The #1 Rated Sailing Adventures

Come and join an adventure sailing holiday like no other. We run coastal adventure holidays in the Caribbean to full expeditions up to Svalbard in the polar north and ocean passages across the Atlantic. We also run more intensive skills builders on routes such as the Bay of Biscay. Whether you are a complete novice or a more seasoned sailor, and whether you are joining us solo or as part of a group, you can come and be a part of one of these incredible adventures.

92 Items

  • sailing the atlantic
    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 2800-mile voyage from the Canary Islands to the Caribbean. Four weeks full of adventure, training, exhilarating sailing and memories of a lifetime.

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      Join Waitlist

      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.

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      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.

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      Join Waitlist

      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

      Join Waitlist

      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.

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      Join Waitlist

      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.

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      Available

      Tuesday 04th February 2025 - Thursday 13th February 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Drone shot of yacht
    Offshore

    Caribbean Offshore 1000: Antigua to Jamaica

    11 Days from £2,399

    Embark on a truly exhilarating offshore sailing passage across the Caribbean, with 1000 miles of adventure sailing across the Caribbean Sea from Antigua to Jamaica

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      Join Waitlist

      Tuesday 18th February 2025 - Friday 28th February 2025
    • Medal icon
      Experience: Low to some
    • 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.

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      Join Waitlist

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

    Galleons & Treasure: Jamaica to Cuba

    11 Days from £2,499

    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

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      1 Place Available

      Tuesday 4th March 2025 - Friday 14th March 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas