• Caribbean Multihull Challenge

    Caribbean Sailing Association , Collectivity of Saint Martin

    Races will be held in the coastal waters of Dutch and French St Maarten / St Martin; and for the Ocean Class (larger and higher speed potential entrants) there will be longer races around St. Barth’s and Saba.

    $14,600
  • RORC Nelson’s Cup

    RORC Fort Charlotte, Antigua and Barbuda

    The 17th edition of the RORC Caribbean 600 will start on Monday 23rd of February, 2026. Starting and finishing in Antigua. The classic Royal Ocean Racing Club's non-stop 600nm race goes around 11 Caribbean islands.

    $3000
  • Heineken Village Regatta

    Heineken Village Regatta , Sint Maarten

    The St. Maarten Heineken Regatta will celebrate its 46th edition in 2026 from MARCH 5-8, 2026. It is the largest regatta in the Caribbean and likely the largest warm water regatta in the world.

    $3000
  • St. Thomas International Regatta

    STIR , Virgin Islands (U.S.)

    The St. Thomas International Regatta (STIR) is taking a tack towards tradition by moving the event’s date to Easter Weekend, April 3-5, 2026. This global holiday, a calendar staple for the International Rolex Regatta and now STIR for over two decades, marks an occasion when families and friends make time to gather and celebrate.

    $3000
  • Les Voiles de St. Barths

    Le Voiles de St. Barths , Saint Barthélemy

    Regularly attracting over a thousand of the greatest sailors from across the globe, the Les Voiles De Saint Barth is a fantastic regatta for charter guests to join in on.

    $200
  • RiTA

    Regattas in The Abacos is brought to life by a dedicated team of passionate volunteers who share a love for sailing and a deep commitment to showcasing the beauty of the Abacos, Bahamas. This enthusiastic group works tirelessly to organize every aspect of the event, from planning the races to coordinating the vibrant evening celebrations.

    Their goal is not only to create an unforgettable experience for participants and spectators but also to highlight the stunning waters, rich culture, and warm hospitality that make the Abacos so special. Their efforts ensure the regatta remains a cherished tradition for the sailing community and a proud celebration of this island paradise.

    $3000
  • Lobster Festival

    Anegada , Virgin Islands (British)

    Dubbed the “grandest crustacean feast in the Caribbean,” the annual Anegada’s Lobster Festival takes place November 28th – 30th. Spiny lobster is a ubiquitous delicacy in the Caribbean but on Anegada in the British Virgin Islands, local restaurants have been perfecting the preparation of the sweet crustacean, from serving it in an unpretentious manner fresh from the grill to magically transforming the prized seafood into decadent ice cream.

    $20,950