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.

21 Items

  • car on cuba beach
    Coastal

    Cuba Explorer

    11 Days from £2,499

    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

      Join Waitlist

      Tuesday 18th March 2025 - Friday 28th March 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Montserrat
    Coastal

    The Mystery Islands of the Caribbean

    11 Days from £2,199

    Explore the unspoiled Caribbean on this sailing adventure to islands few sailors ever reach. Experience raw, off-the-beaten-track sailing as the Caribbean once was: untouched, adventurous, and unforgettable.

    • Calendar icon

      Join Waitlist

      March 18-28 2025
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • yacht in atlantic ocean
    Offshore

    Sail the Atlantic: USA - Bermuda - Azores - Scotland

    36 Days from £5,199

    Sail across the Atlantic Ocean on this extraordinary route from the Florida Keys, USA to the west coast of Scotland, via Bermuda and the Azores.

    • Calendar icon

      Join Waitlist

      April 04 - May 09 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • celestial navigation mid atlantic
    Offshore

    Sail Across the Atlantic Using Celestial Navigation

    36 Days from £5,599

    Once-in-a-lifetime Atlantic sailing adventure from the Caribbean to the United Kingdom, navigated by celestial navigation rather than GPS. Learn ancient techniques, sail the open ocean, and reconnect with nature on this unique adventure.

    • Calendar icon

      Join Waitlist

      Friday 04th April 2025 - Friday 09th May 2025
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • 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.

    • Calendar icon

      Available

      Wednesday 19th November 2025 - Friday 19th December 2025
    • 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

      Tuesday 23rd December 2025 - Saturday 3rd January 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Caribbean island
    Coastal

    The Windwards Islands: Exploring the Grenadines

    10 Days from £2,299

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

    • Calendar icon

      Available

      Tuesday 6th January 2026 - Thursday 15 January 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Caribbean island
    Coastal

    The Windwards Islands: Exploring the Grenadines

    10 Days from £2,299

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

    • Calendar icon

      Available

      January 20-29 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Grenada Sailing Week
    Coastal

    Grenada Sailing Week

    10 Days from £2,199

    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 23rd January 2026 - Sunday 1st February 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Antgua shirley heights
    Coastal

    The Leewards: Emerald Islands Of The Caribbean

    10 Days from £2,299

    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

      Wednesday 4th February 2026 - Friday 13th February 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Montserrat
    Coastal

    The Mystery Islands of the Caribbean

    10 Days from £2,299

    Explore the unspoiled Caribbean on this sailing adventure to islands few sailors ever reach. Experience raw, off-the-beaten-track sailing as the Caribbean once was: untouched, adventurous, and unforgettable.

    • Calendar icon

      Available

      Tuesday 17th February 2026 - Thursday 26th February
    • 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 19th February 2026 - Saturday 28th February 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Antgua shirley heights
    Coastal

    The Leewards: Emerald Islands Of The Caribbean

    11 Days from £2,299

    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

      March 02-12 2026
    • Medal icon
      Experience: None
    • 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

      Available

      Tuesday 3rd March 2026 - Friday 13th March 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Drone shot of yacht
    Offshore

    Caribbean Offshore 1000: St Lucia - Grenada - Dominican Republic

    12 Days from £2,399

    Spectacular offshore and coastal sailing in the warm Caribbean trade winds from St Lucia to the Dominican Republic, where humpback whales gather in their stunning breeding grounds - an unforgettable sailing adventure

    • Calendar icon

      Available

      March 16-27 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Montserrat
    Coastal

    The Mystery Islands of the Caribbean

    10 Days from £2,299

    Explore the unspoiled Caribbean on this sailing adventure to islands few sailors ever reach. Experience raw, off-the-beaten-track sailing as the Caribbean once was: untouched, adventurous, and unforgettable.

    • Calendar icon

      Available

      Tuesday 17th March 2026 - Thursday 26th March 2026
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas
  • Bahamas
    Offshore

    Trade Winds Trail: Dominican Republic to the Bahamas

    12 Days from £2,399

    Follow the historic routes of explorers and pirates through the Dominican Republic to the Bahamas. Discover untouched beaches, hidden cays, and dramatic coastlines on this off-the-beaten-track adventure.

    • Calendar icon

      Available

      March 31-April 11 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • celestial navigation mid atlantic
    Offshore

    Sail Across the Atlantic Using Celestial Navigation

    36 Days from £5,999

    Once-in-a-lifetime Atlantic sailing adventure from the Caribbean to the United Kingdom, navigated by celestial navigation rather than GPS. Learn ancient techniques, sail the open ocean, and reconnect with nature on this unique adventure.

    • Calendar icon

      Available

      Friday 3rd April 2026 - Friday 8th May 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • Sailing into new york
    Offshore

    Adventure 1000: Sail Bahamas to New York City

    13 Days from £2,399

    Sail 1,000 nautical miles from the Bahamas to New York City, mastering offshore skills with expert training. Experience breathtaking ocean vistas and a magical arrival into New York Harbor past the Statue of Liberty.

    • Calendar icon

      Available

      April 14-26 2026
    • Medal icon
      Experience: Low to some
    • Pin icon
      Region: Caribbean & The Americas
  • 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.

    • Calendar icon

      Available

      Wednesday 18th November 2026 - