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).
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.
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
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.
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
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.
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
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.
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
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.
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