20 Items

  • Caribbean island
    Coastal

    The Windwards Islands: Exploring the Grenadines

    10 Days from £2,699

    Embark on an unforgettable adventure sailing vacation through the Windward Islands, where each island offers its unique paradise.

    • Calendar icon

      Available

      Tuesday 21st January 2025 - Thursday 30th January 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Grenada Sailing Week
    Coastal

    Grenada Sailing Week

    9 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

      Available

      Friday 24th January 2025 - Saturday 1st February 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Antgua shirley heights
    Coastal

    The Leewards: Emerald Islands Of The Caribbean

    10 Days from £2,699

    You can anchor under the insta-famous Piton of St Lucia, enjoy the fusion of French and Caribbean culture in Martinique, explore the Indian river and jungles of Dominica, wander the magical beaches and islands of Guadeloupe and enjoy all the energy and beauty that comes with Antigua.

    • Calendar icon

      Available

      Tuesday 04th February 2025 - Thursday 13th February 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Antgua shirley heights
    Coastal

    The Leewards: Emerald Islands Of The Caribbean

    6 Days from £2,699

    You can anchor under the insta-famous Piton of St Lucia, enjoy the fusion of French and Caribbean culture in Martinique, explore the Indian river and jungles of Dominica, wander the magical beaches and islands of Guadeloupe and enjoy all the energy and beauty that comes with Antigua.

    • Calendar icon

      Available

      Tuesday 18th February 2025 - Thursday 27th 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

      Available

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

    Caribbean Offshore 1000: Antigua to the Bahamas

    12 Days from £2,399

    Embark on a truly exhilarating offshore sailing passage across the Caribbean, with 1000 miles of adventure sailing from Antigua to the Bahamas with coastal cruising included

    • Calendar icon

      Available

      Monday 03rd March 2025 - Friday 14th 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
  • car on cuba beach
    Coastal

    Galleons & Treasure: Jamaica to Cuba

    12 Days from £2,799

    True off the beaten track sailing adventure, as we sail from the north coast of Jamaica to Cuba and explore its magical south western coast

    • Calendar icon

      Available

      Monday 17th March 2025 - Friday 28th March 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • playa sirena cuba
    Coastal

    Cuba Explorer

    12 Days from £2,799

    Adventure sailing in Cuba, with an intoxicating passage from Cienfuegos to Havana. Islands, culture, wildlife and history combined with warm, trade wind sailing.

    • Calendar icon

      Available

      Monday 31st March 2025 - Friday 11th April 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas