likely to have the place to yourself, but if you are there over the weekend, expect a few local boats that will join you.

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Want to learn more about Spanish Virgin Islands yacht charter? Start here.

Day 8: Final night at Isla Palominos, or return to the marina

Approaching Isla Palominos to anchor
On approach to pickup a mooring ball at Isla Palominos

Last day on the water!

If you have extra time you could head towards Cayo Santiago further down the coast of Puerto Rico. It’s known as monkey island. You can’t go ashore, but there is an anchorage on the west side. Drop the hook and dingy in closer to get a view of the monkeys which have been free roaming since 1938. There are approximately 1,000 rhesus macaques monkeys that call the island home.

Isla Palominos is a great last night anchorage. It’s close enough to motor back the next morning before you debark and head home. 

It’s a very popular local destination, so don’t expect any peace and quiet! You have been warned.

Upon returning to the marina, your charter company may request that you first stop at the fuel dock – leave yourself plenty of time to checkout and return to the airport the next morning.

I hope you enjoyed my post about the Spanish Virgin Islands and sailing in Puerto Rico. If you are new to sailing trips and enjoyed this post, subscribe to my newsletter check out our beginner’s guide here.

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Sailboat Fishing Guide: How to Fish from a Sailboat

Mutton snapper caught while trolling in the Virgin Islands

Sailboat fishing is one of my favorite activities during our boat trips. Fortunately, many of the most popular sailing destinations like the Bahamas and British Virgin Islands (check out my BVI specific fishing tips or Exuma fishing guide) are also excellent places to fish.

Even if you aren’t an experienced angler, with a little planning you can have a lot of success. Here’s what you need to know to catch some serious fish and turn your yacht into a fishing sailboat.

Table of contents:

Fishing tackle and equipment

Northern Exumas Wahoo
Wahoo we caught with a diving lure in the Exumas

To rent, or to bring your own?

On our first few trips, we rented fishing equipment, but now we bring our own quality gear. A few things to consider…

Renting

Most charter companies should have an option to rent a rod, reel, and small tackle box for around $20/day. They will also provide a rod holder and gaff. Check in advance if they offer this option and what is included. You should expect to bring your own lures and additional fishing tackle.

Ye be warned: don’t expect quality gear – we’ve had a lot of problems the few times that we’ve rented. The equipment gets a lot of use and tends to be poorly maintained.

Renting is the cheaper option if you aren’t serious about fishing. Buying your own equipment is an investment that will take a couple trips to payback.

For smaller reef fish, the rented equipment should be just fine! If you want to go after the bigger pelagic deepwater fish, consider bringing your own setup.

Bring your own gear

The biggest factor to consider with bringing your gear on these fishing trips is the added headache of dealing with the airlines. You’ll need to check your rods and potentially pay an extra fee. United, for example sometimes tries to charge $200 if the container is over a certain length. If you have preferred status with an airline, you might be immune.

You should also plan to check fishing tackle and filet knives.

Rods

I have two, 6 foot jigging rods that I bring. If you have a local fishing store (mine is Fishing Tackle Unlimited), ask them what they’d recommend – there are lots of options. You can get away with shorter rods for trolling – it might help save you money on airline fees.

I like the jigging rod since you can use it for lower speed trolling, jigging, and bottom fishing. If you bring spinning reels, you can also use them for casting.

I use this Plano rod tube to transport my rods for every trip – it’s affordable, fits several rods, and is adjustable depending on the length you need.

Plano Rod Tube (TackleDirect)

This is the Plano rod tube I use to transport my two rods. It's made it through 8 airline flights now.

Plano Rod Tube (Amazon)

This is the Plano rod tube I use to transport my two rods. It's made it through 8 airline flights now.

Reels

I use Shimano TLD 30IIAs. This was a recommendation from a friend that does some serious marlin fishing in the Gulf of Mexico.

Here’s why the 2-speed reel is great for sailboat fishing. When sailboat fishing under sail and you land a good size fish, you can’t just stop and you can only slow down so much with course corrections. The 2-speed reel lets you use the low gear to deliver more power to the fight.

Check out the youtube video below of the cero mackerel we caught on a 2022 trip to the USVI and Spanish Virgin Islands. We were sailing in 30 knots of apparent wind and had a reef in the main and jib. At the time we hooked up we were sailing at 9-10 knots and were only able to slow down to about 7.5 knots while we reeled it in.

I have the reels spun with 65 pound braided line (braid) and topped with 80 pound mono line. 

Spinning reels are also great – if you come up on a school of mahi-mahi, stop or slow the yacht, and cast some lures out. Keep in mind if you plan to use them for trolling, you won’t be able to have as much line on them as compared to trolling (or conventional) reels.

Shimano TLD-30IIA reel (TackleDirect)

This reel might be oversized for some of the fish you'll catch, but the 2-speed reel will help when you aren't able to take the sails down and have to keep moving.

Shimano TLD-30IIA reel (Amazon)

This reel might be oversized for some of the fish you'll catch, but the 2-speed reel will help when you aren't able to take the sails down and have to keep moving.

Fishing tackle for bareboat charter trip
Prepping some lures and tackle ahead of a bareboat sailing trip

Other equipment for fishing off a sailboat

For my tools and knives, I use BUBBA products. You’ll get their famous non-stick grip and high-quality materials that will within stand the saltwater. These things will last for years.

Filet knife – I highly recommend bringing your own, well-sharpened filet knife. The boat is unlikely to have a knife sharp enough for the job. You also want a blade that is flexible. We brought this BUBBA knife on our recent Exumas sailing trip and it worked great!

BUBBA 7 Inch Tapered Fillet Knife (Amazon)

Razor sharp and comes with the BUBBA non-stick grip.

Exuma fishing tips: filleting a wahoo in the Exumas
Filleting a freshly caught wahoo in the Exumas

Pliers – I use them to help remove hooks and to cut wire leader.

BUBBA Stainless Steel Pliers (Amazon)

These pliers won't rust and they also come with crimper and cutting features.

Casting net – I do not bring one of these, but you can if you are a serious angler and have an idea where to catch them. Some countries may not allow them, so make sure you double check the rules.

Trolling hooks – bring some #7 or #8s, such as Mustad Big Game Stainless Steel. The stainless steel are more expensive, but are resistant to saltwater. You’ll use these hooks to set up your skirted lures and ballyhoo rigs (if you can find frozen ballyhoo).

Mustad Big Game Stainless Steel Hooks (TackleDirect)

These are the sharpest hooks you can find and the stainless steel will help prevent rusting in between trips.

Mustad Big Game Stainless Steel Hooks (Amazon)

These are the sharpest hooks you can find and the stainless steel will help prevent rusting in between trips.

Bait circle hooks – I like Gamakatsu or Mustad #7s. The circle hooks are best for bottom dropping with live/dead bait. The fish is most likely to swallow the bait whole, and the circle hook helps to prevent the hook from getting stuck in deep. Rather, they are designed to hook them in the mouth.

Gomakatsu Circle Hooks (TackleDirect)

These are great hooks to attach some live/dead bait and set on the bottom. Use the Double Dropper Rig (video below).

Gomakatsu Circle Hooks (Amazon)

These are great hooks to attach some live/dead bait and set on the bottom. Use the Double Dropper Rig (video below).

Live bait net – I’m usually able to catch a couple live bait on sabiki rigs each trip. I keep them alive in this Lindy Bait Tamer. 

Catching live bait blue runners with a sabiki rig
Catching some blue runners for live bait slow trolling | We keep them alive in a bait tank
Lindy BaitTamer (Amazon)

This one is right-sized for a bareboat charter and has held up over several trips. You can keep it in the water when you are at anchor. When moving, put it in a bucket and change the water every hour to keep the fish alive.

Gloves – I would consider this optional. We usually have a pair on hand to search for spiny lobster. The gloves can make it easier to handle a fish without the help of a gaff or net.

Sabiki Rigs – for catching bait fish. I usually bring 2-3 since they can get tangled and break easily.

Weights – you’ll want a couple for bottom dropping. The deeper you drop, plan to go heavier.

Swivels – you’ll attach these to your primary line to quickly swap out pre-rigged lures. Look for ~75+ pound rated ball bearing swivels with snap connections.

Wire leader – we attach 2 feet or so of steel leader often when trolling since we catch a lot of toothy fish (barracuda, mackerel, and wahoo). This will help you catch more fish and lose fewer lures. Check out Malin Hard-Wire stainless steel leader. No. 6 to No. 9 will do. Check out this youtube video that shows you how to rig up a wire leader with the haywire twist.

Malin Stainless Steel Leader (TackleDirect)

Attach a copy feet of this leader to your rigs to prevent line breakage from tooth fish (like wahoo).

Malin Stainless Steel Leader (Amazon)

Attach a copy feet of this leader to your rigs to prevent line breakage from tooth fish (like wahoo).

Fishing techniques and the lures to bring

Trolling lines are in the water - this is what our setup looks like

What is the best way to go fishing from a sailboat? These are your best options.

Trolling from a sailboat for bluewater sportfish

Most of our fishing is done when we are underway. It’s fun to always to toss a line knowing something could hit your lure at any time.

This is also the best way to cover a lot of distance, do some offshore fishing, and hook up on some game fish. We also do it in 30 feet of water too!

We bring our own rod holders to clamp on to the railings – not all sailing yachts come with them and the charter company may not have spares.

Amarine Rod Holders (Amazon)

These are an affordable option for clamp on rod holders in case you want to bring your own.

King mackerel caught in Key West
King mackerel caught while trolling with a ballyhoo rig and Ilander lure skirt

We will usually pull one line at the top of the water (or slightly below) and a second 10-20 ft deep using a diving lure.

At the top, we use Iland Ilander Trolling Lures with weighted heads to keep the lure just below the surface. We use the 8 1/4 inch length and I like blue/white, pink, and black/purple. Get a variety! If we have dead bait such as ballyhoo or mahi belly, we will rig the skirt with them.

Iland Ilander lure (TackleDirect)

This is a great all-around surface lure that you can often catch mahi, tuna, and king mackerel with. Blue/white, pink, and black/purple are my favorites.

Iland Ilander lure (Amazon)

This is a great all-around surface lure that you can often catch mahi, tuna, and king mackerel with. Blue/white, pink, and black/purple are my favorites.

Iland Ilander Flasher Series lure (TackleDirect)

Try a couple of the flasher skirts as well - the reflective mylar helps to attract some fish species.

Iland Ilander Flasher Series lure (Amazon)

Try a couple of the flasher skirts as well - the reflective mylar helps to attract some fish species.

Fathom Offshore Calico Jack Slant (TackleDirect)

This Fathom lure has a tapered nose that creates great swimming action. It also comes pre-rigged on 12' of mono and includes a stainless steal hookset.

Check out this video on how to rig a ballyhoo for a skirted lure.

For the second rod, we’ll use an artificial diving lure. I like the Rapala X-Rap Magnum and the Yozuri Bonita (look for them in 5-6 inch sizes). They have great action and will dive 10-20 feet below. These are your best bet for catching wahoo.

Yozuri Bonita lure (Tackle Direct)

This has been my most successful diving lure recently, and I caught my first wahoo with it. In 6 3/4 in size, try the Flying Fish, Red Black, and Purple Black.

Rapala X-Rap Magnum lure (Tackle Direct)

Try these in a variety of depths from 15-40 feet. I like Hot Pink, Bonito, and the Green Mackerel colors.

Shark bait in the Exumas
Yo-Zuri Bonita lure (Flying Fish) on a fish that we didn't reel up fast enough!

Experiment with distances – we like to mix it up, and there is no perfect formula. We usually put one line ~75 feet out and the second ~125-150 feet behind the sailboat. You can mark the line with a sharpie to help you quickly get lures back in the water after checking them.

If you notice lots of sargassum seaweed in the water, check those lures frequently and clear them if necessary. While this can be frustrating, the good news is that mahi mahi like to hang out under seaweed lines.

Catching sargassum
This is going to happen to you! Check those lines often.

Casting for mahi-mahi or tuna on the surface

This technique has worked for us a couple times. I also see it successfully done all the time on deep sea fishing charter videos such as StanzFam.

The idea is that while trolling in deeper water, you might come across a school of mahi or tuna. What do you look for?

  1. Birds or a disturbed water surface. This usually means the birds and fish are attacking a bait ball. Go join in on the action! They are in a frenzy and will eat anything.
  2. Mahi-mahi love to hang around weed lines or other floating debris. It is said they don’t like the sun very much. Get close to investigate – you can often see them in clear water.

Stop the boat, toss in some lures, and quickly retrieve them with the reel. This is best done with a spinning reel, but it can work with conventional reels as well. Bring a couple popper lures such as the Rapala Magnum Explode.

If you have live bait, even better!

Here’s a variation of this technique: you just caught a mahi. If you can stop the sailboat, see if it’s friends come to investigate. They sometimes do!

Mahi hook up in the Virgin Islands
Schoolie mahi-mahi caught on a recent trip along a weed line using an Ilander lure

Bottom dropping for reef fish species

Occasionally we’ll stop over a reef and drop a couple lines down to target snapper and grouper. You can even use this technique when at anchor.

We use two hooks on a dropper loop knot and put on some live or dead bait (even if it’s a piece of raw chicken). This video is a great overview of how to tie the knot.

Drop it down and wait for that monster grouper to hit your line!

This technique is hit or miss when sailing. Most fishing boats or fishing charters that use this technique have a sonar fish finder to help them target the fish. Doing it on a sailboat is somewhat of a guessing game, but it has worked for us before. Try and find something with good bottom structure if possible.

Jigging for bottom fish

This technique also targets bottom fish. Drop your jigging lure and let it sink close to the bottom. Once it’s down, pull up quickly once or twice and then let it sink back down. You can also try this in different directions.

For lures, Tady Lures are a great option. I also like Berkeley Fusion Bucktail Jigs – try the 3 ounce version in pink colors.

Little tunny caught trolling near Key West
Little tunny we caught trolling in ~40 feet of water

Where to fish while sailboat fishing

The obvious answer for me is: anytime we are sailing or moving the boat!

If you are trolling in less than 60 feet of water, you are likely to only catch mackerel, barracuda, and potentially some reef fish like mutton snapper.

To turn your sailboat into a sportfishing boat, let’s head for deeper water. I like to use the Navionics Boating App to help plan our routes. The Sonar Chart and Relief Shading layers help you pinpoint bottom structure and shelfs where the water quickly drops off.

You can have a lot of success trolling over bottom structure – anywhere that might provide a habitat to fish. Where there are small fish there are sure to be bigger fish. Also look for non-dangerous wrecks on your charts.

Drops are where the water can quickly fall of from 100 feet to thousands in a short distance. Troll back and forth over this if it will fit in your itinerary. The BVIs, Spanish Virgin Islands, and Exumas all have drops that you can fish during your charter trip.

The picture below is from our sailing trip to the Spanish Virgin Islands where we had a great fishing experience. We caught mahi-mahi, mutton snapper, yellowtail snapper, king mackerel, barracuda, and more. We also did pretty well on a recent bareboat trip to Key West.

Each pin represents a fish caught during that morning we sailed around the eastern end of Vieques. We weren’t able to reach the drop farther south (black and purple shading) due to sailing conditions (the trades were really blowing), but we trolled over the shelf drop and other bottom structure.

Fishing route in Vieques
Trolling route around the shelf area at Vieques in Puerto Rico | Pins represent fish we caught (source: Navionics)

We've caught one, now what?

Well first, get it on the boat!! Our setups described above are usually strong enough to pull the fish straight up onto the steps on the back of the pontoons of our catamaran. We don’t usually worry about the line snapping

If you are sure you’ve landed a keeper, you can also grab it with a gaff to make sure you don’t lose it at the boat. I have not seen many of these on charter boats, but you can ask for one if you rent gear.

For hook removal, we simply use a pair of pliers and gloves. The goal is to get that fish back in the water as soon as possible if it’s catch and release.

How to fillet your fish

I think the absolute best resource to learn is by watching videos. Captain Nick Stanczyk is the expert I turn to. Check out his youtube channel StanzFam. He usually filets fish at the end of every episode, and the videos are really fun to watch.

Filleting a mahi mahi caught in the Virgin Islands
Fileting a mahi at the swim ladder

These are the fish that we would keep if caught:

  • Mahi-mahi
  • Tuna (yellowfin or blackfin)
  • Wahoo
  • Snapper
  • Grouper

There can be some varieties of these, so just be sure you are keeping the good eating ones. For example, a little tunny looks similar to bonito, but are not good eating at all. Check out my guide to the different types of fish in the Virgin Islands. Most of these fish can be caught all throughout the Caribbean.

If you are fishing in areas with ciguatera poisoning, double check local guidance before eating any reef fish.

We always bring supplies to make fish tacos and ceviche (yellow tail snapper is great for this). Simply grilling up some filets with olive oil, garlic, and lemon is also hard to beat.

Fresh caught ono poke bowl
Fresh ono (wahoo) poke bowl from our recent Exumas trip

If you’ve enjoyed this post and are new to bareboat charters or sailing vacations, check out our starter guide here.

Thanks for reading my post about sailboat fishing! If you enjoyed it, please subscribe or check out some of my other articles, like this one about the fish of the Virgin Islands.

Top 10 Mistakes to Avoid on a Yacht Charter Trip

mooring mistake with a single line through the pennant eye

Photo: catamaran with one line to secure to the mooring ball. This method can easily break the line and cast the yacht adrift. 📸 Sean O’Leary

We all make mistakes.

That’s part of becoming a seasoned yacht charter skipper.

But, want to get a head start? Read these and you’ll be ahead of 75% of other skippers.

I also suggest you pick up a copy of the Smarter Charter – lots of good practical chartering advice. I usually give it a scan through as a review before my next trip.

These are my top 10 mistakes to avoid on your yacht charter trip, some of which I’ve had to learn the hard way.

  1. Arriving to your anchorage too late
  2. Entering off-limits, red lined areas
  3. Running a single line through the mooring ball
  4. Not conserving water
  5. Forgetting to pull the dinghy line in when mooring
  6. Ignoring weather reports
  7. Sticking to a planned itinerary
  8. Leaving your fenders out
  9. Letting your engines run unattended
  10. Racing through a mooring field
Cane Garden Bay | Read about an incident below that happened here as the result of arriving too late

Arriving to your anchorage too late

Don’t be that crew that pulls into the mooring field while everyone else is relaxing over a sundowner, or worse, after dark.

Most yacht charter trip contracts require you to be anchored or moored at least 1 hour before sunset.

There is good reason for this.

Arriving before daylight begins to fade allows you to safely navigate through the approach. This matters if you have to pass through a channel and identify the markers (such as Cane Garden Bay or North Sound). Or, you want to be able to see where you are dropping the hook – pick the sandy patch, not the coral.

Additionally it gives you time and the visibility necessary to inspect your mooring ball condition or to dive on the anchor.

