Best Caribbean Islands For Sailing

Follow in the footsteps of great explorers, sail the waters of history's most infamous buccaneers and chart a course through pirate territory on the legendary Caribbean Sea. From a simple catamaran to a luxury cruising yacht, sailing the Caribbean lets you experience the world's most spectacular islands from every angle.

Where: British Virgin Islands

Considered the world's yachting capital, the British Virgin Islands archipelago consists of 25 islands and hundreds of secret bays and hidden coves. Once dominated by pirates and privateers who preyed on Spanish galleons bound for Europe, these waters are now the playground of experienced sailors, vacationers captaining their own bareboats, island hoppers and luxurious crewed charter vessels.

Where: The Grenadines

The Grenadines consist of 32 islands and cays stretching south from St. Vincent to Grenada. Only nine of these are populated. Set sail from the former pirate capital of Bequia in the north and voyage to Carriacou in the south and on the way, experience the tranquil warm waters and gentle trade winds that have enticed generation of sailors to this part of the Caribbean.

Where: St. Lucia

With the warm waters of the Caribbean on one side and the depths of the Atlantic Ocean on the other, St. Lucia is a natural stepping off point for Caribbean sailing adventures and has been for centuries. At Marigot Bay and Rodney Bay marinas, sail boats and yachts for every budget can be chartered to navigate the surrounding islands of the West Indies.

Where: Antigua and Barbuda

Antigua and its sister island of Barbuda boast some 365 beaches (one for everyday of the year) and there are enough anchorages and harbors to entice you to cruise here for a month or more without going to the same place twice. Famous for sailing and yacht racing, Antigua celebrates the sea in late April each year during its Sailing Week. They also host a Classic Yacht Regatta, a series of international races and a weekly "after work" Thursday afternoon race for all. Antigua and Barbuda offers all the types of charters including bareboats, crewed yachts, catamarans, sailboats and luxury yachts.

Where: St. Martin

Whether you choose a sunset cruise, an afternoon of crewing aboard an 12-meter class America's Cup yacht, a day trip aboard a catamaran or you charter a yacht for a week of sailing around nearby St. Barts and Anguilla, St. Martin is an ideal sailing base. At the northern tip of the Leeward Island chain, the region has always beckoned sailors with the promise of great cruising and just the right amount of challenge.