Racing with a Smile: Caribbean Regattas for Everyone

Dive into the heart of the Caribbean Racing Season, where the thrill of competition meets the beauty of tropical sailing. Our curated selection of races includes the exhilarating Grenada Sailing Week, the challenging RORC Caribbean 600, and the iconic St. Maarten Heineken Regatta. These premier events attract sailors from around the globe, offering a unique blend of competitive racing and island-hopping camaraderie. Whether you’re a seasoned racer or looking to experience the adrenaline of sailing competition for the first time, our races provide the perfect platform to learn and develop your skills against the backdrop of the Caribbean’s turquoise blue waters and beautiful islands. Join us for an unforgettable season of speed, strategy, and celebration in some of the world’s most stunning sailing destinations. Read our full Caribbean Racing guide here.

3 Items

  • Grenada Sailing Week
    Coastal

    Grenada Sailing Week

    9 Days from £1,999

    Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.

    • Calendar icon

      1 Place Available

      Friday 24th January 2025 - Saturday 1st February 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • rorc caribbean 600
    Offshore

    RORC Caribbean 600

    10 Days from £2,499

    Race in the RORC Caribbean 600: Six hundred miles of exhilarating offshore racing, weaving through Caribbean islands.

    • Calendar icon

      1 Place Available

      Thursday 20th February 2025 - Saturday 1st March 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • st maarten regatta header
    Coastal

    St Maarten Regatta

    10 Days from £2,499

    Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.

    • Calendar icon

      Join Waitlist

      Tuesday 4th March 2025 - Thursday 13th March 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas