Types of Yacht Charters: 4 Ways to go Sailing

Pirate's Lair in the Exuma Bahamas on a Exuma Yacht Charter

Are you searching for the best vacation ever? Look no further than a yacht charter trip with family and friends. Yacht charters allow you to discover beautiful destinations around the world in style, while enjoying the freedom and flexibility of your own yacht.

As tourist destinations become busier and busier, there is no better way to escape from it all and find your own private paradise. Leave the crowds behind and explore remote and secluded islands that are only accessible by boat.

While I spend most of my time on bareboat charters, there are three other types of yacht charters. Something for everyone and every type of budget! In addition to bareboat charters, you can go sailing on a crewed yacht charter, bareboat with a hired skipper, or as part of a by-the-cabin trip.

Each yacht charter type has its pros/cons, but it ultimately comes down to your budget, type of crew, and sailing experience level.

Let’s take a closer look at each type of yacht charter to help you plan your next sailing adventure.

crewed yacht charter cockpit
Expect to be pampered aboard a crewed yacht charter | This is the cockpit of Chaos Interrupted

Fully crewed yacht charters: the luxury, all-inclusive option

Image above: Chaos Interrupted a top-rated crewed yacht charter available in the Virgin Islands.

Crewed yacht charters are sometimes considered the all-inclusive option and range from 45 foot catamarans all the way up to large mega yachts.

For sailing catamarans, you can expect it to be crewed by a captain and a hostess. As a team they will work together to take care of all your needs while you sit back and relax. They will:

  • Handle all of the yacht maneuvers, anchoring, and sailing

  • Provision for food and drinks

  • Cook you spectacular meals (and clean-up!)

  • Mix you up your favorite island cocktail

  • Provide water sport activities such as stand up paddleboards

  • Take you to secret snorkel spots

  • Drop you off on the beach for some bar-hopping

  • Help you catch a mahi

  • …and more!

You book for the crew just as much as you book for the yacht – the right crew can offer an unforgettable experience.

This is the ultimate, luxury option. As such, expect to pay up for a crewed yacht charter. Depending on the type, size, and age of the sailing catamaran, this can range anywhere from $15,000 to $50,000+ (before tip).

For families with small children, this might be the best option so you can focus on keeping a watchful eye on the kiddos, especially when the boat is moving.

To book crewed yacht charters, you typically must work directly with an independent yacht broker, such as the Yacht Warriors.

The Baths in the BVIs on a bareboat charter
The Baths in the BVIs, the most popular crewed yacht charter destination

Where to go on a crewed yacht charter?

The largest fleet of crewed sailing catamarans in the Caribbean is in the British Virgin Islands and USVIs. Antigua is also another popular Caribbean destination for crewed charters. You can also find a handful of options in the Bahamas (technically not the Caribbean, but close enough!).

Globally, you have plenty of options such as French Polynesia, the Mediterranean (Croatia, Greece), and Hawaii.

Why you might like a crewed yacht charter

  • Enjoy a stress-free vacation with a professional crew taking care of all the details

  • Access to included amenities and services such as gourmet meals and water sports activities

  • You don’t want to do any of the cooking or clean-up

  • Customize your itinerary, with unique insights from the knowledge of your captain and host

  • Experience spacious cabins and common areas, and top-quality furnishings

  • You are celebrating a special occasion or don’t yet have the experience to take out your own sailing yacht

Sail Rocks North anchorage
North Sail Rocks in the Exuma Bahamas - not another boat in sight

Bareboat charters: the freedom to explore all on your own

On a bareboat charter you serve as the captain, supply the crew, make provisioning arrangements, and decide where you want to go. A bareboat charter simply means that you rent a boat from a charter company for a defined period of time. The charter company will qualify your sailing experience to make sure you have a safe and fun trip.

Read more about what it takes to become qualified and go on your first bareboat charter.

On your bareboat charter, you have the freedom to do whatever you’d like (within reason or course) during your trip – sailing, snorkeling, fishing, beach bar hopping etc.

Bareboat charter pricing can range anywhere from $5,000 for a smaller monohull all the way up to $20,000 for a larger sailing catamaran. Learn more about how they are priced in this post.

Epic sunset at Magen's Bay, St Thomas, USVI
Magens Bay in the US Virgin Islands, another popular bareboat charter destination

Where to go on a bareboat charter?

Whereas with a crewed yacht charter, you are restricted to destinations with a crewed charter industry, on a bareboat charter you have much more flexibility on where to sail. These are a few of my favorite Caribbean bareboat charter destinations.

The British Virgin Islands remains the best place for beginners: idyllic Caribbean surroundings, settled weather conditions, easy navigation, and plenty of mooring balls are a few reasons to start there.

Other places to go? Check-out Belize, the Grenadines, French Polynesia, the Mediterranean, Thailand, or Key West.

