Caribbean Sailing
Discover the world’s most famous sailing destination where steady trade winds, warm waters, and countless islands create the perfect tropical sailing experience.
100+ Islands
Trade Winds
Year-round
Sailing Regions
British Virgin Islands
December - May
World’s premier sailing destination with protected waters and short distances
Tortola
Virgin Gorda
Anegada
Jost Van Dyke
Windward Islands
December - April
Mouantainous islands with lush rainforests and dramatic volcanic landscapes
St. Lucia
Martinique
Dominica
St. Vincent
Leeward Islands
November - May
Sophisticated sailing with luxury resorts and pristine beaches
Antigua
St. Barts
St. Martin
Anguilla
Sardinia
Grenadines
December - April
Spanish island paradise with vibrant nightlife and hidden coves
Bequia
Mustique
Tobago Cays
Union Island
Barbados Circuit
January - May
Perfect trade wind sailing around the easternmost Caribbean island
Bridgetown
Speightstown
Bathsheba
Oistins