What can happen if you arrive to your anchorage too late

Here’s a real world example of what can go wrong from an incident that happened at Cane Garden Bay in 2020:

  • The crew of a Helia 44 arrived after dark, tied off to a mooring ball, and then went ashore for dinner or drinks
  • The mooring ball they tied off to? A private, ill-maintained ball not designed for a 44 foot catamaran. If they had arrived with more daylight, they likely would have noticed it was not a regular ball
  • When they returned on their dinghy, the boat was missing 😮 The yacht had broken loose and went adrift. Somehow no one noticed and it drifted past the reef
  • Luckily, it was later recovered off the north shore of St. Thomas, USVI
  • The crew learned an expensive lesson and had to pay a hefty fee for the recovery

Having a backup plan

Another reason to arrive early? What if your Plan A falls through? What if there are no mooring balls available?

You need enough time to be able to execute your backup, Plan B.

This yacht entered the red lined area between Beef Island and Little Camanoe in the BVIs
Off-limits passage between Little Camanoe and Beef Island
This red lined areas has claimed more charter yachts than anywhere else

Entering off-limits, red lined areas

Red lined, off limits areas present serious hazards to yacht charters.

Reefs, shallow water, and exposure to weather conditions such as north swells, to name a few.

Don’t believe me? Check out Groundings of BVI for some examples of the severe consequences that can result.

It’s simple.

Pay attention during your charter briefing and stay out of areas that are red lined. You can read about the more notorious BVI red lined areas here.

Running a single line through the mooring ball

I see this happen often with beginners.

When tying off to mooring balls, they run one line, through the pennant eye, and then tie it off to the cleat on the other side of the vessel..

This is bad practice.

As the yacht swings on wind and tide, the pennant eye acts like a saw on the line. Eventually it can break it loose, setting your yacht adrift.

Better idea? Run two independent lines, one from each side or pontoon. Secure the lines back to the same cleat on either side.

Check out my charter beginners guide where I posted a video about how to properly pick up a mooring ball.

The consequences of your yacht going adrift? Find out what happened to the Sunsail catamaran Panema.

Not conserving water

Ever heard of a navy shower? 

Or better yet?

We like to bring reef-safe shampoo and take a sea shower off the back of the catamaran. Do your final rinse with fresh water.

Many yachts have water makers these days, but not all of them. Relying on a water maker to work for your whole trip is, well, playing with fire.

It’s no fun needing to pull into a marina to fill up your water tanks when you could be offshore catching fish or lazing on a beach.

Brief the crew: use water sparingly. Don’t take long showers. Do dish washing heavy lifting with sea water if you can.

If your water maker is working and you have just a couple days left with full tanks? Go wild! You are water rich.

Forgetting to pull in the dinghy line when mooring

Yup. I’ve done it.

I’ve wrapped the dinghy line around a prop.

Not a big deal, but I did have to spend 30 minutes diving on the prop to cut loose the line. If this happens you should also inform the charter company since there could be unseen damage to the saildrive.

Just make this one part of your crew’s anchor/mooring routine. 

Have someone responsible for pulling in the dinghy so there is minimal slack in the line, every time.

Virgin Islands NOAA Forecast Zones
NOAA marine forecast zones for the Virgin Islands and Puerto Rico

Ignoring weather reports

On my first trip to the BVIs, I didn’t pay attention to the weather reports at all during the trip.

That was a big mistake.

Luckily, we had the consistent, beautiful BVI trade wind weather that is often present.

But what if a north swell was running? I could have been caught off guard.

Take it a step further beyond the marine forecast printout you’ll receive (sometimes) at your charter briefing. Check the forecast resources everyday. In most charter destinations, cell phone coverage or wifi should be available most days.

If you are sailing during hurricane season, be even more vigilant.

I talk about which resources I use for by bareboat charter trips in my BVI marine weather post.

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Dodging squalls on the way to the Dry Tortugas on a bareboat charter trip
A squally day on a recent trip to the Dry Tortugas, the least of the challenges we encountered

Sticking to a planned itinerary

Be. Flexible.

The boat is going to have a maintenance issue.

Someone of the crew might be seasick.

A day or two of thunderstorms and squalls might interrupt your plans.

On my recent yacht charter trip to Key West to the Dry Tortugas, we had a lot of issues to deal with, but we adjusted. That’s part of the territory with yacht charter trips.

  • We had to swap boats after our first day
  • The AC didn’t work in August in South Florida ☀️☀️☀️, so we moved the boat to a better slip for a breeze
  • We added an extra day to the trip so we could make it all the way to the Dry Tortugas
  • Lost a day of exploring in the Dry Tortugas, but it was better than not going at all
  • Lastly, we grabbed a hotel room the last night, well, because of ☀️☀️☀️

One of your jobs as skipper is to create a happy ship. Shake off the disruption, whatever it is, and adjust the trip as needed. Even if it means you have to cut out a favorite stop or destination.

Another good piece of advice? Don’t try to do too much on your first day. Have a short and easy passage. Let the crew get adjusted to the yacht. We also rarely get out of the marina as early as we’d like to.

Leaving your fenders out

Ok. This really isn’t that big of a deal.

But.

There is no better way to identify yourself as a beginner to other yachts 😎. Don’t be that skipper!

Letting your engines run unattended

It might be tempting to charge the batteries in idle while your ashore enjoying a specular meal.

No one likes to hear the engines running.

But seriously, don’t do that. We don’t run any systems – engines, generator, or water maker, when we are not on the yacht.

Here’s an example of what can happen if you don’t take my advice.

Anegada Setting Point anchorage and mooring field
The somewhat crowded mooring field at Setting Point, Anegada

Racing through a mooring field

Don’t try and race another yacht to try and pick up the last first come first serve mooring ball at Cooper Island.

It’s dangerous, and not worth it.

Lots of people, myself included enjoy swimming off the back of the boat and would love it if you don’t run us over 🤝.

Thanks for reading my post about the top 10 mistakes to avoid on a yacht charter trip and making it all the way to the end! If you enjoyed it, please subscribe or check out some of my other articles, like this one about my favorite BVI anchorages.

Is White Bay in Jost Van Dyke too Dangerous to Anchor?

painkillers at the soggy dollar bar in white bay jost van dyke

There might not be a more idlyllic British Virgin Islands experience than anchoring in front of the Soggy Dollar Bar at White Bay, Jost Van Dyke, swimming ashore, and ordering a Painkiller from the bar.

But for me, those days might be over.

Why?

It’s becoming an overcrowded anchorage with increasing amounts of reckless behavior from inexperienced “credit card captains”.

Many charter companies now redline this anchorage as an off-limits, no-go area.

White Bay can be dangerous for other non-man made reasons, but a prudent skipper can safely mitigate those risks.

Now let me be clear: I am not recommending you avoid White Bay and the beloved beach bars that line it, such as Coco Loco, Soggy, Hendo’s, and Ivan’s Stress Free Bar.

I just think there are better ways to experience this wonderful piece of paradise.

What is the White Bay anchorage like?

Why is White Bay becoming so popular?

Alternatives to anchoring at White Bay

aerial view of white bay jost van dyke
Overview of the White Bay anchorage with the east and west side

What is the White Bay anchorage like?

This famous British Virgin Islands anchorage is split in two – an east and a west side. The west side being the more popular crowded area in front of the Soggy Dollar Bar.

Narrow channels mark the entrance to each side, with a reef restricting safe access from anywhere else (although ill-advised skippers have been known to bypass the markers).

Inside the anchorages, it can get quite tight with little swinging room on a busy day.

Crowding leaves little margin for error. If a boat drags anchor it can quickly turn into bumper cars. Take this recent incident for example.

Video of unmanned 50 foot catamaran motoring around the White Bay anchorage.

Here’s what I think happened based on comments I’ve read about the incident:

  • Skipper and crew all went ashore and left the engines in idle, presumably to charge batteries (you should never do this!!)

  • A jib sheet was left improperly secured

  • At some point, the sheet became loose and began flapping in the wind as the sail unfurled from the wind

  • The sheet wrapped around the throttles and put the engines in gear

  • The cat was tied off to a mooring ball, and it motored in circles until it pulled out the screw, causing the incident you see in the video

It’s extremely fortunate that no one was hurt. I’ve often swam in those waters to and from the beach.

This isn’t the only accident that has occurred, just the most recent.

Here’s another two incidents that recently occurred, at the same time. The catamaran in the background anchored in the channel, realized the mistake, and then proceeded to foul the anchor chain with the channel marker.

The monohull appears to have grounded on the reef and is attempting to get pulled off by the dinghy.

Grounding in White Bay Jost Van Dyke
A grounding and another boat that fouled the channel marker
swimming at white bay jost van dyke
The action settles down by the evening at White Bay as the day trippers depart

So have I anchored overnight in White Bay on the west side? Yes, so how did I get comfortable with it?

  • Light winds were forecasted: 5-10 knots

  • No thunderstorms were forecasted

  • I had planned to leave for Great Harbour if it became too crowded

  • I visited in late May when White Bay is less busy than usual (although today that might not be the case)

Will I do it again? Probably not anymore. While it does thin out in the evening, I prefer not to deal with the daytime party madness.

White Bay anchorage at Jost van Dyke
Here's where I anchored in front of Hendo's on the west side on my last trip | Only two boats remained overnight, the powercat is on a mooring ball

Weather conditions that affect White Bay

Thunderstorms

If any thunderstorms are forecasted for the area, even an isolated squall, it’s best to avoid the anchorage overnight.

If a squall rolls in and you drag anchor, it’s very unlikely you will have time to get to the helm station and take action before being grounded on the beach or reef.

Northerly ground swells

While south facing, northerly ground swells from distant storms can still wrap there way around the west side of JVD and make the anchorage uncomfortable. If severe enough, these can also cause a similar condition where the anchor drags.

I talk more about this weather feature in my piece on BVI weather and marine forecasting.

Backwinding

If the easterly trades shift more into the NE, it is possible to get backwinded at White Bay. This isn’t a good situation since your yacht is already quite close to the beach.

