Sail, Explore and Soak Up the Sun on Idyllic Islands

Sailing in the Caribbean offers a world of adventure across its many islands, from the Windward Islands of Antigua, Dominica, and Guadeloupe to the spice-scented air of the Grenadines.

The Caribbean Sea, with its reliable and warm trade winds, crystal clear waters, and sheltered anchorages, is a sailor’s paradise. It is ideal for novice sailors eager to improve their sailing skills and explore the serene beauty of magical locations such as Dominica or the Tobago Cays. It is also loved by more experienced sailors for its great wind, wide variety, and endless opportunities to explore.

Read our full guide on the Caribbean here.

16 Items

  • Sailing into new york
    Offshore

    Offshore Sailing from the Bahamas to New York City

    17 Days from £2,899

    Crew on an epic voyage from the Bahamas to New York City, USA, a 950-nautical-mile offshore adventure. Witness stunning sunrises, try celestial navigation, and immerse yourself in the thrill of offshore sailing.

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      Join Waitlist

      Monday 20th May 2024 - Wednesday 5th June 2024
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • yacht in atlantic ocean
    Offshore

    Sail the Atlantic: New York - Newfoundland - UK

    42 Days from £4,999

    The ultimate Atlantic sailing adventure, starting in New York City and sailing north Nova Scotia and on to Newfoundland, before crossing the Atlantic Ocean and arriving into the beautiful west coast of Scotland.

    • Calendar icon

      Join Waitlist

      Monday 15th June 2024 - Friday 26th July 2024
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • sailing the atlantic in the arc
    Offshore

    Sail the Atlantic in the ARC

    31 Days from £5,999

    Sail across the Atlantic Ocean with Rubicon 3 in the Atlantic Rally for Cruisers (ARC), a 2200-mile voyage from the Canary Islands to the Caribbean. Four weeks full of adventure, training, exhilarating sailing and memories of a lifetime.

    • Calendar icon

      Available

      Wednesday 20th November 2024 - Friday 20th December 2024
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Caribbean island
    Coastal

    The Windwards Islands: Exploring the Grenadines

    12 Days from £2,499

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

    • Calendar icon

      Available

      Monday 23rd December 2024 - Friday 3rd January 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Caribbean island
    Coastal

    The Windwards Islands: Exploring the Grenadines

    10 Days from £2,199

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

    • Calendar icon

      Available

      Tuesday 07th January 2025 - Thursday 16th January 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Caribbean island
    Coastal

    The Windwards Islands: Exploring the Grenadines

    10 Days from £2,199

    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 £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

      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 £2,199

    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

    10 Days from £2,199

    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