Why you might like a bareboat charter

Bareboat chartering is my favorite way to vacation for several reasons. Here are a few of them:

  • We enjoy the privacy of sailing without a skipper or hostess

  • Our crew doesn’t mind cooking or cleaning

  • It’s more affordable as the DIY option!

  • We enjoy developing new sailing skills and building confidence from getting out there and doing it

  • You can explore previously off-limits destinations, and venture farther as you build more experience

Bali 5.4 in the Exumas on a bareboat charter trip
Discover sailing vacations by hiring a professional skipper

Bareboat with a hired skipper: sailing with a professional

This option is similar – you book a bareboat charter from a charter company, but you add a skipper option. This usually costs $200-300/day in addition to the rest of your bareboat charter pricing.

In addition, you’ll need to save a cabin for them and provide food for them during the trip. Another variation is to also add a hostess option, in a similar fashion.

Well that sounds like a crewed charter option, right? Well sort of, but not really. You don’t know exactly who you getting as a skipper/hostess (usually not a team that works together), and you still pay for provisions and extras such as water sports.

Boca Grande Key Sunset
The Florida Keys are a popular destination to hire a skipper due to the stricter qualifications required | Anchored at Boca Grande Key

Where to go on a bareboat charter with a skipper?

You can charter in most bareboat charter destinations with an added skipper. In some destinations, such as Florida, you are required to contract directly with the captain, but they can provide a list of recommendations for you. These are my favorite destinations to charter.

Why you might like a bareboat charter with skipper option?

  • You don’t mind handling the cooking/cleaning, but you don’t yet have the experience to sail

  • It’s a good way to see if bareboat charter trips are for you and the crew – test those waters out

  • If you have some sailing experience, you’ll get to practice hands-on with a professional captain

Shroud Cay Exumas
The Exumas regularly have by-the-cabin charters available | On a mooring ball at Shroud Cay

By-the-cabin charters: a more affordable way to sail

By the cabin yacht charters are a great option for those who want to experience the luxury of a fully crewed charter, but don’t have the budget for a private yacht.

With this type of yacht charter, you’ll book a cabin on a larger vessel, which will be shared with other guests (some of which you might not know). You’ll still have access to a skipper/hostess and all the amenities of a private yacht but at a fraction of the cost.

This is also a good option if it’s just the two of you and you’d like to be social and meet some new travelers during your trip.

North Sound in BVI, another popular by-the-cabin destinationm

Where to go on a by-the-cabin charter?

Your options here are probably the most limited of all four types of yacht charters. You also have to be flexible on your travel dates, as these trips are scheduled well in advance.

I’ve found your best options for by-the-cabin charter charters are first, the BVIs, and second the Exuma, Bahamas.

Why you might like a by-the-cabin charter?

  • Enjoy the luxury and comfort of a fully crewed yacht, at a fraction of the cost of a private charter

  • Meet new people and make new friends, as you share the vessel with other like-minded travelers

  • Benefit from the expertise and local knowledge of a professional crew

That’s it! Whether you prefer the all-inclusive crewed yacht charter or the freedom to explore on your own bareboat charter, there a type of yacht charter for everyone. If you have any questions about going on a sailing trip, please reach out by web chat, phone, or email!

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

BVI bareboat charter

Photo: anchored in front of the Soggy Dollar Bar at White Bay, Jost Van Dyke on one of our recent trips.

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


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


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).


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.


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 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.

Request a Yacht Charter Quote

We have relationships with all of the 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.
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.


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.


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)?

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! 


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? 


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 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.
North Sound in Virgin Gorda, BVI

First time BVI bareboat charter sailing itinerary

We’ve visited the BVIs five 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).

Check out my most recent story about our BVI bareboat charter here. 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.
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.
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.
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.

Top 10 Bareboat Charter Travel Hacks

If you do it right, bareboat yacht charter trips are the most enjoyable vacation you can take.

But, many crews take years to learn simple tricks to make things more fun and less stressful.

We’re now on our 10th year of chartering, so, here are our top 10 bareboat charter hacks that you should know.

Wahoo caught on the drop in the Exumas sound
Catching wahoo on the drop in the Exumas

Bring your own fishing gear

We didn’t fish on our first couple yacht charter trips, but this is now one of the activities we most look forward to.

Trolling while sailing (or motoring) adds a layer of excitement – you never know when those reel alarms are going sound off, and when they do, what might be on the other end of the line.

Yes, we catch a lot of barracuda, but we now also catch mahi, tuna, and wahoo to cook up right on the catamaran.

I’ve rented gear in the past, but I’d recommend making the investment in some high-quality gear that will last you for years. Read more about why and what those recommendations are in my sailboat fishing guide.

Watching Master and Commander afloat
Watching Master and Commander on a recent yacht charter trip

Project a sailing-themed movie

Yes, I know we are trying to unplug and get away from it all…but, tell me it’s not fun to throw a movie like Master and Commander or Pirates of the Caribbean up on the big screen (sheet!).