Basically, strong trades (15+ knots) blowing over steep terrain can create a vortex where at the surface, you actually experience winds opposite of those that are prevailing. In this case, you could experience SE winds which could push you towards the shore.

If you don’t have enough swinging room (which is always a challenge in White Bay), you could ground on the beach.

Again, see my BVI weather post if you want to learn more.

palm-tree
BVI Charter Frequently Asked Questions

Why is White Bay Jost van Dyke becoming so popular?

Every year though, it seems White Bay and the Soggy Dollar grow in popularity. With that comes excessive crowds, drinking, and partying.

The islands are back with a vengeance following the devastating storms of 2017: Hurricane Irma and Maria. Many popular resorts have re-opened and visitor levels have rebounded, despite rollercoaster travel restrictions from Covid.

The Soggy Dollar Bar is gaining renown as one of the top beach bars to visit in the Caribbean. They routinely make the top 10 lists, aided by their claim to fame of having invented the Painkiller drink in the 1970s.

They even have their own rum brand now.

Needless to say, the word is out.

When cruise ships are in town, White Bay is a popular powerboat charter destination. Boats also speed over from the St. John or St Thomas, USVI to spend the day at White Bay Jost Van Dyke. Great Harbour, next door, has a customs office, making checking in to the BVIs efficient.

These additional vessels weave their way between the anchored sailboats and further crowd the anchorage.

View from the dock at Foxy's Taboo at Diamond Cay

Alternatives to anchoring at White Bay Jost Van Dyke in the BVIs

The great news: there are many!!

Utilize the mooring field at Diamond Cay near Little Jost Van Dyke

This would be my recommendation and the approach I’ll take next time I visit the BVIs (hopefully soon, it’s been 3 years!)

It’s easy to arrange for a taxi for a quick 15 min day trip to White Bay.

Staying here also allows you to kill two birds with one stone – you are a short hike away from the Bubbly Pool one of the most popular attractions at Jost Van Dyke. It’s a half mile hike. Bring your swimsuit to enjoy the pool at hightide as the waves crash through.

If you want a more laid back beach vibe, visit B-Line with your dinghy. Foxy’s Taboo is also a great option for a cocktail or dinner.

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bubbly pool jost van dyke
Bubbly pool at Jost Van Dyke

Stay nearby at Great Harbour or Little Harbour

Next door, Great Harbour and Little Harbour are also safer alternatives.

Great Harbour now has Boaty Ball moorings, so you can reserve one during the busy season if you are worried about availability.

Again, it’s easy to arrange for a taxi. You can also walk if you’d like (the views are great, 1.5 miles from Great Harbour) or dinghy over to the bay in settled weather. If there are strong trades blowing, you might have a wet ride back though!

Staying in one of these bays gives you additional options for dinner. If in Great Harbour, you can also visit Foxy’s in the evening, another establishment that has gained in popularity similar to Soggy.

white bay east side jost van dyke
View from the east side of White Bay | Notice the nearby cruise ship!

Pick up a mooring ball on the east side of White Bay

If you want to stay close to the action (and White Bay is not redlined by your charter company), there are several moorings on the east side. Pay for it ashore at Ivan’s.

The east side of the bay is always less crowded, and quieter. Plus, it has more room than the west end.

You can dinghy over to the other beach bars, or simply walk along the shore.

Palm Tree that was commemorated for us following a donation to the Hurricane Irma community fund.

I love White Bay and it will always have a special place in our heart with the memories it has created over the years. We will continue to be patrons of White Bay JVD, but our dollars might be dry the next time we visit!

If you want to learn more about the British Virgin Islands or read other articles I’ve written about this destination, check out my British Virgin Islands page.

Sailing the Exumas: Bahamas Bareboat Charter

Wahoo caught on the drop in the Exumas sound

We returned to go sailing the Exumas on a Bahamas bareboat charter for the first time since 2018. It had been too long for one my favorite sailing destinations. It was our first time sailing in December, so I was also looking forward to that!

The island chain in the Bahamas had everything our crew was looking for in an Exuma Yacht Charter: solitude, natural beauty, fantastic sea life, stunning anchorages, and great fishing. We cashed in on each of those this trip.

For a week-long trip, we sailed just the northern half of the Exumas and did a loop – our turnaround point was Staniel Cay.

This is a long post with lots of pictures –  I hope you enjoy! You can also check out our Exumas Cruising Guide to learn more about planning your next Bahamas yacht charter trip here.

Table of contents:

Exuma weather gods were on our side

Route planning for Yellow Banks crossing
Close hauled on our forecast for the first day Yellow Banks crossing (source: Predict Wind)

I began weather watch in October to follow the patterns. I was surprised to learn that cold fronts, albeit weak, had already begun to sweep down and make their way through the Bahamas. Yikes.

Despite this, we got lucky and didn’t have to deal with one! Very lucky for this time of year. This allowed us to keep our planned itinerary without any disruption.

Winds were settled for the entire trip: 10-15 knots varying from the NE to the SE. Perfect!

No rain the entire Bahamas bareboat charter (of course, because I bought a new rain coat before we left).

Snorkeling clarity was outstanding thanks to the steady easterlies that blessed us.

Bali 5.4 in the Exumas on a bareboat charter trip
You will have plenty of space to spread out on this sailing yacht!

The Bahamas bareboat charter catamaran - Bali 5.4

We were originally booked on a Lagoon 46. However, a month before the trip, the yacht charter company reached out and let us know that it was going to be delivered late. Instead they were upgrading us to a Bali 5.4 – the same one they had on display at the Annapolis Boat Show (Yepa II).

This thing had all the bells and whistles – huge hangout area up top with drink fridge, blue underwater lights, hydraulic swim platform, generator, watermaker, etc. Here’s a more in-depth boat review I put together about it.

The crew’s verdict is that this is the best sailing catamaran we’ve ever been on.

Bali 5.4 blue lights in the Exumas
The underwater blue lights were a lot of fun - we saw lots of fish and a few sharks

We really enjoyed the top deck lounge area that integrated the helm station – plenty of room for everyone to hang while cruising during the day. This is where we spent most of our time

Our version had 5 full cabins and two singles in the front (presumably for a captain and hostess).

She sailed fairly well – we topped out at around 7 knots with 10-15 knot winds on a broad reach. Closer to running with just the mainsail up, we were cruising at 6 knots.

Bali 5.4 downwind sailing
Easy downwind sailing in ~10 knots

What surprised me, was how speedy she was through the water under motor. Both engines at 2,500 rpm gave us 9-10 knots! Most cats I’ve been on have only done 7-8 with this much power.

It’s worth pointing out that the bow is quite high off the water – our crew had to laydown under the lifelines to reach a mooring ball – not ideal. Just make sure your boat hook is long enough!

This added speed came in handy on our first day (see below!).

The Exumas sailing itinerary: 7 spectacular days in the Exuma Islands

Arrival day

It’s always easy traveling in and out of Nassau. We love that we can connect directly from the US on a short flight and have plenty of daylight left at the marina for check-in.

We opted to use the Dream Yacht Charter (DYC) provisioning service for the bulk of our food and beverages. We supplemented with a quick trip to Solomon’s for some essentials that weren’t on the list. It’s less than a mile from Palm Cay Marina.

Palm Cay hasn’t changed much in the three years since we’ve been there, except for one new condo building. Lots of ongoing construction, but nothing too disruptive or bothersome.

Palm Cay sunset, the Exuma bareboat charter base
Lots of construction underway at Palm Cay

We were able to check-in a bit before the prescribed time (5:00pm). All was well until they informed us that the previous charter group ran aground and damaged both the rudders!! 

So much for that day-of-arrival inspection we paid for (we were reimbursed).

DYC was on top of it and had it being repaired overnight. The rudders were due back at 8:00am the next morning, after which they would need a diver to assist with the reinstall.

Having been through problems (and charter company promises) like this before, I was preparing to spend our first full day in the marina.

We enjoyed a good meal by the pool at the Pink Octopus and threw down an extra painkiller since we were no longer departing first thing in the morning.

Catamaran Christmas lights
Getting in the holiday spirit - our first time sailing in December

Day 1 - Yellow Bank crossing to Ship Channel Cay

To my great astonishment, the rudders arrived at 9:00, and they were re-installed by 11:30!!! 

While they were completing the repair, we chased down some loose ends (snorkel gear, rod holders, etc.) and said hello to a couple crewmembers of La Vagabonde.

We quickly topped off the fuel tanks and were off to go sailing the Exumas!

Amazing, and I couldn’t believe it.

sailing the Exumas
Goodbye Nassau - off to a week in paradise!!

Winds were less than 10 knots and on the nose. So with the late departure we were most certainly motoring. No biggie. We’ve learned to be flexible on these week-long trips.

It was a calm, gorgeous day and the coral heads were easily seen crossing the Yellow Banks, despite being somewhat later in the day than you would typically like.

We enjoy checking out new anchorages, so we pointed for the southern end of Ship Channel Cay. Along the way we hooked a couple barracudas and kept one for bait.

Barracuda catch in the Exumas
First fish of the trip - barracuda of course in 20 feet of water

With our 9-10 knots of speed, we even arrived with time for some paddleboarding and a cruise around the area in the dinghy.

We were the only boat in the around, so we enjoyed our first sundowner in complete solitude – perfect.

Ship Channel Cay paddleboarding
The ladies using the SUPs in perfect conditions
Ship Channel Cay anchorage Exumas
Day 1 at Ship Channel Cay; sure beats getting stuck in the marina on your first day

Day 2: Trolling down to Pirate's Lair in the Exuma Cays Land and Sea Park

We decided to take our time on our second day and make it as far south as we could – we would decide later where to drop the hook. No set destination to rush us.

