Should you charter the Spanish Virgin Islands from Puerto Rico or USVI?

Culebra sunset at Carlos Rosario beach

Embarking on a sailing adventure in the Spanish Virgin Islands (SVIs) is like uncovering a hidden treasure of the Caribbean. These islands offer a blend of solitude, pristine beauty, and a sense of discovery reminiscent of the British Virgin Islands two decades ago.

When planning your yacht charter to the SVIs, a key decision is choosing your starting point: Puerto Rico or the U.S. Virgin Islands (USVI). Both locations offer unique advantages for sailors, and I’ve had the pleasure of setting sail from both. Here’s my perspective on each:

Puerto del Rey, one of the largest, most protected marinas in the Caribbean | Source: Puerto del Rey

Puerto Rico, Puerto del Rey:

  • Ease of Access: With plenty of direct flights from the U.S., getting here is hassle-free.
  • Sailing Conditions: The route offers more protected sailing. Starting counterclockwise with Culebra gives you some lee protection, while the route around Vieques typically has the prevailing wind and current in your favor.
  • Provisioning: Good options are available, but it’s more of a do-it-yourself situation, with no delivery services that I know of.
  • Charter Options: The fleet might is smaller just several catamarans and monohulls
  • Travel Time: It’s a bit of a trek from the airport to Puerto del Rey marina, taking about 45 minutes or more.
Frenchtown Marina in St Thomas, where the Waypoints charter base is located as we prepare for our yacht charter sleep aboard
Frenchtown Marina - just a quick 15 minutes from the airport

U.S. Virgin Islands (USVI):

  • Convenience: In St. Thomas, you can be on your catamaran within 15 minutes of leaving the airport – believe me, I’ve done it!
  • Sailing Route: Expect an easy downwind passage to Culebra. The upwind return to St. Thomas can be challenging, but with luck, you might catch favorable winds, as I did on one trip.
  • Customs: Clearing customs in Culebra is a breeze, especially using the CBP ROAM app, and there’s no need to disembark.
  • Provisioning: St. Thomas offers excellent options with delivery services right to your catamaran.

Read about my last trip where I chartered to the Spanish Virgin Islands from St. Thomas, USVI.

The SVIs: A Sailing Haven

The Spanish Virgin Islands have a fascinating history, including military training activities, which is part of why tourism here isn’t as developed as in the neighboring Virgin Islands. Despite this, the SVIs offer a sailing experience that’s hard to beat, with untouched beaches, solitude, and superb fishing. You can learn more in this post about sailing in the virgin islands. 

Sailing Map

Suggested Itinerary: Opt for a Clockwise Route

Whether you start from Puerto Rico or the USVI, a clockwise itinerary is optimal. Beginning with Culebra, you sail east with some protection from the island’s lee. As you head towards Vieques, you’ll often find yourself sailing downwind, making for a smoother ride.

If starting from the USVI, simply check in at Dewey and continue your clockwise adventure. Either way, a remarkable journey awaits.

Learn more about my recommended Spanish Virgin Islands sailing itinerary.

Tank at Flamenco Beach
Playa Flamenco in Culebra, a global top 10 beach

Final Thoughts

A yacht charter in the Spanish Virgin Islands promises an unforgettable experience, whether you choose Puerto Rico or the USVI as your starting point. Both offer unique advantages, but regardless of your choice, you’re in for a journey filled with natural beauty, tranquility, and adventure. Set your sails and let the trade winds guide you through these hidden gems of the Caribbean.

How much does it cost to charter a catamaran in the Caribbean?

Catamarans lined up in front of the Soggy Dollar Bar in White Bay, Jost Van Dyke, BVI

One of the most frequently asked questions by charterers and vacationers alike is: “How much does it cost to charter a catamaran in the Caribbean?” The answer largely hinges on the type of charter you opt for. The cost to charter a catamaran in the Caribbean ranges from just a couple hundred dollars to $50,000+. That’s a pretty wide spread!

Most commonly, a week-long bareboat charter on a catamaran for a crew of 8 will cost between $7,500 and $15,000.

Let’s break it down.

Sunset at the Bight, Norman Island in the British Virgin Islands.

Fully Crewed Catamaran Charters

This luxury, all-inclusive option offers a crew comprising both a captain and hostess to manage all your needs — from tantalizing meals and drinks to guided island adventures. For such charters in the Caribbean, prices can vary from $15,000 to a staggering $50,000+ before gratuities.

charter catamaran in the Exuma Bahamas
Sailing the Exumas on our Bali 5.4 bareboat catamaran

Bareboat Catamaran Charters

If you have the required sailing expertise, you can captain your own adventure. With this, you’ll be in charge of provisions, itinerary, and more. Caribbean prices for these catamaran charters start at around $6,500 and can soar up to $20,000+ for more luxurious and spacious options, especially in the high season.

Catamaran anchored at sunset in the Bight at Norman Island, BVI
Hired skippers are available in almost every charter destination

Bareboat Catamaran with a Hired Skipper 

This is akin to a bareboat charter, but with the added peace of mind of a professional skipper. In the Caribbean, expect to add an extra $200-300/day to your charter cost. And don’t forget to set aside a cabin and provisions for them. It is also customary to budget for a 20% tip for excellent service.

Pirate's Lair in the Exuma Bahamas on a Exuma Yacht Charter
The Exumas is a popular destination for by-the-cabin charters

By-The-Cabin Catamaran Charters

Perfect for those who yearn for the opulence of a crewed charter but have a more restrained budget. Here, you book a cabin on a larger catamaran shared with other travelers. This option offers many of the luxuries of a private yacht but at a fraction of the cost. Prices can vary widely, but for a ballpark estimate, think in terms of several hundred to a couple of thousand dollars per cabin, depending on the amenities and duration.

For those with their sights set on the Caribbean, the British Virgin Islands (BVI) stand out as a premier destination for both crewed and bareboat catamaran charters. Moreover, the Exumas in the Bahamas offers another enticing choice, especially for by-the-cabin charters.

New to yacht chartering? Learn more about the four different types of yacht charters.

So when pondering: How much does it cost to charter a catamaran in the Caribbean?, it’s evident there’s a spectrum of choices catering to varied budgets and preferences, ensuring a Caribbean sailing experience that’s just right for you!

Considering a catamaran charter in the Caribbean? The Yacht Warriors can get you pricing today. Learn more.

Sailing the Virgin Islands: What We’ve Learned

Setting Point Anegada

When you think about sailing the Virgin Islands, the British Virgin Islands certainly come to mind, and perhaps the US Virgin Islands. But did you know about the third part of the VIs, the Spanish Virgin Islands?

We’ve sailed in all three, multiple times, and it’s our favorite place to charter.

If you’re planning to sail the Virgin Islands, find out what I’ve learned about cruising conditions, when to visit, and what to expect at each of the three very unique sisters of the Virgin Islands.

The Baths, BVI
A typical day in the British Virgin Islands with puffy tradewind cumulus clouds

Cruising Conditions in the Virgin Islands

You’ll enjoy some of the best yacht charter sailing conditions anywhere thanks to the steady easterly tradewinds and the protection in the lee of the islands from waves and swells.

Generally, for weather conditions, you can expect steady 10-15 knot trade winds from the ENE-ESE, puffy tradewind cumulus clouds, and an occasional shower or squall.

In the winter months, you can expect Christmas Winds to blow occasionally: several days of strong winds (15-30 knots) created by high pressure systems in the Atlantic. This is also considered the dry season.

On the other hand, the summer months are wetter due to passing tropical waves or disturbances. In between, winds tend to be lighter.

example of backwinding while anchored
An example of how backwinding works while we are anchored at Muskmelon Bay

Virgin Islands weather features

Navigation is mostly line of sight with the exception of certain areas, such as Anegada. There are few navigational hazards compared to a destination such as the Bahamas.