It’s awesome!

We pack a projector, some duct tape, and a white sheet – that’s all you need.

We only do it once or twice on a trip. It’s a fun way to mix things up for a chill night on the boat in a secluded anchorage. If you’re travelling with kids, definitely add this one to the list.

Pack your own first aid kit

Don’t expect much out of the boat-supplied first aid kit, and you don’t want to be empty handed. Sunburns, snorkel scrapes, and cuts (watch out for those glass bottles in the trash). It’s a boat trip after all.

In addition to some better antiseptic and water-resistant band aids, we stock a mini pharmacy to provide relief for the usual suspects: tummy trouble, seasickness, nausea, hangovers, etc.

It’s also helpful to be prepared for other types of illnesses such as food poisoning or the every day cold. It might be a day or two before you can reach a store to pick up some meds.

Flying the colors, including the Florence Marine X burgee
Bring whatever flag floats your boat

Fly your favorite flags

Don’t be shy – make sure all the other cruisers know where your allegiances lie! Sports teams and colleges are popular, or you could have your own crew’s private signal designed/produced.

One year we even flew the House Stark flag from Game of Thrones since we were chartering during the final season.

Anything goes!

Bigger flags are best flown off the topping lift, whereas you can fly burgees from the spreaders. There is plenty of sailboat flag flying etiquette, but we tend to be pretty liberal in our approach.

Lounging on the Bali 5.4 flybridge
The flybridge on the Bali 5.4 is huge!

Go with the flybridge option

If you are chartering a catamaran, I can’t stress enough how much better a model with the flybridge can be.

What’s a flybridge? A lounge or hang out area beneath the boom on (usually) bigger catamaran models – ~45+ feet.

Sometimes it’s also tied in with the helm station. We love those models since it allows everyone to hang out up top together. When we’re sailing, that’s where everyone collects.

If it’s not a flybridge, usually there is a lower helm station with room for 2 people. I think that’s a fine option for a crewed charter, but when we are all doing the sailing, it’s way more fun to be on a flybridge, together.

Learn some basic maintenance

Even the best-maintained boats sometimes have issues. We expect it to happen on any bareboat charter trip, we just hope they are minor.

If we do encounter a problem, we would prefer to not sit around and wait for a chase boat from the charter company.

Some common issues we have troubleshooted in the past:

  • Dinghy outboard won’t start

  • Clogged impeller from sargassum

  • Prop wrap

  • AC or water maker not working

Make sure you check first – some companies want to be notified before you attempt even minor fixes. They can also help you talk through simple solutions, such as switching a breaker.

We also perform some preventative maintenance tasks as recommend by the charter companies, such as daily engine checks – oil, coolant, belts, etc.

Vacuum sealing some meats ahead of one of our trips

Bring some frozen, prepared meals with you

We eat the majority of our meals on the boat, and while I love cooking, I would rather be enjoying the sunset with a cold beer.

To minimize time spent in the galley, we recently started bringing some frozen or prepared meals with us. I’m a big fan.

Not only does it save you some time, but you can usually purchase higher quality food items near your home. Simply cook up the food, food wrap it, and pack it in a carry on or cooler backpack. It will stay mostly frozen even after a full day of travel.

Here’s what we brought with us on a recent trip.

  • Frozen taquitos

  • Some high-quality filets – to celebrate the first night of the trip

  • Grilled chicken thighs – to go with rice/broccoli

  • Frozen Costco meatballs – for pasta night

  • Lunch meats

Fishing route in Vieques
Tracking our fish hook-ups on a Spanish Virgin Islands trip around Vieques

Start using the Boating App

Navionics’ Boating App for your phone or tablet is one of the best planning tools for your charter trips. Plan your routes and check out the Active Captain community features to learn more about new anchorages.

We also use it during the trips as a back up to the chart plotter. I’ve had one fail in the past.

Another way it’s great? Layers such as Sonar Chart and Relief Shading help us to stay on bottom structure or one of the drops when we’re trolling.

A subscription is only $30.

80s Night in Cruz Bay USVI
80s night in Cruz Bay, St. John

Dress up for an evening ashore

What’s more fun than organizing a theme and heading ashore for a night on the town (or beach bar)? We recently did this with an 80s night in the USVIs and it was a highlight of the trip.

I promise you that you’ll make some awesome memories and come away with great photos.

Other theme ideas? Pirate, white-out, gala, or luau are always fun concepts for a yacht charter trip.

Stand up paddleboarding in the Exumas
Paddle boarding in the Exumas

Skip the kayak option

We added a kayak option once, and it was a one and done. I enjoy cruising around in a kayak, but they are heavy, awkward, and a pain to stow back on deck.

So much so that we stopped using it.

For water sports, go with the stand up paddle board instead – they are much lighter and easier to handle.

Worried about being able to use one? It is perfectly acceptable (and more stable) to paddle from your knees.