fbpx Skip to content

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.

If you are still early in your chartering journey, these are the top 5 Caribbean bareboat charter destinations you need to explore. They are the best sailing trips for beginners.

You can visit each many times, and still find new fresh adventure on a return trip.

I’m on my 9th yacht charter (still in my 30s), and I’ve only visited one destination outside of these top 5 (Key West and the Dry Tortugas).

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma)
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 FAQ page is a good place to start to learn more about the BVIs.

Boulders at Devils Bay at the Baths
Boulders at Devil's Bay | the Baths, BVI
Lagoon and beach at Cow Wreck
Lagoon swimming on the north shore of Anegada
White Bay JVD
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

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, and easy travel options from the USA.

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.

Pirate's Lair anchorage at Warderick Wells
Pirate's Lair at Warderick Wells in the Exuma Land and Sea Park
Shroud cay anchorage and the mangrove river
Aerial view of the mangrove river at Shroud Cay
Wahoo caught on the drop in the Exumas sound
Catching wahoo on the drop in the Exumas

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 suggest Stephen Pavlidis’ Guide to Puerto Rico. You can also check out my cruising guide.

View of Culebrita, one of the Culebra anchorages
Tortuga Beach and the lighthouse at Culebrita
Tank at Flamenco Beach
One of the abandoned tanks at Playa Flamenco
Carlos Rosario sunset in Culebra
Epic sunset at a Carlos Rosario mooring ball

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

This is the only destination on my list I haven’t yet visited. We had plans, but were disrupted by Covid.

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

You can do 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 Tebac

  • 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

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. Many were pleasantly surpised!

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.

Magens Bay USVI in St Thomas
The lovely bight - Magens Bay
Picturesque Dutch-inspired Christiansted in St. Croix
Beautiful Caribbean town of Christiansted, St. Croix
Ram Head and Salt Pond Bay

Highlights of a US Virgin Islands yacht charter

  • Lounge on the beach at Trunk Bay, the most photographed spot in the Caribbean

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

  • Stroll the lovely town of Coral 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

Thanks for reading my post about the best Caribbean bareboat charter destinations! If you enjoyed it, please subscribe or check out some of my other articles, like this one about how the British Virgin Islands’ vibe is changing.