Tides are not significant, and you can expect a 0.5 to 1.0 knot current that moves from east to west.

Northerly ground swells can catch novices off guard. They affect northerly exposed anchorages, making them uncomfortable and potentially dangerous from mainly Nov – Apr. You can read more about them in this post about BVI weather resources.

Backwinding is possible at some Virgin Islands anchorages if strong winds are blowing (15+ knots) over steep, tall terrain.

View of Culebrita, one of the Culebra anchorages
Perfect day at Culebrita in the Spanish Virgin Islands

Best time to go Sailing in the Virgin Islands

If you’re planning to go sailing in the Virgin Islands, you should consider the four different sailing seasons:

  • High season: December to March

  • Shoulder season one: April to June

  • Peak hurricane season: July to October

  • Should season two: November

Personally, my favorite time to visit is during shoulder season one. We enjoy predictable weather, longer days, steady wind speeds, fewer crowds, and cheaper charter prices.

white bay east side jost van dyke
Expect crowded mooring fields in the BVI during high season

High season: December to March

This is the busiest and most expensive time of the year in the British Virgin Islands and US Virgin Islands. The Spanish Virgin Islands are always going to be a bit sleepier. Hurricane season is over, and the annual pilgrimage of cruising boats has made it’s way from mainland U.S. and Europe to enjoy the warm Caribbean winter.

Expect crowded mooring fields, shorter days (almost 2 hours shorter than the summer), and a visit from the Christmas Winds.

Shoulder season 1: April to June

This is my favorite and I believe the best time to visit the Virgin Islands for sailing trips. We’ve been to the VIs 4x in May. The crowds have thinned out somewhat and the weather has become more settled.

Expect easy 10-15 knots from the E to SE and an occasional shower to cool things off.

Our catamaran at anchor at Playa Flamenco
Playa Flamenco in the Spanish Virgin Islands during a passing tropical wave

Peak hurricane season: July to October

Many charter companies put their boats on the hard for hurricane season, but it’s still possible to book. Expect great deals, and you might have the whole anchorage to yourself.

Just keep an eye on the tropics – try these strategies for chartering during hurricane season.

Shoulder season 2: November

This is my second favorite time to sail in the Caribbean.

Again, the crowds haven’t arrived yet and the weather tends to be settled – similar to April-June. Some tropical mischief is still possible, but you’ll see lower prices than December.

Sunset at the Setting Point - Anegada
Setting Point in Anegada on our 2023 trip

The three sisters of the Virgin Islands

British Virgin Islands

The British Virgin Islands is the global yacht charter capital, for good reason.

Not only is the BVIs the best place for first-timers, but you’ll find yourself returning year after year. There’s something about it that keeps drawing you back.

I’ve spoken with some old salts that have made over 30 trips!

It’s popularity owes itself to the unique geography, with many islands and bays to explore, sheltered from the trade wind driven swells.

What makes it so great?

  • 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 – the BVIs have few major navigational hazards (if you pay attention to red-lined areas) and the sailing is usually line of sight

  • Amenities – there are bars and restaurants to fill your heart’s desire

  • Mooring balls – plenty of well maintained balls are available, making it easier and less stressful for crews

  • Well established bareboat yacht charter industry – lots of operators, a deep bareboat charter fleet, and many services to help make your trip easy

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma) on a bvi catamaran charter
Beautiful evening in North Sound on our first ever charter

Highlights of sailing the British Virgin Islands

  • Hike through the gigantic granite boulders at the Baths to Devils Bay

  • Anchor in North Sound and enjoy the sights of one of the finest harbors in the Caribbean

  • Sail offshore to the sunken island, Anegada. Sip cold beverages at rustic beach bars on the beautiful north shore

  • Go Beach Bar hopping for painkillers at famous White Bay, Jost van Dyke

  • Jump into the water from the second deck of the floating pirate ship bar, Willy-T

  • Discover abundant marine life at the many snorkeling sites, such as the Indians and the Treasure Island Caves

Epic sunset at Magen's Bay, St Thomas, USVI
Magens Bay in St. Thomas is spectacular

US Virgin Islands

The US Virgin Islands don’t get as much attention as their more popular sister next door, the BVIs, but they should for charter crews.

I visited the BVIs four times before exploring a USVI yacht charter. Verdict? I was especially blown away by the Virgin Islands National Park and the beauty of some of the bays.

And, don’t tell the British Virgin Islands, but I think the USVIs have better beaches! (yes I love Anegada’s north shore, but these USVI beaches are more numerous and can be accessed right from your dinghy)

Why might you like a USVI yacht charter?

  • Idyllic Caribbean surroundings – Plenty of protected anchorages. Coconut palm lined white sandy beaches. Great snorkeling and fishing. 

  • 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 some hazards to avoid, but most of the sailing and navigating is point and shoot, line of sight passages

  • Amenities – there are some really fun beach bars and restaurants to visit. There are even vendors you can visit in the National Park

  • Mooring balls – plenty of well maintained balls are available from the National Park Service, making it easier and less stressful for crews

  • Easy logistics – no need for a transfer with many direct flights available from mainland US. You can be on your charter yacht within 30 minutes of landing, seriously!

  • Good for kids -when I take my little kids on a yacht charter for the first time, I think the US Virgin Islands will be the destination. Why? Short passages, plenty of activities, protected swimming/snorkeling areas, and lots of beaches to relax on.

Beautiful fall day at the Maho Bay mooring field on our US Virgin Islands bareboat charter trip
You can't miss the amazing beaches of the Virgin Islands National Park - this one at Maho Bay

Highlights of a US Virgin Islands yacht charter

  • Beach, snorkel, repeat. The Virgin Islands National Park has countless opportunities for snorkeling and beaching all day long. The setting doesn’t get any better thanks to its protected status.

    • Hawksnest Bay for turtle sightings

    • Trunk Bay for the underwater snorkel trail

    • Cinnamon Bay for swimming and gazing at luxurious villas

    • Maho Bay for the awesome beach

    • Leinster Bay / Watermelon Cay for the best snorkeling in the Virgin Islands

  • Cruz Bay and Coral Bay on St. John are fun, quirky towns with lots of shopping, dining, and drinking

  • The south drop is just an hour away where you have great chances of catching mahi, wahoo, and tuna to cook up right on your yacht

  • Marvel at Magens Bay, one of the most spectacular settings I’ve visited in the Virgin Islands

  • Lime away the afternoon and enjoy an epic unobstructed sunset at Honeymoon Beach, Water Island

  • Grab a pizza from the floating pizza boat, Pizza PI VI, at Christmas Cove

Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage
You'll often find solitude in the Spanish Virgin Islands - this was on our 2022 guys fishing trip

Spanish Virgin Islands

If you haven’t yet sailed the Spanish Virgin Islands on a yacht charter, you are missing out!

Even though the islands are a couple hours sail from St. Thomas, they still feel largely undiscovered. Solitude, beautiful beaches, and excellent fishing are just some of the highlights that rank highly on 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!

You’ll see evidence on your trip of how the US Navy and Marines used these islands for training: target practice tanks on Flamenco Beach and bays that are off limits to anchoring due to potential unexploded ordnance. This is one of the primary reasons tourism here lags its Virgin Islands’ neighbors to the east.

The Spanish Virgin Islands are actually part of Puerto Rico, and it’s easy to coordinate a yacht charter from either the US Virgin Islands or the Puerto Rico mainland. I’ve chartered from both, and I actually prefer from the US Virgin Islands since there is a deeper charter fleet.

The cruising grounds consist primarily of the islands of Culebra and Vieques with several other small islands/cayos mixed in for exploration. If you don’t have a full week to explore, I would spend more time on Culebra.

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. 

Don’t expect beach bars at every anchorage. This is a place to get away from it all and soak in the natural surroundings.

Green Beach, Vieques with a sunset over Puerto Rico in 2020

Highlights of sailing the Spanish Virgin Islands

  • Anchor at picture perfect Tortuga Beach and hike to the lighthouse atop Culebrita for commanding views of the surrounding islands

  • Drop the hook or hike to Flamenco Beach, a global top 10 ranked beach; enjoy $2 Medalla beers from the kiosk vendors and take your picture with the rusting tanks

  • Snorkel the gorgeous reefs on the west side of Culebra right from your yacht, such as at Carlos Rosario

  • Troll fishing lines on the southern drop at Vieques and catch tuna, wahoo, and mahi

  • Book a kayak tour to experience the bioluminescence of Mosquito Bay

  • Experience epic sunsets over the Puerto Rico mainland at Green Beach

  • Take in the local party scene at Isla Palominos on your last night

Hope that was helpful to learn about sailing the Virgin Islands. Check out my Bareboat Charter Guide if it’s your first visit to the British Virgin Islands.

Navigating the Great 2023 Caribbean Sargassum Bloom

The great 2023 Caribbean sargassum blooom

Photo: Flamenco Beach, Culebra in November 2022

By now you’ve surely heard the media reports…it’s coming.

It’s stinky, unsightly, and it’s on the way to ruin your Caribbean vacation.

Yes – this year’s 2023 Caribbean sargassum bloom in the looks like it will be one for the record books, surpassing many other recent seasons.

There are already reports of many popular vacation destinations such as the British Virgin Islands, Bahamas, and Florida Keys, experiencing waves of the stuff washing up on beaches since the beginning of the year.

But don’t cancel your plans. I’m going to show you how to have a great time in the Caribbean this year, in spite of the sargassum. This article focuses on those taking yacht charter trips, but there are useful tips for any type of vacation traveler.

The 2023 Caribbean sargassum bloom - this probably wasn't what you were expecting for your vacation!
This probably wasn't what you had in mind for your Caribbean vacation!

What is sargassum and the why is this year so bad?

Sargassum is a yellowish brown floating seaweed that blooms in a five thousand mile long belt in the Atlantic Ocean, dubbed the Sargasso Sea. It floats on the weather in a westerly direction towards Florida, the Caribbean, Mexico, and Central America.

I’ve been sailing on bareboat charter trips for over 10 years in the Caribbean, and we regularly sail past sargassum patches, or step over it on beaches.

It’s usually not too big of a deal, but some years are worse than others. This looks like one of those.

Scientists believe elevated nutrient levels from rivers and storm runoff are acting like fertilizer for the sargassum, boosting their growth. Manmade causes are usually to blame, but there is still a lot of uncertainty. You can read about its origins in one of the recent media articles on the topic.

The bottom line: batten down the hatches. It’s coming.

2023 Caribbean Sargassum | Source: USF
Sargassum patches detected by satellite imagery, courtesy of the University of South Florida (March 2023)
Caribbean sargassum - April 2023
April 2023

So much is coming that it can be detected by satellite images. The University of South Florida has a great project called the Sargassum Watch Project where you can keep track of the blobs progress. You can even animate the images to see how it’s changing over time.

Here’s how to see the latest sargassum map:

  • Open the webpage and click “SaWS Clickable Map”
  • Select the region
  • Choose the date, there is usually a 1-2 day delay
  • Click “Composite DOY 080”, and then click “FA_UNET_DENSITY 7 Day Information”

Try “Animate” to see how the sargassum is progressing over time.

While this is helpful to identify larger trends, there’s no way to know for sure if your favorite beach will be impacted weeks, or even days in advance.

Sargassum bloom headed to the Caribbean in April 2023
Plenty more sargassum headed to the Caribbean (April 2023)
Sargassum is heavy on the west side of Flamenco Beach in the Spanish Virgin Islands
While the Sargassum was heavy on the west side of Flamenco, Culebra, we had clear near where we anchored on the east side

Navigating Sargassum during your yacht charter trip

Let’s not let the sargassum ruin all the fun. I’ll be sailing in Antigua in May, and while I’m not worried, we are getting prepared to deal with it. Here’s what we are doing.

Keep looking – the sargassum-free beach is out there

The beaches that are most exposed will be windward/eastward facing, as that is the direction the sargassum is creeping from on wind, wave, and current.

Best advice to finding an idlyllic Caribbean beach, sargassum-free? Remain flexible. We’ve always found that even if some beaches are infested, others are perfectly fine.

One example? We visited the beautiful, crescent-shaped Flamenco Beach in Culebra this past November. While the west side had plenty of sargassum washing ashore, the eastern side was clear.

Keep looking, ask around, or check local web-cams, such as these in the BVIs, to get a first-hand account.

Another thing to keep in mind? Tourism is important in the Caribbean. I would expect public officials have plans to try and keep some beaches clean, especially those that are heavily reliant on tourism. Those beach bars need to keep pouring tropical drinks to sunburned customers!

Get the latest scoop when you arrive and be flexible. I promise you that you’ll find your own piece of paradise, sargassum free.

Catching sargassum
Clearing sargassum weed from our lures on a recent bareboat charter trip

Going fishing? Change your tactics.

On our recent USVI and Spanish Virgin Islands sailing trip we caught some fish, but not as many as we had hoped. I’ll blame the sargassum. Nearly every time we reeled in to check the lures, we were dragging sargassum.

Unfortunately, there’s not much you can do if you plan to troll a couple lines in between anchorages. These tips, however, might help:

  • Check the lines more frequently than you otherwise would

  • Don’t put the lures too far back, so it’s easier to reel in and check

  • Skip the diving lures: when they grab sargassum, the resistance can make it really difficult, and time consuming to reel in and clear. Stick to surface skirts

  • Put out a smaller spread: this last trip we had 4-6 lines in the water. That’s a lot to check and clear. Stick with 2-3 and you’ll have more of an enjoyable time.

Other advice? Heave-to, stop the boat, and cast or use a jigging lure. Throw some leftovers in the water as chum. While sargassum blobs are bothersome, they also foster marine life. Mahi mahi love to hang out underneath them. You can read more about those techniques in my sailboat fishing guide.

If you have some ballyhoo, you can also try rigging one of these weedless ballyhoo rigs.

Sargassum floating near Barbuda
Sailing past large blobs of sargassum between Antigua and Barbuda on our May 2023 charter trip

Get ready for some DIY maintenance to your sailboat

You are motoring along, and then suddenly one of your catamaran engines dies. Or perhaps an engine alarm is blaring from overheating.

If you’ve gone through sargassum patches, it very well could be the culprit and is a logical starting point to attack the problem.

Troubleshooting the water intake for the engine (or generator) is a great technique to arm yourself with. It might be clogged by sargassum at the intake, at the strainer, or somewhere in between. We even once successfully attacked the “somewhere in between” clog with our dinghy blow-up pump.

If you’re on a bareboat charter, you’ll be much happier spending the few extra minutes to clear these yourself. No one wants to be inconvenienced waiting on a chase boat from the charter company.

Make sure you check during the chart briefing about the proper way to attack this and get the OK for the DIY fix. Cleaning the strainers daily might also be a good preventative measure in sargassum infested waters.

Best of luck fighting through the blobs of sargassum seaweed blooms this season. I’ll report back soon on what we experienced in Antigua. Unfortunately, this is becoming a more regular event in the Caribbean, and we’ll just have manage it. I’m not going to let it ruin my vacation!