Before leaving, we snorkeled the nearby coral heads. There was some great sea life to include a few rays and turtles. Alan even used the Hawaiian Sling to spear a lionfish, an invasive species. We take shots at these whenever we can. 

We had ideal wind conditions out of the NE for a southerly passage on the deep Exuma Sound side, so we went to do some sailboat fishing and hoped for some wahoo! Used the wide Ship Channel Cut to the north to head into deeper water. Check out my Exumas fishing tips if you want to learn more.

Alas, we had several good fish on that we lost, and of course caught several ‘cudas in some shallower water before we entered the park boundaries.

We chose to pull in to the Pirates Lair mooring field at Warderick Wells. It’s easily accessed from the deep side. In the cut, your only option is to use the mooring balls (I counted 4), the tide rips through here! I’ve heard anchoring isn’t allowed in this area anymore, although in the past it was doable at Hog Cay.

Pirate's Lair Warderick Wells Exumas
The tide rips at the Pirate's Lair mooring field in the Exuma Cays Land and Sea Park

The crew crushed it and we picked up a ball on the second try despite that ripping tide.

Ashore, we made our way through the cabbage palms to the fresh water well and home of the Pirate’s Lair. There’s not much to see, but it’s an interesting area to explore.

Pirate's Lair Warderick Wells Exumas
Ladies at Pirate's Lair on Warderick Wells
Pirate's Lair Warderick Wells Exumas

Now if you’re a purist, you may not like this – but we bring along a projector, connect it to the yacht’s sound system with bluetooth, and do Master and Commander movie night on the big screen (bed sheet). It’s our favorite movie and being aboard makes it even more magical.

Give it a try! We thought the Pirate’s Lair was an ideal setting to enjoy it on this trip.

Watching Master and Commander afloat
Watching Master and Commander afloat on the big screen
Pirate's Lair Warderick Wells Exumas
Sunset at Pirate's Lair looking at the north entrance to the anchorage

Day 3: Turnaround point at Staniel Cay

This was our last day heading south on the yacht charter trip, before we would turn around and make our way back up the Exuma chain.

We exited Pirate’s Lair to the southeast and weaved our way through the various small cays aptly named after famous pirates – Teach Rock (Blackbeard), Read Rock (Mary Read), and Bonney Rock (Anne Bonney). It’s tight, but the route is well marked on charts.

Navigating Warderick Wells cays
Narrow passage to exit southeast of the Pirate's Lair

Again, we headed out to the drop for some fishing and passed by Halls Pond on the way to blue water. We had to stay well offshore due to the Exuma Sea Park boundary.

Nothing special for the fishing report – all the action on this trip came on Day 6.

Came back in through Big Rock Cut and anchored at what’s known as West of Thunderball by Garmin Active Captain.

Approaching Staniel Cay anchorage
Approaching the anchorage near Staniel Cay with Thunderball Grotto just off the starboard bow (not visible in picture)

We didn’t time slack tide correctly, so snorkeling Thunderball Grotto was definitely a workout! Great experience as always.

While I would prefer to avoid the chaos over at Big Major’s with the swimming pigs, we compromised and settled for a quick dinghy drive by.

We went ashore for our only dinner out of the trip at Staniel Cay Yacht Club. We decked out in our best Christmas attire and were instantly recognized by the other Texans ashore by our Buccee’s ugly sweaters. Great times were had with those Texans…

I’ll blame the famous SCYC peanut coladas, but when we returned to the protected dingy beach, it was gone! A quick scan of the area found it floating nearby – oops! We had pulled it all the way up, but the rising tide got us. Next time, we’ll tie off.

Staniel Cay Yacht Club
Staniel Cay Yacht Club bar

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Day 4: Sandbars, pristine beaches, and sharks

We rubbed our bleary eyes and motored to Sandy Cay for a lunch stop at one of the best sandbars in the Exumas. It’s an easy anchorage on the west side of the cay.

The scuttlebutt from our evening at SCYC was that the day before a billionaire’s yacht was set up at Sandy Cay. We didn’t have quite the staff and water sports equipment, but it was awesome nonetheless!

Sandbar at Sandy Cay on a Exuma yacht charter
Aerial shot of the great Sandy Cay sandbar
Exumas sandbar
Sandbar at Sandy Cay, Exumas

We could have spent all day swimming, beaching, and lounging in this setting. On the hill on the southern end of the island, there’s a covered cabana which gives you a decent view of the area.

After lunch, we threw up the sails for a quick passage to Compass Cay (outer) anchorage.

We heard that Crescent Beach on Compass Cay is one of the finer white sand beaches in the Exumas, so we went ashore to check it out.

After paying the landing fee at the marina, it was only a short 10 minute hike to the beach. It was late in the evening so we didn’t get in the water, but what a gorgeous beach!

We hung out on the beach cabanas, cracked a few beers, and enjoyed the view of a full rainbow to our east.

Crescent Beach Compass Cay
Swinging at Crescent Beach, Compass Cay Exumas
Hiking on Compass Cay Exumas

Compass Cay is known for the nurse sharks that hang out in the marina. Back at our yacht, one of them paid us a visit and hung out for nearly an hour.

Compass Cay shark

Day 5: An abandoned plane, caves, and some downwind sailing

The next morning, we worked our way north along the channels to the west of Compass Cay and then navigated through several coral heads to the U-shaped bight at Fowl Cay.

I love these seemingly hidden gem anchorages. You’ll find them all over on an Exumas Bahamas bareboat charter. This one is fairly exposed and I wouldn’t want to be here overnight in strong winds. It makes for a fantastic lunch stop though!

Fowl Cay is a private island, and they definitely make sure you know it – many signs that say Private Property, especially over by the abandoned prop plane.

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Want to learn more about an Exuma yacht charter? Start here.
Fowl Cay anchorage Exuma Bahamas
Fowl Cay anchorage just south of the Exuma Land and Sea Park
Abandoned plane at Fowl Cay Exumas
Abandoned prop plane at the bight

While the ladies lounged, Alan and I tried our hand with the Hawaiian sling on the reefs along the northern edge of the anchorage (you can see it it the drone picture). I missed a nice sized grouper but we were able to spear another lionfish.

It was only appropriate that we made lionfish ceviche for lunch (here’s our recipe) – so good! If you are careful with the spines, you’ll be rewarded with a really great tasting fish.

Catching lionfish in the Exumas
Fresh caught lionfish ceviche
Lionfish ceviche - delish!

Fowl Cay is also an excellent day spot because it puts you in perfect position to dinghy over to Rocky Dundas, the two tall rocky islands just to the north. Conditions weren’t perfect to explore the caves – wind waves from the easterly trades, decent current, and a high tide.

Despite that, we were all able to dive under and check out the impressive caves with the stalagmite and stalactite formations.

The wind backed into the southeast after lunch, so we raised the main for some easy downwind sailing on our way to Shroud Cay.

Easy downwind sailing in the Exumas
Downwind sailing north in the Exuma Bank with wind out of the southeast
Rain shower in the Exumas
The only rain shower we saw the entire trip

We avoided the busy mooring field and anchored in Fresh Water Bay to give ourselves easier dinghy access to the mangrove river the next morning.

Fresh Water Bay at Shroud Cay
Fresh Water Bay at Shroud Cay and the mangrove river in the background

Day 6: River adventures at Shroud Cay and wahooooo outside Sail Rocks North

Believe it or not, our entire itinerary was coordinated around being at Shroud Cay on this day. It was the only day a slack tide occurred during the daytime hours.

We launched the dinghy on a rising tide, an hour before slack tide. This timing allowed us to ride the water slide at the other end of the river.

Passing through the mangroves, we saw a few turtles and rays, but no resting nurse sharks.

Mangrove River at Shroud Cay
Riding the mangrove river at Shroud Cay to Camp Driftwood

The hike up to Camp Driftwood was fun, but our favorite part of this excursion was riding the water slide with the outgoing tide.

I wish we could have stayed longer, but we had some ground to cover on our way north. It was also our last day for serious fishing on the drop, so we had to get to work.

Atop Camp Driftwood
View from the Camp Driftwood hilltop
Riding the waterslide at Camp Driftwood
Riding the water slide at the end of the Shroud Cay mangrove river

We passed into blue water at Wax Cay Cut, exited the park boundaries, and got the lines in the water. There is not a moment to lose.

Our fishing spread was one diving lure and a surface Illander skirt lure – rotated and checked for sargassum every 20-30 minutes.

It started slowly, but the action seemed to come all at once.

Something huge hit the port surface lure near Ship Channel Cay – it ran most of the 80 pound braid out and then snapped the line!

It took about 20 minutes to repair the line and get it back in the water. 

Just then, another screamer on the diving lure, a Yo-Zuri Bonita (flying fish). This was the fish we were looking for – a wahoo! It wasn’t huge, but it was a great eating size for the crew.

Northern Exumas Wahoo
Wally the Wahoo caught on the drop in the northern Exumas

About 10 minutes later, on the approach to our anchorage at Sail Rocks North, we hooked another fish. We thought we lost it, until we pulled in just the head of a barracuda – again on that same Yo-Zuri lure. Shark must have gotten it.

Shark bait in the Exumas
Shark bait - bad day for Barry the Barracuda

Sail Rocks North is a special place – you feel like you are in the middle of nowhere on this shoal anchorage. We had 10 knots of wind out of the east and the protection was excellent – very little swell and good holding.

For dinner, we dined on fresh wahoo (ono) sashimi and poke bowls. Can’t beat that!

Fresh caught ono poke bowl
Fresh ono poke bowls for dinner on our last night in the Exuma Islands
Sail Rocks North anchorage sunset
Great sunset to wrap up the trip
Sail Rocks North anchorage

Day 7: Back to Nassau over the Yellow Bank

We always spend our final night of an Exumas trip back in the marina. Makes packing up easier and avoids morning competition for the fuel dock. Less stress all around.

