Caribbean

Popular Caribbean Yacht Charter Destinations

The British Virgin Islands

Known as the “Sailing Capital of the World,” the BVI offers 60+ islands, from the granite boulders of The Baths to the legendary beach bars of Jost Van Dyke — ideal for protected, line-of-sight sailing.

US Virgin Islands

Upscale convenience meets natural beauty: St. John’s national park waters, St. Thomas’s lively port, or St. Croix’s history and diving further south.

Antigua and Barbuda

365 beaches, home to historic Nelson’s Dockyard, blending colonial heritage with world-class regattas and Barbuda’s untouched pink sand.

St. Martin and St. Barths

French and Dutch culture in St. Martin pairs with the chic, high-end lifestyle and Michelin-starred dining of St. Barths.

St. Vincent and the Grenadines

32 islands off the beaten path. Swim with sea turtles in the Tobago Cays Marine Park, then anchor at the old-world harbors of Bequia and Mustique.

Grenada

The ‘Spice Isle’ welcomes you with nutmeg and cocoa, lush mountain interiors, hidden waterfalls, and the colorful harbor of St. George’s.

British Virgin Islands (BVI)

Embarkation is almost always Tortola. A typical week covers Virgin Gorda, Anegada, and Jost Van Dyke, with reliable trade winds and calm, sheltered bays that make the BVI the easiest sailing ground in the Caribbean for first-time charterers. See the 7-day BVI sailing itinerary or the BVI yacht charter page for available boats.

Best for: First-time guests, families and catamaran charters

US Virgin Islands (USVI)

Embarks from St. Thomas, a short sail from the BVI – many guests combine both island groups into one one-way trip. St. John’s protected national park waters and St. Croix’s diving further south round out the group.

Best for: U.S. travelers, families and shorter itineraries

Antigua

Best reached with a direct flight, especially during Antigua Sailing Week season. Fewer sheltered anchorages than the BVI, but excellent marinas and provisioning make it a strong base for both racing and cruising.

Best for: Sailing enthusiasts, beaches and shore experiences

The Leeward Islands

St. Martin, St. Barths, and Anguilla form an island-hopping route best suited to guests prioritizing dining, nightlife, and duty-free shopping between stops.

Best for: Dining, nightlife, luxury island-hopping, beach clubs, and duty-free shopping.

The Windward Islands

St. Lucia, Martinique, St. Vincent, the Grenadines, and Grenada call for longer passages and suit more experienced sailors chasing rainforests, waterfalls, and volcanic beaches with fewer crowds

Yacht charters in the Caribbean offer an unmatched way to explore the region’s islands and cultures – from the lively and social to the serene and untouched. Compare every option on our Caribbean destinations page.

Best for: Scenic cruising, nature, longer passages, remote anchorages, and experienced charter guests.