The Best Caribbean Bareboat Charter Destinations

Best Caribbean Bareboat Charter Destinations

While far-off, exotic yacht charters might be intriguing, nothing beats a Caribbean bareboat charter destination right in our own backyard.

Tropical sandy beaches, steady trade winds, lazy beach bars, and convenient travel options characterize a visit to these many islands.

And if you’re limited to a week or 10 days, you’ll get to spend more time on your catamaran with a tropical beverage, and less stuffed into a crowded flight.

From Grenada to Puerto Rico, nearly every country in the leeward and windward islands has a Caribbean sailing vacation option for you.

So let’s dive in. If you are still early in your chartering journey, these are the top Caribbean bareboat charter destinations you need to explore. You can visit each many times, and still find new fresh adventure on a return trip.

I’m on my 11th yacht charter (still in my 30s), and I’ve only visited one destination outside of these six (Key West and the Dry Tortugas).

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

British Virgin Islands

Yes, the British Virgin Islands is the obvious choice, but you have to put it first on the list. It’s the global yacht charter capital.

Not only is the BVIs the best place for first-timers, but you’ll find yourself returning year after year. There’s something about it that keeps drawing you back.

I’ve spoken with some old salts that have made over 30 trips!

It’s popularity owes itself to the unique geography, with many islands and bays to explore, sheltered from the trade wind driven swells.

The sailing is predictable and navigation is easy with short, line of sight passages.

Beach bars, restaurants, and amenities galore, the majority of BVI’s economy caters to charterers.

My BVI destination page is a good place to start to learn more about the BVIs.

Devil's Bay beach at the Baths in BVI
Boulders at Devil's Bay | the Baths, BVI
Lagoon and beach at Cow Wreck
Lagoon swimming on the north shore of Anegada
white bay east side jost van dyke
Beach bars line White Bay, Jost van Dyke

Highlights of a British Virgin Islands yacht charter

  • Hike through the gigantic granite boulders at the Baths to Devils Bay

  • Anchor in North Sound and enjoy the sights of one of the finest harbors in the Caribbean

  • Sail offshore to the sunken island, Anegada. Sip cold beverages at rustic beach bars on the beautiful north shore

  • Go Beach Bar hopping for painkillers at famous White Bay, Jost van Dyke

  • Jump into the water from the second deck of the floating pirate ship bar, Willy-T at Norman Island

Sandy Cany sandbar in the Exumas
One of the many sandbars in the Exumas, this one at Sandy Cay

Exuma, Bahamas

Yes, I know, it’s not technically the Caribbean, but it’s close enough.

I love the Exumas for the fishing, solitude, easy travel options from the USA, oh, and those dreamy blues…

This is also more of an advanced sailing destination and I would not recommend it until you have 2+ charters under your belt. You’ll need to anchor more frequently and pay close attention to weather, tides, currents, and depths. We first visited the Exumas on my third sailing trip.

The water in the Exumas is absolutely stunning, with some of the most vibrant turquoise blues I’ve ever seen.

If you want to learn more about the Exumas, check out my cruising guide, or my Exuma destination page.

Pirate's Lair in the Exuma Bahamas on a Exuma Yacht Charter
Pirate's Lair at Warderick Wells in the Exuma Land and Sea Park
Wahoo caught on the drop in the Exumas sound
Catching wahoo on the drop in the Exumas
Staniel Cay anchorage near Thunderball Grotto
Navigating to the anchorage near Staniel Cay and the Thunderball Grotto

Highlights of an Exuma, Bahamas yacht charter

  • Visit the Exuma Land and Sea Park – our favorite mooring field is the Pirate’s Lair

  • Dinghy the mangrove river at Shroud Cay and hike up to Camp Driftwood

  • Pass through a cut to the Exuma Sound and fish the drop for mahi, tuna, and wahoo

  • Cross the Yellow Bank and stop for lunch at one of the many coral heads you’ll pass along the way

  • Grab a peanut colada at Staniel Cay Yacht Club and snorkel nearby Thunderball Grotto

Sunset at Green Beach Vieques
Sunset at Green Beach in Vieques

Spanish Virgin Islands

Part of Puerto Rico, they lie right next to the US Virgin Islands.

If you want to seek out the old school Caribbean vibe, the Spanish Virgin Islands are for you. They are far less popular and developed than their Virgin Island neighbors to the east.

The SVIs consist primarily of Culebra, Culebrita, and Vieques. There are also a number of smaller cayos to explore as well.

You can find two of the most stunning beaches in all of the Caribbean here: Playa Flamenco and Playa Tortugas.

If you want to learn more about the SVIs, I wrote a cruising guide, with more info on the SVI destination page.

View of Culebrita, one of the Culebra anchorages
Tortuga Beach and the lighthouse at Culebrita
Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage
Epic sunset at a Carlos Rosario
Tank at Flamenco Beach
One of the abandoned tanks at Playa Flamenco

Highlights of a Spanish Virgin Islands yacht charter

  • Hike to the abandoned lighthouse at the top of Culebrita for incredible 360 views

  • Sip $2 Medallas from the vendors at Playa Flamenco

  • Snorkel the beautiful reef from your mooring ball at Carlos Rosario

  • Watch an epic sunset over the Puerto Rico mainland at Green Beach

  • Take a bioluminescence kayak tour at Mosquito Bay

Petit Rameau at Tobago Cays
The idyllic Tobago Cays, a must stop in the Grenadines

St. Vincent & the Grenadines

You’ll enjoy easy sailing, white sandy beaches, abundant marine life, and many vintage Caribbean beach bars to help cool you off.

Consider a roundtrip or a 1-way passage south to Grenada. This option avoids a potential uncomfortable upwind slog back to St. Vincent.

Most people don’t spend much time on the main island of St. Vincent – the many unspoiled islands of the Grenadines to the south beckon.

If you want to learn more about the Grenadines, pick up a copy of the Sailor’s Guide to the Windward Islands.

Anchorage at Salt Whistle Bay
The anchorage at Salt Whistle Bay
Petit Tebac
Captain Jack Sparrow's island, Petit Tebac
The lone umbrella at Mopion Island
The lone umbrella at Mopion Island

Highlights of a St. Vincent and the Grenadines yacht charter

  • Visit the stunning Tobago Cays, snorkel the coral reefs, swim with turtles, and arrange for a lobster beach barbeque

  • Anchor at idyllic Salt Whistle Bay and walk along the beautiful palm-lined beach

  • Explore the island where Captain Jack Sparrow was marooned – Petit Tabac

  • Head to Mustique and grab a cocktail at the legendary Basil’s Bar

  • Get your picture taken with the umbrella on the castaway island, Mopion

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Often photographed Trunk Bay at St. John, USVI

US Virgin Islands

During Covid, the US Virgin Islands made a resounding comeback due to travel restrictions elsewhere. Many long-time BVI visitors discovered the USVIs for the first time. Some were pleasantly surprised!

Why is the USVI appealing? Good provisioning options, cheaper prices, and direct flight options are a few reasons.

Consisting of St. Thomas, St. John, and St. Croix, most boaters spend the abundance of their time circumnavigating St. John and visiting the pristine National Park areas.

You can even use it as a jumping off point to explore the Spanish Virgin Islands. Read about how I did this in my recent USVI and SVI bareboat charter trip.