So, we weighed anchor and began the trip back across the Yellow Bank.

It was a relatively calm day that turned glassy as the hours passed – unfortunately, that meant motoring, again.

Glassy seas on the Yellow Bank near Exumas Bahamas
Glassy conditions on our return to the marina meant running the engines

We dropped anchor mid-way for a lunch stop near some coral heads and got a final farewell snorkel in.

Getting back to the marina was easy – pulled into the fuel dock and then had the DYC crew assist with docking the large cat back in it’s slip.

Another successful sailing trip in the books!

Thanks for reading my trip report about sailing the Exumas and our Bahamas bareboat charter adventure. If you want to learn more about the Exumas, especially some of the more popular anchorages, check out our Exumas Cruising Guide. Please subscribe to see more content from me about yacht charter trips!

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Exumas Cruising Guide: Our Favorite Bahamas Sailing Destination

Fowl Cay anchorage Exuma Bahamas

We first visited the Exuma cays back in 2018 on a bareboat charter and wow!! It is nothing like the Virgin Islands where we had done most of our prior sailing.

I mean this in a very very good way – shallow water sailing amidst unbelievable shades of blue, remote and pristine natural beauty, sandbars galore, solitude, and of course – serious fishing.

We are heading back in several weeks for another trip (update – here’s the trip report, with lots more pictures), so this seemed like the perfect time to collect my thoughts on this top-notch sailing destination.

To begin, it is not a place for beginner captains – weather, anchoring, tides, and cuts present unique challenges. It helps to have experience on the water. The British Virgin Islands, for example, is well-suited for a first time sailing trip.

Here’s what you need to know. After you get through the basics, I include a sample sailing itinerary that I would use for a first-time visit to the Exumas. Visit my Exumas page for even more information about this charter destination.

Let’s get to it.

Planning for your Exumas bareboat charter

Palm Cay sunset, the Exuma bareboat charter base
Great sunset at the Palm Cay Marina

One of the benefits of a yacht charter in the Exumas, Bahamas is the proximity to the U.S. mainland. All the major bareboat charter operators are based in Palm Cay Marina in Nassau, New Providence. I’ve chartered with them all and can help you make the right yacht and charter company decision for your next trip. Learn more here.

Many short, direct flights are available from cities such as Houston, Texas and Miami, Florida. You’ll be settled into your sailboat with a cocktail before the sun goes down.

It’s about a 45 minute trip to Palm Cay from the airport. You can either grab a taxi or arrange for a shuttle with your charter company. Palm Cay is conveniently located on the southeast side of the island – a perfect jumping off point to cross over to the Exumas island chain. 

Provisioning

We recommend provisioning with your charter company. They can provide you with a food and beverage list that will have most of what you will need. Expect an occasional substitution as well. When you arrive, your food and beverages will already be aboard your yacht. What’s not to like about that!

If you prefer to do your own shopping, Solomon’s is a well-stocked supermarket located about a mile from Palm Cay. Cars are available from the marina to rent, or you can take a taxi.

Prices are expensive…as they are elsewhere in the Caribbean! Expect to pay ~$50 for a case of beer, for example. Rum is much cheaper though!

Provision well, since there are limited opportunities to re-stock as you head south. Staniel Cay is your best option. Marinas at Highbourne Cay and Compass Cay have smaller stores with more limited selections.

Exumas Bahamas cruising guide resources

The Navionics Boating App is great for planning. Sketch out and research potential routes, fishing spots, and anchorages. ActiveCaptain Community is part of it and is a helpful feature to get additional information direct from other cruisers.

Your charter yacht should come with a recent edition of the Explorer Chartbook – Exumas and Ragged Islands. It’s the gold standard as far as Bahamas charts go.

I often use it before to help plan our sailing itinerary. If you want to purchase it ahead of time, you can get it here:

"Explorer Chartbook - Exumas and Ragged Islands (Amazon)

This is the gold standard for charts in the Bahamas. There should be a copy on your yacht, but you can also pick one up ahead of time for planning.

Stephen Pavlidis puts out a cruising guide with some very valuable information. It has more commentary such as where to go fishing the drop in the Bahamas Sound (he recommends from Sail Rocks to Highbourne Cay).

He also includes his own chart sketches to help with navigation. Keep in mind though, that the most recent edition is from 2015. Better to trust the Explorer Chartbook and electronics. You can pick up a copy here:

"The Exuma Guide" (Amazon)

Although the most recent edition is a few years old, Stephen Pavlidis provides great commentary and advice for your Exumas sailing trip.

Exumas cruising conditions

The Exumas are a long string of 365 islands, stretching over 100 miles from the Sail Rocks in the north all the way down to Great Exuma in the southeast. 

That’s a long way to travel for a week long vacation! It is too far to go all the way down and back in a week. Here are your options:

  1. Explore the northern Exumas, turning around near Staniel Cay (this is what we recommend!). There is so much to explore that you won’t miss out by missing the southern Exumas.
  2. Do a one way trip from Great Exuma to Nassau. This takes advantage or the prevailing trade winds out of the east – enjoy that downwind sailing. It does, however, complicate provisioning since Great Exuma is not as well stocked. You will also need to coordinate extra logistics to travel to Georgetown for the start of your trip.
  3. One way from Nassau to Great Exuma. This makes provisioning easier, but you are more likely to sail to windward.

For the purposes of this cruising guide, we focus on the northern half of the Exumas.

When to sail in the Exumas?

My favorite time of year to go is April-May. Here’s why:

  • Consistent trade winds blow out of the east to southeast, allowing for more settled cruising conditions
  • Cold fronts are not as common.  This means fewer squalls and potential exposure to westerly/northerly winds
  • Days are longer, giving you more time for fun on the water
  • Although early tropical activity can occur, it is far less likely
  • It’s less busy since many of the full-time cruisers have begun to leave the area in preparation for hurricane season

November to December can also be a good time to go – the weather is often pleasant. Keep in mind that cold fronts do sweep down from the west. This can occur as early as October. You’ll need to pay close attention to the weather forecast and have some flexibility with your itinerary. 

In the winter months (January to March) cold fronts march in like clockwork. Be prepared for squalls and winds in excess of 20 knots.

We would avoid the summer months since it can be very hot/humid, the winds are light, and there is always the risk of tropical activity and trip disruption.

Sandy Cany sandbar in the Exumas
The many shades of Exuma blues at the Sandy Cay sandbar

Sailing conditions in the Exuma

Sailing in the Exumas is not for beginners – you need to understand tides, conduct weather planning, and navigate by reading the color of the water. Few mooring balls are available, so you should also be comfortable anchoring almost everywhere (the good news is that the holding is generally very good!).

Wind

The trade winds blow somewhat consistently unless interrupted by fall/winter cold fronts and tropical disturbances in the summer.

In the winter, the trades blow more from the NE. In the summer, they are more frequently from the SE.

downwind sailing in the Exumas
SE winds allowed for some easy downwind sailing as we headed back north

Exuma Bank vs. Exuma Sound

You’ll likely spend most of your time cruising on the west side, on the Exuma Bank. Depths are ~20 feet making for incredible shades of turquoise blue. You also get great protection from the easterly trades, so even with fresh breezes – swells stay to a minimum!

Exuma Sound is the deep side to the east of the Exumas. Reefs mark the edge with many cuts allowing for passage in between. In some places, such as the Dog Cays in the north, the drop plunges to thousands of feet only a couple hundred feet off shore.

The Exuma Sound is where you want to go fishing for the pelagic fish – mahi, tuna, and wahoo. I recommend sailing NW (instead of SE) in the Exuma Sound due to the prevailing trades – you are less likely to encounter swells on your bow. Keep that crew happy!

Exuma cut with a changing tide
Even in calm conditions, opposing tidal flow and trade winds can cause washing machine conditions in the cuts

Tides and Cuts

You will want to pay close attention to the tides due to many shallow anchorages and passages. In general, the tidal range is ~3.5 feet, but can be higher during, for example, Spring tides. In this case, depths at low tide could be below the ones indicated on the charts (MLLW).

I like to print off the latest prediction from NOAA, which provides the tides for Nassau.

  • In the northern Exumas, the tides will be around 20 minutes later than Nassau
  • Around Staniel Cay, you can expect the tides to be about 30 minutes later than Nassau

The numerous cuts between Exuma Sound and Exuma Bank can rip when the tide is flowing. They can be especially treacherous when the wind blows against the direction of the flow. Try and time any passages you make for a period of slack tide.

Charts, especially the Explorer Chart, should be studied carefully. They’ll provide good advice on the preferred cuts to pass through (some are much wider and easier than others).

Anchorages

The majority of anchorages are located with protection from the easterly trades. I’ve found that holding is generally very good with white sandy bottoms. Coral or rock bottoms can be found in areas more affected by the cuts/tidal flow, so keep that in mind.

Use of mooring balls is mainly limited to those available in the Exumas Land and Sea Park. Expect to anchor most everywhere else.

I talk about my favorite Exuma anchorages in this post.

Compass Cay anchorage in the Exuma Bahamas
At yet another secluded Exumas anchroage - this one outside the Compass Cay Marina

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Exumas sailing itinerary: the perfect plan for a week in the islands

Our itinerary plans for 7 days on the water and begins at Palm Cay. As we mentioned earlier, we’ll plan for a “there and back” route with the turnaround point at Staniel Cay.

You might also want to check out my roundtrip, 10-day Exuma sailing itinerary plan.

Day 1: Overnight in Palm Cay Marina

After arriving at the airport, you should be at Palm Cay in under an hour. We usually plan to spend the first night on the boat, but you might also check out the villas that are available.

