Charting a Course for the Best Sailing in the Caribbean

  • 01 of 06

    Set Your Sails for the Best Sailing Trips in the Caribbean

    sailing yacht in Antigua
    Photo via Pixabay

    If you plan to go sailing in the Caribbean, you have an idyllic vacation ahead of you. Whether you choose to borrow a small boat from your hotel or plan to rent a fully-crewed yacht and explore for a week or two, this is a chance to move at your own pace, surrounded by sea and sky. You'll be able to enjoy beaches and coves that landlubbers can't reach and to see the islands as Columbus did hundreds of years ago. The following islands offer some of the best sailing in the Caribbean.

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  • 02 of 06

    The British Virgin Islands

    Sailing in the BVI
    Photo by kansasphoto/CC by 2.0

    Often referred to as the sailing capital of the Caribbean, the British Virgin Islands offer nearly perfect sailing conditions: consistent trade winds blowing from the northeast at 10 to 25 knots, clear water and about 60 islands and cays to explore in an area that's 32 miles long and 15 miles wide. Tortola, the largest island, is the main starting point, and many operators are available to rent bareboat craft or crewed yachts, depending on your skills and interests. More than 100 yachts take part in the BVI Spring Regatta, a three-day festival that's one of the most exciting sailing events in the Caribbean.

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  • 03 of 06

    Antigua and Barbuda

    sailboats at sunset
    Photo via Shutterstock

    Constant trade winds and dozens of little harbors to duck into make Antigua and Barbuda terrific sailing destinations. If you're yachting, good bases include English Harbour and Jolly Harbour. Antigua also hosts two major sailing events during the year: the Classic Yacht Regatta, which attracts a marvelous variety of ships including traditional island crafts, classic ketches, sloops, schooners, yawls, spirit of tradition yachts, and tall ships; and Sailing Week, a world-class regatta.

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  • 04 of 06

    St. Vincent and the Grenadines

    Salt Whistle Bay, Union Island, Grenadines
    Photo by Christian Lendl/CC by 2.0

    Sailing is the best way to explore St. Vincent and the Grenadines, where the wind comes from the northeast and blows at 10 to 25 knots. This chain consists of Bequia, Mustique, Canouan, Mayreau, Tobago Cays, Palm Island, Union Island and Petit St. Vincent. These islands are unspoiled throwbacks to a simpler past; some have no development whatsoever. Drop anchor and spend the day picnicking, sunbathing and swimming on a secluded beach, or sail to several islands, exploring them all. The main island of St. Vincent, where you can rent bareboat or fully-crewed craft from a variety of operators, is the best jumping-off point.

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  • 05 of 06

    The French West Indies

    St. Barts yachts and sailboats
    Photo by Tiarescott/CC by 2.0

    The islands that make up the French West Indies -- Guadeloupe, Martinique, St. Martin and St. Barts -- are best sailed between December and April, the dry season, when the trade winds blow at 10 to 20 knots. Fort-de-France in Martinique is one of the Caribbean's loveliest bays, and of the island's several marinas, Le Marin's Port de Plaisance is the island's biggest and best-equipped.

    If you set sail in St. Martin, a good place to start is Oyster Pond. From here, you can head to Grand Case on the north shore, then to Marigot Bay, or continue on to one of the island's best known beaches, Orient Bay. The beautiful, ritzy island of St. Barts is about a half-day sail from St. Martin, as is Anguilla, where you'll find many deserted beaches.

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  • 06 of 06

    St. Lucia

    St. Lucia sailboats
    Photo via Pixabay

    Bordered by the Atlantic on one side and the Caribbean Sea on the other, St. Lucia is an ideal site for setting sail in the Caribbean. Travelers interested in all types of sailing expeditions can charter trips out of Marigot Bay and Rodney Bay, on the western/northwestern coast of the island, respectively.