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  • Three Sheets Regatta

    Three Sheets Regatta

    St. Thomas, USVI , Virgin Islands (U.S.)

    A three-island regatta linking St. Thomas, St. John and St. Croix.

  • Les Voiles de St Barth Richard Mille

    Les Voiles de St Barth Richard Mille

    St. Barthélemy , Saint Barthélemy

    A week of high-level racing around St. Barth for maxis, racers and performance cruisers.

  • Antigua Classic Yacht Regatta

    Antigua Classic Yacht Regatta

    Antigua , Antigua and Barbuda

    Classic and traditional yachts race off Antigua's south coast, with the Parade of Classics in Falmouth Harbour.

  • Antigua Sailing Week

    Antigua Sailing Week

    Antigua , Antigua and Barbuda

    The grand finale of the Caribbean season: five days of racing from Falmouth Harbour with nightly prize-givings, food and concerts.

  • West Indies Regatta Festival

    West Indies Regatta Festival

    St. Barthélemy , Saint Barthélemy

    Traditional Caribbean wooden boats race and trade in Gustavia, with a craft market, food, concerts and a family day.

  • Petite Martinique Whitsuntide Regatta

    Petite Martinique Whitsuntide Regatta

    Petite Martinique, Grenada , Grenada

    Traditional boat racing and community festival on Petite Martinique over the Whitsun weekend. Dates provisional (Whitsun 2027).

  • Carriacou Regatta Festival

    Carriacou Regatta Festival

    Carriacou, Grenada , Grenada

    The Grenadines' oldest regatta: traditional work-boat and sloop racing from Hillsborough, with beach games and music. Dates provisional (expected July 30–Aug. 2).

  • Anguilla Summer Festival

    Anguilla Summer Festival

    Anguilla

    Anguilla's carnival and August Monday boat race — the anchor date is August 2; the full programme is still to be announced.