Unpack, finish your provisioning, and settle in for an enjoyable evening at the Marina. This might be a good chance to dine out since there are not many options available in the Exumas.

The Pink Octopus is a short walk from the marina where you can try some local Bahamian dishes. It’s also located next to the Beach Club where you can grab a cocktail. Check out the pool if you get in early enough!

Day 2: Yellow Banks crossing and Highbourne Cay

Stand up paddleboarding in the Exumas
Enjoying some SUPing in calm conditions after a crossing of the Yellow Banks

Get a start as early as you can! It’s a long day on the water (~35 nautical miles). 

The Yellow Banks is a shallower area mid-way between Nassau and the northern Exumas with many coral heads. But, it’s scarier than it sounds.

With the sun overhead, the coral heads are very easily seen and avoided. Many are marked on charts. If you head for a waypoint south of Beacon Cay, you will also encounter far fewer coral heads. This works for us since we plan to stay at Highbourne Cay on our first night.

It the weather is settled, it’s fun to stop mid-way for lunch on the Yellow Banks. Toss out the anchor in 10-15 feet of water, and enjoy a snorkel of a nearby coral head. Perhaps you’ll find some Bahamian lobster for dinner (lobster season runs August 1 – March 31)! Snorkeling may be difficult if the tides are running – exercise caution.

Highbourne Cay is a convenient first night stop. I like the West Beach anchorage. Avoid the Highbourne Rocks reef on your approach, and anchor in 10-15 of sand.

Near your anchorage, the beach is beautiful and is great for an evening stroll. The Highbourne Rocks also offers great snorkeling.

Crack a beer and enjoy the view – it doesn’t get any better than this. You’ve arrived in paradise.

If you want to venture out farther, you can dinghy ~2 miles to Allen’s Cay to explore the local species of iguanas (this is also a great Day 3 morning activity).

Highbourne Cay marina is a short dinghy ride. They have a store, restaurant, and other amenities. Check out their visitor and snorkeling guide available on the website.

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Day 3: South to the Exuma Cays Land and Sea Park

Pirate's Lair anchorage at Warderick Wells
Enjoying the sunset at the Pirate's Lair anchorage at Warderick Wells

This is another day with a few hours on the water. It’s ~20-25 nautical miles south to the anchorages or mooring fields in the Exuma Cays Land and Sea Park.

If the weather is settled, consider using one of the cuts to enter the Exuma Sound for some deep water fishing. If you go in the fall, it’s a great time to catch some wahoo – my favorite eating fish. Check out our sailboat fishing guide for some advice or my more specific Exuma fishing tips post.

Northern Exumas Wahoo
Make sure you save some time to fish the drop in the Exuma Sound!

As you head south, be aware of the no-fishing zone that protects the park boundaries. The park is strictly a no take zone: no fishing, conching, shelling, or lobstering.

The Sea Park is huge, with over 170 square miles. It’s an ecological reserve and marine sanctuary – you won’t be disappointed by the snorkeling here.

We recommend grabbing a mooring ball in the Emerald Rock mooring field. When you are within range, call “Exuma Park” on channel 9 to check ball availability. Once you’ve taken one notify them.

You can pay the $35 mooring ball fee at the Visitor Center. They also might send around a boat to collect the fees.

The Emerald Rock area is near a couple beautiful white sand beaches and has trail access to the wonderful hiking on Warderick Wells. Make a quick dinghy ride over to the visitors center to snap a picture with the whale skeleton. They can give you a trail map too.

Boo Boo Hill is a popular destination and the highest point on the cay. It’s tradition for cruisers to leave a piece of driftwood behind with your boat’s name on it.

Day 4: Thunderball Grotto and swimming pigs

Staniel Cay Anchorage
Anchorage at Staniel Cay - Thunderball Grotto is the first cay to the left

Continue making your way south towards the anchorage at Big Major Cay.

Sandy Cay is a fun lunch stop close by with one of my favorite sandbars. Anchor on the west side and head ashore for a picnic!

Big Major Cay is the location of the famous swimming pigs. Some words of caution: this is a busy anchorage, so if you’re looking for more solitude, check out Between the Majors anchorage (more advanced anchoring) or Bitter Guana Cay a bit farther south.

Pig beach is fun to see once, but it isn’t a place we’ll need to return. Go get your pictures while swimming with the pigs if you decide to stop here.

The other famous attraction in the area is Thunderball Grotto. It’s an amazing cave snorkel featured in the James Bond movie Thunderball. It’s a short dinghy ride over from Big Major Cay. Otherwise, there are several places to anchor your yacht nearby. Try and plan your visit for slack tide.

Don’t miss your chance to do some re-provisioning and dump some trash. Use the government dock to access two of the nearby grocery stores.

The Staniel Cay Yacht Club is the biggest establishment you’ll come across in this part of the Exumas. We like to plan a meal ashore here, for either lunch or dinner. At a minimum you’ll want to try out their SCYC original – the Peanut Colada.

Note: New as of March 2021, the SCYC now operates 21 mooring balls nearby. Check out the map here. Rates start at $40/night.

Day 5: Back north to Compass Cay

Crescent Beach Compass Cay
We caught a great rainbow on our recent visit to Crescent Beach

Again, if the weather is looking good – head out to the Exuma Sound and do some fishing as you head back north. If the trade winds are from the east, you should have some following seas to please the crew.

Compass cay is a short 1-2 hour sail. You have a few options for anchoring. I like the Compass Cay (Outer Anchorage) since it is less affected by the tides. 

If you want more of a challenge, check out the many options at Pipe Cay. It’s a maze of sandbars and one of the most beautiful areas in the Exumas. 

Nurse sharks at the Compass Cay Marina
Nurse sharks at the Compass Cay Marina

Compass Cay Marina is worth a visit. Get your pictures with the nurse sharks and check out the trails on the cay. Crescent Beach on the east side is said to be one of the finest beaches in the world. Note that you’ll have to pay a landing fee for your dinghy and crew.

Day 6: Shroud Cay and the magical river ride

Shroud cay anchorage and the mangrove river
Shroud Cay anchorage with the mangrove river in the background

Today is a longer day on the water – around 25 nautical miles or so. We are heading to Shroud Cay – one of my favorite stops!

You have a few options for anchoring – check out the charts. If you have a shallow draft vessel, try North Shroud Cay which puts you very close to Sanctuary Creek.

The Sanctuary Creek dinghy ride is an absolute must for any Exumas visit. The mangrove “river” is full of sea life such as turtles and rays. On other other side is the absolutely stunning Driftwood Beach and Camp Driftwood.

You are permitted to motor at idle-speed. PLEASE NOTE: you need to check the tides and begin this river ride on a mid, rising tide. This will give you time to explore and avoid being stranded. The river is only passable on a mid or high tide.

Beach your dinghy, and enjoy a ride or two on the water slide. Here’s a video of us enjoying it on a recent trip.

Camp Driftwood is worth exploring, so bring some walking shoes. It was built in the 1960s by a hermit who lived there with his sailboat. The camp was later used by the DEA to conduct reconnaissance on the drug kingpin Carlos Lehder’s operation at Norman Cay.

Make sure you don’t get stranded! Head back to your yacht on a flooding tide and enjoy another spectacular Bahamian sunset.

Note: depending on the tides, it may make more sense to ride the river the next morning, on Day 7.

Day 7: Final day optionality

Sail Rocks North anchorage sunset
Enjoying the sunset at the Sail Rocks North anchorage

You have a few options for a final day in the Exumas – each of these is a logical jumping off spot to make the crossing back to Nassau the next day.

Norman’s Cay

The main attraction here is the sunken drug plane from Carlos Lehder’s activities in the 1970s. If you want to snorkel it, try and do so at slack tide.

Macduff’s is a quaint restaurant ashore which seems like it is in the middle or nowhere. You may want to radio ahead for reservations if you plan to eat there for dinner.

Anchoring is easy on the west side of the cay. You can also anchor in the cut closer to the sunken plane – you will swing on the tide, so be prepared.

Construction activity could be from a company that is doing a large-scale development of the island.

Highbourne Cay

Check out the information under Day 2.

Allen’s Cay

This is the location for the local species of iguanas. There are numerous anchorages marked on the charts. Be prepared to share the area with tour boats depending on when you arrive.

Sail Rocks North

This is a settled weather anchorage that we visited on our most recent trip. If you want to get away from the crowds and fish the northern drop, this is the place to be.

Day 8: Crossing back to Palm Cay

Hopefully the wind gods cooperate and give you some great, downwind sailing. The first time we made this crossing back to Nassau, we had 5 knots directly behind us – no fun!

If you weren’t able to have a lunch stop at a coral head, give it a shot.

You may either return to the Palm Cay marina and enjoy the amenities, or, head over to Rose Island if you prefer another night on the hook. Make sure you plan for time in the morning to return and go through check-out procedures – it’s about an hour’s motor.

Sandy Toes is a excursion-focused bar at Rose Island. There are mixed reports of whether they permit cruisers to come ashore.

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Bareboat Charter Key West | Sailing Adventure to the Dry Tortugas

Drone shot of Garden Key and Fort Jefferson at sunset

It had been awhile since I had seen a few friends from growing up in California. We got to talking on a group text, one thing led to another, and soon we were booking a guys sailing vacation trip 10 days from departure!

We looked at a couple nearby destinations, such as Miami, the Bahamas, or the Caribbean. Ultimately, we settled on a Key West bareboat charter with a visit offshore to the Dry Tortugas National Park..

It had everything we were looking for in a short guys trip: close to home, excellent fishing prospects, long days on the water, pre-Civil War era fort exploration, and a bit of nightlife on Duval St in Key West.

