Matt Weidert
The 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).
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.
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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
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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.
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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
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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.
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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
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.
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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
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.
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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
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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.
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