Epic sunset at Magen's Bay, St Thomas, USVI
The lovely bight of Magens Bay
Beautiful fall day at the Maho Bay mooring field on our US Virgin Islands bareboat charter trip
Beautiful day at Maho Bay in the Virgin Islands National Park
Christmas Cove anchorage on our USVI bareboat charter in the US Virgin Islands
Christmas Cove anchorage and a sunset over St. Thomas

Highlights of a US Virgin Islands yacht charter

  • Lounge on the beach at Maho Bay and take in the spectacular surroundings

  • Be adventurous and conduct an offshore passage to St. Croix to visit the pastel-colored town of Christiansted

  • Stroll the lovely town of Cruz Bay and grab a bite to eat or do some shopping

  • Sail the north shore of St. Thomas to the bight at Magens Bay. Simply enjoy the magical scenery or head ashore for a drink at the beach bar

  • Enjoy the solitude of the Salt Pond Bay anchorage – lime away the afternoon or hike for the views at Ram’s Head

Shirley Heights Overlook at the Sunday barbeque during our Antigua bareboat charter
Historic English Harbour in Antigua

Antigua & Barbuda

After spending a lot of time recently in the Virgin Islands and the Bahamas, we recently visited Antigua and Barbuda and absolutely loved it. You can read about the trip here.

Antigua and Barbuda is a single country, located in the southern Leeward Islands near Montserrat and Guadeloupe (potential offshore destinations for a longer yacht charter trip).

This destination has something for every type of crew. Gorgeous beaches (they attest to having 365 of them), offshore fishing, plenty of bars and restaurants, British naval history, reef snorkeling, and some adventure at offshore Barbuda.

Why else do I like this Caribbean bareboat charter destination? It has a great balance of the get-away-from-it-all anchorages that we enjoy, but it also has a great beach bar/nightlife scene.

pink beach in Barbuda
Quiet pink beaches await after an offshore sail to Barbuda
Antigua bareboat charter
Carlisle Bay on a Antigua yacht charter
With 365 beaches, there's one for every day

Highlights of a Antigua & Barbuda yacht charter

  • Sail offshore to Barbuda, one of the Caribbean’s hidden gems; anchor in solitude anywhere along the Caribbean’s longest pink sand beach (11 miles)

  • Relax amongst the reefs at peaceful Green Island

  • Drag some fishing lines and catch mahi, wahoo, or tuna in the deeper water offshore

  • Hike to Shirley Heights for commanding views and some nightlife at their famous Sunday evening bbq parties

  • Gaze at 200 foot mega yachts in Falmouth Harbour or rub elbows with the rich and famous at the establishments ashore near historic Nelson’s Dockyard

  • Arrange for a tour of the frigate bird sanctuary at Codrington Lagoon

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USVI Bareboat Charter: November Sailing Yacht Adventure

USVI Bareboat Charter

Alright, batten down the hatches. This is a detailed trip report with lots of pictures from my recent USVI bareboat charter trip (oh, and we snuck in a couple days to the Spanish Virgin Islands as well).

You’ll get all the juicy details.

My original USVI plan called for a couple crossings to and from St. Croix. However, we had to change our plans when a tropical disturbance passed nearby and veered strong winds into the SE and then the SW.

So instead, we went straight to the Spanish Virgin Islands (Culebra) on our first day, and then later spent a few extra days at St. John.

We had an absolute blast, and I love the prospects of the US Virgin Islands as a future sailing destination again (this was my first time). St. John, especially, blew me away, and we just scratched the surface. We’ll be back for sure!

Frenchtown Marina in St Thomas, where the Waypoints charter base is located as we prepare for our yacht charter sleep aboard
Beautiful evening at the Waypoints charter base in St. Thomas on our sleepaboard night

Arrival and Sleepaboard at Frenchtown Marina

One benefit of yacht charters in the USVI? Travel is much easier with multiple long haul flights direct from the US. In contrast, the BVI airport’s runway is too short and requires a puddle jumper or ferry connection.

After touching down, we were at the Waypoints base within 30 minutes…not bad! We opted to have our provisions delivered by VI Provisioning, despite much cheaper DIY alternatives, such as Cost.U.Less. With later flight arrivals, we paid up for the convenience factor this time.

The rest of the evening consisted of an excellent dinner at the French Quarter Bistro, stowing provisions, and prepping fishing gear for our trip to the South Drop on day 1.

Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage
Our charter yacht, the Lagoon 46 at Culebra in the Spanish Virgin Islands

The charter yacht: Lagoon 46

A couple quick points about our sailing yacht, the Lagoon 46. This was my first time on the 46 but I’ve previously chartered it’s older sister, the Lagoon 450, many times. My impressions?

  • The yacht was a 2020 and in excellent shape – testament to the care provided by Waypoints (formerly CYOA)

  • Motor speed was average at around 7.5 knots and 2,500 rpms with both engines

  • She sailed great! We topped out at 10.5 knots with a following sea, 25 knots of apparent wind, and a reef in the main and jib. On average we were sailing 8-9 knots in these conditions

    • All the sheets are easily manageable from arms reach of the helm station

    • A self-tacking jib is always a plus on bareboat charter trips

  • The flybridge is our favorite hangout area, and this one had improved lounge space compared to the 450

  • Not enough storage! It seemed like we struggled to find places to stow provisions and gear

  • Our version had underwater blue lights, and those are always fun

  • Would have been great if the dinghy winch was electric

First fish of the trip, a barracuda | They love pink lures by the way

Day 1: Itinerary disruption, so off to the shelter of the Spanish Virgin Islands

In the days leading up to our trip, it became clear our plan to sail south to St. Croix was falling apart. There was increasing confidence that a tropical disturbance would pass nearby.

The result?

Strong southerly winds (25+ knots) and lots of rain. If I insisted on a deepwater crossing south in those conditions, I’m confident I would have had a mutiny aboard.

So change of plans. Where did we want to get stuck for 24-36 hours with protection from the south? I know!

Flamenco Beach in Culebra! I’ve always wanted to anchor here off a global top 10 ranked beach, and it looked like we could get at least a day to explore the area before the storm moved in.

Typically this is a day anchorage only because of it’s northerly ground swell exposure. It can also be rolly with stronger easterly trades that wrap the wind swell around into the bay.

So with our charter briefing behind us, we cranked some yacht rock, headed south, and picked up the drop for some fishing before turning west to Culebra. We quickly hooked up a few barracudas, but nothing worth keeping. Sargassum plagued our fishing endeavors most of the trip.

Carlos Rosarion reef at Culebra Spanish Virgin Islands
The reef at Carlos Rosario beach in Culebra
Our first USVI bareboat charter sunset in the Spanish Virgin Islands
Enjoying our first night's sunset at Carlos Rosario

We pre-loaded the necessary check-in info into the CBP Roam app. Once inside Ensenada Honda, we submitted our arrival. The whole process took only about 10 minutes to clear in, with a quick video chat for the one crew member didn’t have a known traveler number. With little interest in sticking around Dewey and Ensenada Honda, we went back out the channel and up the west coast of Culebra to Carlos Rosario.

After carefully checking the mooring ball (it’s a bit deep to anchor, and the bottom is coral), we decided to stay the night.

The snorkeling here is excellent, one of my favorite places. Did I mention epic sunsets over the cayos to the west?

Not bad for the first day. We celebrated with a few Caribs and Costco filets we froze and brought with us on the flight.

Our catamaran at anchor at Playa Flamenco
Our anchorage at the NE corner of Playa Flamenco

Day 2: Off to explore Culebrita and Flamenco Beach

With about 12 hours before the rain started moving in, we slipped our mooring lines and motored north around Culebra. We wanted to first check out the viability of Flamenco Beach as a 2-night overnight stop to shelter us from the approaching storm.

Trolling on the way, we reeled in a bonito, but not much else.