Planning and our last-minute booking

This is the first sailing yacht charter trip I’ve booked during hurricane season. After checking the long-range weather models routinely on Tropical Tidbits, it looked like we had a clear weather window – so we went for it. We were careful to avoid the fate of Ernest Hemingway who was marooned at Fort Jefferson for 17 days when a tropical storm moved through!

There are not many options for a bareboat yacht charter to the Dry Tortugas. I found one, but it was not a great option – a Dream Yacht Charter (they have since closed the base) 2018 Bali 4.3 with a flybridge, but no AC!

Yes, I’m spoiled. But this was a guys trip and we decided to rough it even though this was August in south Florida. Better to go and sweat than not go at all.

I picked up a copy of the Waterway Guide Florida Keys to help with our route planning. It was helpful to understand the cruising grounds and key landmarks. Be advised there is not much information about anchorages (since there aren’t that many!). The best resource for that info is Garmin ActiveCaptain.

I wrote more about what to expect in this post.

Boat trouble a-brewing

Stock Island Yacht Club and Marina sunset
Enjoying the morning breeze at the poolside dock at Stock Island Yacht Club & Marina

We arrived early on Wednesday and had a few hours to kill before boarding at 5pm. We got our first taste of the Florida sun as we explored downtown Key West and secured some souvenirs for the kiddos back home.

Garbo’s, made famous by the Diner’s Drive in and Dives, was a welcome respite from the heat. Check out the Umamiburger or Mahi Tacos and pair with a cold beer from the attached Hanks Saloon. The live music was already jamming.

Fish tacos at Garbo's
Cold beer and fish tacos at Garbo's and Hanks Saloon

Check in went smoothly and it was a luxury to have a well-established food delivery program available through Instacart. Prices were high, but it’s much cheaper than you’d pay on a bareboat trip in the Caribbean.

After stowing away our provisions and gear, we moved the catamaran over to the pool dock where we could better take advantage of the prevailing breeze (no shore power AC either since the boat was 220v).

We enjoyed the pool, showers, and restaurant available to charterers at the Stock Island Yacht Club and Marina. They also have a small store a short distance walk from the main building.

Unfortunately, the next morning we learned that an engine water pump was failing and the inverter was busted. We could live with the inverter, but a replacement would be needed for the pump. 

When the pump didn’t arrive on time, we decided to salvage the day and sailed down to the coral reef in Western Sambos for a swim and snorkel. We spent the night at anchor outside of Stock Island to soak in as much breeze as possible.

Sailing to Dry Tortugas - our catamaran finally gets underway

Boca Grande Key Sunset
Epic sunset over Marquesas Keys at Boca Grande

We received a call from DYC the next morning with a new plan – they just had a Nautitech 40 check back in that was available during out trip. After an inspection, cleaning, and swapping out of our gear, we were ready to get west – towards the Dry Tortugas at last! We jammed some sailing tunes and got underway.

Side note: I hadn’t been on a boat type quite like the Nautitech 40 – it has two helm stations at deck level. This made visibility for the helmsman especially difficult. After the challenge of dodging lobster trap buoys throughout the trip, let’s just say I won’t charter a boat like this in the future (unless of course it’s my only option).

Given the late departure, we spent our first night anchored off Boca Grande. The remaining 50 nautical miles to Fort Jefferson at Garden Key we would tackle the next day. You can enjoy spectacular sunsets here over the Marquesas Keys. 

What to expect from the Key West Bareboat Charter cruising grounds

If you choose this anchorage, expect to swing with the changing tide, so make sure you get that anchor set well. This is one of the reasons the Florida Keys or Key West requires more sailing experience and isn’t considered a beginner bareboat charter cruising ground. These are some other reasons – I go into more depth in this separate post about what to expect.

  • Few protected anchorages
  • Mostly anchoring, limited moorings available
  • Longer passages
  • Trickier navigation with shallow areas and hazards to avoid (such as lobster buoys!)
    • Dodging the lobster trap buoys was very frustrating – here’s my advice: charter a boat with good visibility from the helm station and go farther south on your route to the park (time and weather permitting)
    • I asked the operator of the Yankee Freedom (high speed catamaran that takes tourists to the park daily) if there was a better route to avoid the buoys – they confirmed there is no better route than the one we took
  • Less predictable weather – shiftier trade winds, hurricane season, and cold fronts in the winter

Fishing en route to the Dry Tortugas

king mackerel near key west
Little tunny caught near key west florida

Being a guys trip and all, we took the fishing seriously!! We brought our own gear and tackle. Ilander skirt lures were rigged with ballyhoo. Most of the time we fished in 30-60 feet of water, but we also ran south past the reef to deeper water (300+ feet) in search of tuna, mahi, and wahoo.

We trolled with two rods – one with the ballyhoo towards the surface, and the second with a diving artificial lure (Rapala X-rap Magnum for example).

We weren’t able to go too far offshore because of the ground we had to cover, so we had to settle for fish caught in the shallower depths. This time of year when the water is warmer, the pelagic species are generally going to be farther out towards the Gulf Stream – apparently out of reach for us on this trip.

If you want to learn more about how we fish, check out our sailboat fishing guide.

Dry Tortugas sailing route
Our track, with an attempt to reach deeper water on the westward passage | Pins are where we landed fish

Dry Tortugas fishing totals – I give us a C+

It was a decent haul, but we didn’t do as well as expected. Sadly, nothing was caught that we wanted to make fish tacos out of. Here are the totals for the trip.

  • 3 barracuda (one of which was the biggest I’ve ever caught…and I seem to catch a lot of them)
  • 2 king mackerels 
  • 1 little tunny

If you do fish, be aware of the the fishing regulations for the Dry Tortugas National Park – certain areas are restricted and you should stow your gear before arriving. If you do have any fish aboard, radio the Park Rangers on Channel 16 to report your catch before entering the park boundaries.

Within a mile of the Garden Key, fishing is permitted from a boat.

Exploring Fort Jefferson and Garden Key

Exploring Fort Jefferson
Exploring Fort Jefferson after the crowds from the Yankee Freedom had left | We had the place to ourselves

Adventure was the objective for this trip, and what could answer more than a long journey to the least visited lower 48 National Park with plenty of history?

We arrived at the Garden Key anchorage and found that we had the it all to ourselves (one boat later arrived)! Excellent. The crowds from the daily Yankee Freedom ferry were also gone so the fort was empty.

Before going ashore, I dove on the anchor and was visited by the largest barracuda I’ve ever seen. I’m sure he makes the anchorage his home – he hung around under the boat during our entire visit. I was also hoping to see some of the goliath groupers during the day, but they only showed up after dark.

Fort Jefferson at the Dry Tortugas National Park

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Heading ashore at Dingy Beach

We took the dingy in at, yes, Dingy Beach (there is a sign, you can’t miss it), and walked over to the boat pier to get our permit – it’s free. All you need to do is pay your entrance fee ($15/per person). The office also posts daily weather reports for the boating community.

Following the self-guided tour, we enjoyed learning about Fort Jefferson such as the construction, purpose, and famous prisoners including Dr. Mudd. Atop the fort next to a monster Parrot Rifle, it was fun to see our catamaran lying peacefully in the anchorage below.

You can also camp at the fort – and we spent some time mingling with a few of the campers. Most had taken fishing boats to the fort, enjoying the bountiful waters surrounding the National Park. We were jealous of their fresh catches!

Unfortunately, the very next day we had to begin the return trip to Key West since we lost a day with the boat issues. Next time we return, we’ll make sure we have more time for adventuring and exploration in the park, including Loggerhead Key.

Homeward bound - back to civilization

Dodging squalls on the way to the Dry Tortugas on a bareboat charter trip
Dodging isolated squalls on our return to Key West

With the prevailing trades blowing in our teeth and a long distance to cover, we had to motor much of the way back. Such is the reality of a catamaran charter trip with firm travel dates.

We spent another night at Boca Grande with a mesmerizing sunset, one of the most magical I’ve seen. There was a massive thunderstorm complex to our north that put on quite the lightning show for hours and hours. 

We thought it was coming closer at times, but thankfully it stayed away. This made the perfect backdrop for a showing of Master and Commander, which we enjoyed with our projector after sunset cocktails. 

I slept on the catamaran trampoline out front each night, and this was the only time I was scared away below decks due to the approaching storms!

Our last day and a change in plans

On our way back to the marina, we enjoyed some more fishing and snorkeling at Western Dry Rocks. Check the state park and fishing regulations, but fishing and lobstering was permitted at this location during our visit. Unfortunately, I came up empty handed on the spiny lobster this time.

After swinging by the fuel dock in the afternoon at the Stock Island Yacht Club and Marina, we decided to debark and find a hotel. Our flights didn’t leave until the next evening, so it allowed us a refuge to hang out for the next 24 hours.

We chose the Perry Hotel, a welcome respite from the heat at neighboring Stock Island Marina. We enjoyed showers, a poolside happy hour, and of course – some AC! It was the perfect place to wind down and share sea stories from our Key West sailing charter trip.

Poolside happy hour at the Perry Hotel
Poolside happy hour at the Perry Hotel

Not qualified to do a Key West bareboat charter on your own yet?

Check out our starter guide here if it’s something you are interested in. 

Can you still take a similar trip in Key West? Yes! Crewed charters are available. Ask your charter company and they can help pair you with a skipper for the Florida Keys. You can also look into a power catamaran option if you have some boat know-how.

You may also stay in Key West and take some day trips. Day charters aboard catamarans are available for reef snorkeling and sunset cruises. The high-speed ferry Yankee Freedom also leaves Key West daily at 8:00am to bring you to the Dry Tortugas. You’ll be back by 5:00pm.

Thanks for reading my post about a Key West bareboat charter to the Dry Tortugas! If you enjoyed it, please subscribe or check out some of my other articles, like this one about sailing to St Croix and visiting the Spanish Virgin Islands.