Best Caribbean Destinations for Yacht Charters

These Caribbean yacht charters are the best way to island hop.

Planning to island hop? A sailing charter through the Caribbean is the best way to do it. Not only will you hear the calming sounds of the ocean waters gently splashing against the sides of your chartered yacht, but you’ll do so in luxury, style and comfort. Combine that with the joy of discovering someplace new, and you have a Caribbean sailing charter that won’t soon be forgotten.

Wander through the lush, tropical environments of the Spanish Virgin Islands. Or consider hiking a volcano on St. Vincent and the Grenadines. Ever wanted to try a true painkiller, straight from the source? Head to Jost Van Dyke’s White Bay and its Soggy Dollar Bar.

Here are some of the best Caribbean charter destinations that will take you through some of the lushest islands and hidden gems.

The British Virgin Islands

The British Virgin Islands
The British Virgin IslandsShutterstock

Often thought of as the boating capital of the Caribbean, the British Virgin Islands are paradise found. Snorkel tiny coves cradled within leafy, castaway cays, or hit the popular Virgin Gorda Baths or Norman Island Indians. Palm-shaded hammocks await on Jost Van Dyke's White Bay, home to the Soggy Dollar Bar and its famous Painkillers.

Considering a bareboat yacht charter? The British Virgin Islands is the place to begin, as the protected waters of the Sir Francis Drake Channel are ideal for novice sailors. It’s easily one of the best destinations to book Caribbean yacht charters.

The Windward Islands - St. Vincent and the Grenadines

The Windward Islands: St. Vincent and the Grenadines
The Windward Islands: St. Vincent and the GrenadinesShutterstock

Mesmerizing in their beauty with a rich French-English-Creole heritage, the 40-mile island chain known as the Windwards are verdant and tropical. With beautiful, secluded anchorages, the volcanic islands of St. Vincent and the Grenadines are all fairly close together so you’re never out of sight of land.

Hike La Soufrière, a volcano on spectacular Bequia, pick up a mooring on secluded Petit Mustique, or snorkel the prolific waters of Tobago Cays Marine Park. Caribbean yacht charters often begin on either St. Lucia or St. Vincent.

The Leeward Islands - St. Martin, Anguilla, St. Barts, St. Kitts and Nevis

The Leeward Islands: St. Martin, Anguilla, St. Barts, St. Kitts, Nevis
The Leeward Islands: St. Martin, Anguilla, St. Barts, St. Kitts, NevisShutterstock

Ninety miles east of the British Virgin Islands, the Leeward Islands are a mix of 18th-century colonial history, European heritage and laid-back Caribbean charm. For more traditional island hopping, boaters can easily spend a week traveling between St. Martin, Anguilla and St. Barts.

Visit the vibrant Creole market in Marigot, St. Martin’s French capital, anchor at Colombier on the quiet tip of glamorous St. Bart’s, and snorkel Pelican Point in Aguilla’s Crocus Bay. With 10 days, add stops on the unspoiled rainforest islands of St. Kitts and Nevis.

The Spanish Virgin Islands

Best Caribbean Islands for Sailing Charters | Culebra Puerto Rico
The Spanish Virgin IslandsShutterstock

While everyone else makes plans to hit the well-known Caribbean yacht-charter destinations, you can escape the hullabaloo in the Spanish Virgin Islands. Just six miles southeast of Puerto Rico, the Spanish Virgin Islands are mellow and laid-back in the way the British Virgin Islands were 30 years ago.

This lesser-known tropical eden is made up of Vieques and Culebra along with tiny islets and cays like Isla Culebrita, Isla Palominos and Cayo Luis Peña. Spend a day lounging on Culebra’s secluded Bahia Tortuga, stroll along the Malecon waterfront in vibrant Esperanza on Vieques, or take an evening kayak tour through the bioluminescent waters of Puerto Mosquito.