Bonito caught north of Culebra
Bonito we caught trolling on the shelf around Culebra

We poked into the anchorage area on the NE corner of the beach. Roll was minimal on the catamaran with winds already starting to veer into the south. With no approaching northerly swell for 48 hours, it would be a perfect place to hang out.

Before dropping the hook, we set out for a lunch stop at Culebrita, one of the prettiest beaches in all of the Virgin Islands. On our way, motoring through the channel next to Cayo Norte, we hooked, but couldn’t reel in, what looked to be a large wahoo, or perhaps a kingfish. Tough luck!

View of Culebrita from our anchorage
View of Culebrita on a quiet day as the storm approaches

There were a couple tour boats from Puerto Rico at Playa Tortuga, but they left soon after our arrival, leaving the place largely to ourselves.

We didn’t make the hike to the lighthouse this time, but settled for swimming ashore and floating in the beautiful water. And of course, we were visited by several turtles that call this bay home.

Sargassum is heavy on the west side of Flamenco Beach in the Spanish Virgin Islands
Lots of sargassum on this visit! But, only on the west side of the beach
Target practice tank at Playa Flamenco on our USVI bareboat charter trip
Hide tide at Playa Flamenco
Kiosks at Playa Flamenco where you can buy cheap Medallas
Kiosk vendors at Playa Flamenco where you can buy cheap Medallas

Back at Playa Flamenco, we took the dinghy ashore to check out the target practice tanks and grab a Medalla from the local vendors.

I’d heard of an unusually heavy year for the sargassum in the Caribbean. The west side of Playa Flamenco was the first victim that we saw on this SVI and USVI bareboat charter trip.

Wow! This was the most I had seen on a beach before, and it definitely takes away from some of the magic of this place.

Rain squalls on our USVI bareboat charter trip
We awoke to heavy squalls as the tropical disturbance moved in

Day 3: Riding out the storm at Flamenco Beach

We awoke to heavy rain squalls as the disturbance approached, and they persisted throughout much of the day. But, that didn’t stop us from fishing!

Using a sabiki rig, we hooked several bait fish. We saw a quick window in between thunderstorms, so we went out for a trolling trip around Cayo Norte.

We live baited the fish and moved slowly at around 3-4 knots. Alas, nothing memorable and we had to settle for riding out a squall before returning to our anchorage at Flamenco Beach.

Fishing in the rain at Playa Flamenco
Rain squalls couldn't stop us from fishing
Riding out a squall in the US Virgin Islands
Riding out a squall while we were fishing north of Culebra

What else to do while it was pouring? Well, we threw up the projector, set up a wifi hotspot, and streamed the World Series on the big screen.

Not a bad place to watch and celebrate the Astros win!

Watching the Astros win the World Series on the yacht on our USVI bareboat charter trip
Astros win the World Series!

Yacht Charter Day 4: The storm breaks and we sail to Magens Bay, St. Thomas

Clear skies at sunrise after the storm on our USVI bareboat charter
Sunrise departure from Playa Flamenco

We arose at sunrise and weighed anchor for a long day on the water. This was just in time as a forecasted northerly swell had just started to move in. Flamenco Beach is not the place to be when a swell is running!

Back around the west side of Culebra. We wanted to check wind and swell conditions in the unlikely event it was comfortable enough of a ride to attempt the crossing to St. Croix. Nope! Despite southwest winds, the seas were still very much confused with the addition of a northerly swell.

OK, now where to? The wind direction was perfect to sail all the way around the northern side of St. Thomas to beautiful Magens Bay. With 25+ knots of apparent wind, we tucked in a reef in the main and the jib.

Sailing from Culebra to St Thomas with reefed sails

This was probably one of the most fun sailing days I’ve had on a yacht charter trip. The catamaran was easily cruising along at 8 knots and clocked 10+ later in the day with following seas as we surfed the swell.

Our helmsman did have to take over hand steering as the autopilot wasn’t able to keep up with these rollers.

We put 4 rods out and 2 handlines. Clearing sargassum was frustrating, and I think that definitely affected our fish count this trip. However, we had some good luck when trolling over the Grampus Banks. We hooked up on a cero mackerel and landed it. Finally, a fish worth eating! Cero mackerel is considered one of the top sushi eating fishes out there.

Here’s a video of us reeling it in.

Magen's Bay USVI bareboat charter anchorage during a USVI sailing itinerary

At Magens Bay, we dropped anchor in about 30 feet. The yacht spun around quite a bit in this anchorage with strong winds still blowing out of the south and some backwinding in effect.

The anchorage was shared with a couple other boats, but we had plenty of elbow room. Some charter crews have complained about loud music and jet skis here, but we didn’t experience any of that.

The bay is truly stunning, and I’d recommend this anchorage to anyone planning a USVI bareboat charter.

To take the edge off a long day on the water, we took the dinghy ashore and cooled off with a bushwacker at the beach bar ashore. Back on the boat, we whipped up some cero mackerel sashimi for an appetizer, and sauteed mackerel with cilantro lime rice for dinner. Delicious!

Beautiful fall day at the Maho Bay mooring field on our US Virgin Islands bareboat charter trip
The gorgeous mooring field at Maho Bay

Day 5: Off to the beautiful beaches of St. John and the Virgin Islands National Park

OK, where to next? St. John was the logical next destination. We hadn’t planned to spend much time sailing the Virgin Islands here on this bareboat charter trip, but our inability to get down to St. Croix changed that.

Before setting off, we grabbed a taxi and made a quick run for a less expensive provisioning run at Cost.U.Less. Things would certainly have been more expensive at Cruz Bay, St. John. It took about an hour round trip, and was well worth the effort.

With lighter winds, we settled for motoring and cruised around the Hans Lollik islands just to the north. They are beautiful, and uninhabited, but we decided not to stop (there are 2 anchorages in settled conditions).

St John sunset on our USVI bareboat charter trip
Another great Virgin Islands sunset | Too bad I couldn't put up the drone in the National Park!

We slowly motored along the north shore of St. John close to the British Virgin Islands and took in the gorgeous surroundings. The Virgin Islands National Park is truly stunning. Maho Bay called to us with it’s busy beach and crews floating off the back of their charter boats. After being isolated for so long during the storm, we were ready for some people watching!

A cooler was packed, and ashore we went in the dinghy to chill out and have a beach day. We settled for liming away for a few hours and enjoyed the evening sunset show back on the catamaran.

North shore of St. Johnm
North shore of St. John looking west

Day 6: More beaching and a night out in Cruz Bay

After a lazy morning, we decided to stay put after having so much fun on the beach the previous day. Maho Crossroads is a good option for to go beach bar fare to eat on the sand.

Sometime mid morning, a sailboat caught fire to our west. The crew got out safely from the traffic we heard on the radio.

Sailboat fire north of St. John USVI
Sailboat fire we saw to our west

Later in the afternoon, we were ready for a change of scenery, and perhaps a night where we didn’t have to cook. With that in mind, we motored back west to moorings at Caneel Bay. Cruz Bay was redlined by our charter company and this was the closest overnight anchorage.

80s Night in Cruz Bay USVI
Some of our crew ready for 80s night in Cruz Bay

We donned our best 80s gear and dinghied into town for a couple drinks and dinner.

Cruz Bay was so much fun! The people were friendly and it has a great local vibe. We started and ended the evening at The Beach Bar (yes that’s it’s name) where we had beached our dinghy. Did you say live music and dancing??

Christmas Cove anchorage on our USVI bareboat charter in the US Virgin Islands
The anchorage at Christmas Cove near St. Thomas

Day 7: Last day of the USVI bareboat charter: more fishing and back to St. Thomas

We rubbed our bleary eyes and cruised back around the north shore of St. John before heading down to the South Drop for some trolling. Again not much on the fishing count to report! In fact, I don’t think we had any bites on the over the drop itself, just on the shelf.

Oh well, it was still fun getting the sails up for a couple hours on the water.

As a last night’s anchorage, we chose the Christmas Cove mooring field. On our last morning, it would only be an hour motor back to Frenchtown Marina. I had thought Pizza Pi VI would be back in action for the season, but I think we were a few days too early.

Christmas Cove was fine, but it was probably my least favorite anchorage of the trip. Besides the convenience, there just really wasn’t much to do there. There are no beaches, the mooring balls are close together, and the snorkeling wasn’t that interesting.

We did have some catch and release fun with a school of jacks that hung around the boat and our blue underwater lights.

Had I another shot with my USVI sailing itinerary, I probably would try Water Island next time.

The sunset over Red Hook, St. Thomas, however, was pretty epic.

Check-out day: A smooth return of the catamaran

Not much to report for our last day, which is what you want! After a short motor back to the Charlotte Amalie area, we stopped at Crown Bay Marina to refuel. We raised them on Channel 16 and were able to come right in. The fuel dock is immediately to starboard after entering.

Back at Frenchtown Marina, we grabbed one of the Waypoints moorings and notified them by cell phone. The Waypoints team quickly came out to conduct the sail check before handling the med mooring back on the dock.

The check-out briefing also went smoothly and only took about 20 minutes.

I can’t wait to visit the USVIs on a bareboat yacht charter again! On our next BVI charter, I would even think about hopping over to St. John for a couple days. While the British Virgin Islands get most of the attention, crews should give USVI a closer look!

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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
  • 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.

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.

Interested in a Spanish Virgin Islands Yacht Charter?

We have relationships with the Spanish Virgin Islands yacht charter companies and have personally chartered with them.
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Final Preparations for a Yacht Charter Trip

Boat Trip Planning - watching the weather models

We are just weeks away from my next bareboat yacht charter trip – this one is a bit different. The plan is to sail the US Virgin Islands and Spanish Virgin Islands, including a couple deepwater crossings to and from St Croix (weather permitting!). We are also going to do a lot of fishing from the catamaran.

You can read more about my plan in this post, Sailing to St. Croix.

I’ll post some regular updates at the Yacht Warriors instagram account if you’re interested in following along.

To ensure a smooth, and (hopefully) stress free trip, we are always busy with final plans and preparations in the days leading up to a trip. I thought I’d share some of what I’m working on.

Boat Trip Planning - watching the weather models
A possible disturbance popping up that could affect our sailing itinerary | Source: Tropical Tidbits

Watching the weather like a hawk

The trend is your friend. This is especially true when chartering during hurricane season. While November is well past peak season, disturbances can still spin up.

In recent days, I’ve consistently seen several storms showing up on longer range weather models. One has turned into Potential Tropical Cyclone 15 which will move on to the west and be a non-issue for us.

There is, however, another weak disturbance that could bring 30 knots of wind during the middle of our trip.

It’s too early to tell exactly what impacts it could have, but I like to watch the trends and see how the forecast evolves. If confidence builds for that scenario, we’ll want to make sure our itinerary includes an anchorage where we can hunker down for 24 hours or so.

As we get closer to our departure day, I’ll start watching NOAA’s 5-day marine forecast. This should give you a good idea as to conditions you are likely to experience.

Weather routing on a crossing to St Croix
Example of what an unfavorable forecast could be crossing to St. Croix, with moderate SSE winds | PredictWind

For the crossings to and from St. Croix, we may need to adjust our itinerary for days with more favorable conditions. Or, we may have to cancel those plans all together. Under what conditions would I want to change those plans?

  • 20+ knot winds – this could make for a rough ride

  • Light wind, less than 10 knots – we don’t want to motor

  • Unfavorable wind direction – while the trades tend to blow out of the NE in the fall/winter, they can be bent further into the SE or S with passing disturbances

At the base on a previous charter trip getting ready to board, this one at Scrub Island in the BVIs

Final communications with the charter base

I always like to try and connect directly with the charter base if possible, in the days leading up to our departure. You’ll need to try and find the right contact – it’s usually not the charter specialist that helped book your trip.

There are two objectives:

  1. To try and position ourselves first in line for the charter briefing the morning after our sleepaboard. This can be the difference between leaving the dock at 9:00, or departing two hours later at 11:00. This doesn’t always work, but you miss every shot you don’t take.

  2. To confirm boat equipment, such as portable a VHF radio, rod holders, gaff, type of grill, etc.

For the first time, we are experimenting bringing our own frozen meats with us

Getting the crew involved

As the skipper, don’t try and do everything yourself! Most people love to help out and enjoy getting involved. Here are some activities I’ve delegated for this trip.


This is a great one to delegate to one or two crew members that have some logistics savvy.

By this time, we usually have finalized our menu plan and detailed list. The final step is coordinating for delivery of the food, beverages, and booze.

Or, there may be certain items that may need to be picked up in person. Each sailing destination is different.

For the US Virgin Islands, our crew decided delivery of everything with one company to be the best option since we have late arriving flights. If we had arrived earlier, you can really save quite a bit by shopping in person. We are paying extra for the convenience factor.

The USVIs also have several options where you can order online and just show up for curbside pick up – a good compromise.

We are also trying our hand at bringing frozen meats with us for the first time. We picked up some filets from Costco and pre-cooked some other meals like taco meat and chicken. TBD if it is going to be worth the extra effort ahead of time!

fresh mahi caught on a sailboat during a bvi yacht charter
Mahi we hooked previously on a trip in the Virgin Islands

Fishing licenses & regulations

There’s a lot to navigate when it comes to fishing in the USVI and Spanish Virgin Islands. There are federal waters (>3nm offshore), territorial waters, and the Virgin Islands National Park. Each has its unique license requirements, seasonal closures, and bag limits.

Additionally, there are numerous marine parks and protected areas that we’ll be passing through, such as the Coral Reef National Monument, East End Marine Park, and Hind Bank.

While at this point we are all familiar with the various rules, we have one crew member that is our designated expert to help make sure we fish lawfully throughout the trip.

Clearing customs into Culebra

We are required to clear customs when entering Culebra (Puerto Rico) from the USVI. Since we are all US citizens, this can be accomplished remotely with the CBP ROAM App.

One crew member has taken the lead in getting the app setup with the correct vessel and passport/known traveler numbers.

While I’m focused on navigating through the Ensenada Honda channel and getting us anchored, they can begin the check in process with CBP.

Sailing to St Croix: East End on St Croix USVI
View of the east end of St Croix with Buck Island in the distance

Buck Island Permit

We are going to sailing south to St. Croix, and one of the attractions is the Buck Island Reef National Monument. To visit though, you need anchoring permit.

I had a crew member help by obtaining the vessel registration and submitting the permit to the National Park Service for approval.

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…


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.


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.


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

Here’s a few pictures of a fresh ballyhoo we caught with a sabiki rig after chumming the water behind our cat at anchor. I also rigged this one up with an Ilander torpedo style skirt.

Rigging a ballyhoo during our Antigua bareboat charter
Getting ready to put this in the water while we were sailing between Barbuda and Antigua
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
fishing a large sargassum patch on our sailboat in Antigua
Jigging on a large sargassum patch near Barbuda

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.

Fish of the Virgin Islands

Fish of the Virgin Islands

The fish of the Virgin Islands are similiar to what you can expect elsewhere across the Caribbean, from the Bahamas to Grenada.

Many of them, are delicious eaters, and others, fierce fighters.

If you’re planning a yacht charter or are thinking about booking a fishing trip, these are the fish you are most likely to encounter in the Virgin Islands. That includes the British Virgin Islands, Spanish Virgin Islands, and US Virgin Islands.

If you want to learn more about fishing techniques in the Virgin Islands, check out my tackle and fishing technique recommendations here.

Offshore fish of the Virgin Islands

Location: north and south drops, or in the deep water between St. Thomas/St. John and St. Croix.

Offshore is my favorite place to fish in the Virgin Islands. We typically head out to the north or south drop and troll back and forth in 200 to 600 feet of water.

Since we are usually sailing, we’ll have two lines out – one surface lure such as an Iland Ilander skirt. The second is a diving lure such as the Yozuri Bonita.

Here are the offshore fish species you can expect to catch:


Exuma fishing tips: filleting a wahoo in the Exumas
Here I'm fileting a fresh caught Wahoo to prepare it for sashimi and poke bowls on the catamaran
Fresh caught ono poke bowl
Wahoo poke bowl

Wahoo is by far my favorite eating fish that we catch. It’s great as sashimi and in poke bowls, or grilled up in fish tacos.

The wahoo fishing is always better in the fall, beginning in November, although it’s possible to hook one anytime of the year.

Since they claim to be the fastest fish in the ocean, they are also a lot of fun to fight. On my last trip, a huge one ran out most of my line and then snapped the 80 pound braid!

We’ve always had more success with wahoo using diving lures that swim 15+ feet below the surface of the water, such as the Yozuri or Rapala X-Rap Magnum.

Mahi Mahi (dolphin fish)

Filleting a mahi mahi caught in the Virgin Islands
Shot of me filleting a schoolie mahi mahi caught on a shelf area near the South Drop

Mahi are unmistakable with their shades of green, yellow, and blue.

You can catch mahi year round, in the shelf areas, as well as offshore.

Look for floating debris or sargassum – they don’t like the sun and enjoy shading themselves beneath. If you can see them, stop the boat and cast a popper lure near them. They can’t resist.

Mahi always become great candidates for fish tacos on our yacht charter trips. They are also excellent sauteed and crafted into a sandwich.


Yellowfin tuna

Yellowfin tuna are also easy to identify with the yellow markings and distinctive sickles. They can get quite large, compared to their cousins the blackfin and skipjack. Skipjack can be distinguished from blackfin with their horizontal stripes on the belly.

Tuna can be targeted by trolling using skirts and diving lures. If you see birds attacking a bait ball, that’s also a good sign tuna can be near.

Yellowfin is the best eating tuna, but all three are worth eating. Straight up with some soy sauce or cooked rare is the way to do it.



Blue marlin hooked up

Honestly, I’m not ever intentionally targeting marlin. If we ever caught one it would surely be released. I really don’t want to have a several hour battle either since we usually have a lot of ground to cover on our sailing trips (such as my crossing from St. Croix to Culebra on my Fall 2022 trip).

They can be caught in the Virgin Islands though, and it’s great fun if you have the right equipment and sportfishing boat.

Try pulling some bird teasers behind the boat to help raise them to your lures.

The size of the marlin that can be caught on the north drop is something of legends. You can also encounter marlin in the deepwater between St. Thomas/St. John and St. Croix.


Sailfish are typically caught for catch and release beginning in the fall months when the water begins to cool.

If you know where to look, you can see them surfing swells at the surface when their distinctive sail breaks the water. Anglers can then target sailfish by casting a surface lure or live bait to them.

Inshore Virgin Islands fish species

Location: shelf and reef areas, <150 feet

Inshore areas are great for bottom dropping, drift fishing, or fishing off the back of the boat while at anchor.

If shallow enough (I’m only a beginner at spearfishing), we’ll hop in and try and shoot with with a Hawaiian sling or speargun.


Catching barracuda in the Caribbean

This is, without a doubt, the fish we catch most frequently while trolling. They just can’t resist my lures, I guess!

They are fun to catch, but not the ones we want to eat. With the potential for ciguatera poisoning, especially the larger ones, we always release them. 

Another reason we don’t eat them? They smell…apparently the meat doesn’t but their skin is another story.


King mackerel caught in Key West
King mackerel we caught in about 50 feet of water

I’ve yet to catch a spanish mackerel, but for some reason we have hooked plenty of king mackerels. You can tell the difference since the spanish mackies have distinctive yellow spots.

We recently caught a cero mackerel on our USVI and SVI trip – it made excellent eating! They look pretty similar to spanish mackerels, but have a distinctive stipe.

Spanish/cero mackerels are the better eating fish. King mackerels are oily and require a different type of preparation, such as by smoking.

Toothy fish, similar to the wahoo and barracuda, you’ll want to use a wire leader if you think you might hook one.

Bonito (little tunny)

Little tunny caught near key west florida
Little Tunny that I caught and released using a Iland Illander surface lure

Another fish on my list that we catch and release. I’ve just heard the meat is not that great to eat. They are shaped like tuna, but you can identify them by the squiggly dark lines on their back.


Jack caught in the Virgin Islands
Jack we caught with a surface lure while trolling over a reef in 50 feet of water

There are many different types of jacks. I think some are good eating, but I don’t have a sharp enough eye yet…we typically catch and release them if we hook one.

They can be caught while trolling and also while spear fishing.


Small grouper caught in the US Virgin Islands
Small grouper we released in Culebra

Grouper is one of my favorite fish to eat.

Again, there several species, such as the black grouper and red grouper. You’ll want to make sure you are in compliance with fishing regulations. Sometimes there are certain seasons for these type of fish.

Also make sure you don’t keep any goliath groupers – they are typically off-limits all year round. Worth checking out the nassau grouper too, they are sometimes off-limits.

Groupers are best hooked while spearfishing or bottom dropping.


Snapper we caught in the Spanish Virgin Islands

Snapper is another great eating fish. The three most common you might encounter are yellowtail, mutton, and mangrove.

I’ve hooked both mutton and yellowtail before while trolling over a reef, but they are easier to target by spearfishing or bottom dropping.

Yellowtail snapper also like to congregate underneath your yacht. You can even chum the waters to attract them with leftover meal scraps. If you see this, put on some light fluorocarbon leader and some dead bait – you’re likely to get a bite quickly!


Tarpon under the yacht in the US Virgin Islands

You’ll often see tarpon in marinas near the areas where they throw fish scraps. In the British Virgin Islands, they like to hang out at Saba Rock, where they do a daily feeding.

These are definitely not eating fish – the meat doesn’t taste very good and the tarpon are quite bony.

You might, however, catch one if you drop a line down with dead bait in your anchorage. They are ferocious fighters and fun to catch!


Catching lionfish in the Exumas
Lionfish we speared on a reef in the Bahamas
Fresh caught lionfish ceviche
Lionfish ceviche appetizer on the boat - delicious!

Lionfish are in invasive species and can be taken any time of year. They don’t get very big, but the meat is excellent!

Spearfishing is the way to catch these suckers. For beginners, they make excellent targets since they aren’t afraid and don’t try to evade you (since they have no predators).

Check out my post about lionfish ceviche that we recently made in the Exumas. It has some cautionary notes about removing the venomous spines (painful but not life threatening).

Spiny Lobster

Fresh grilled Anegada spiny lobster
Fresh grilled Anegada spiny lobster on the boat | We got these from a local since tourists are not allowed to take them

Ok, not a fish, but worth mentioning.

Make sure you check local regulations, they differ, for example, between the USVI and BVIs. In the BVIs, tourists are not allowed to take them at all.

When in season and legal, we use a tickle stick and net to coax them out of their hideouts. A snare is also a good method.

Nothing beats fresh spiny grilled lobster with an epic Caribbean sunset (we’ve tried boiling too – grilling is better!).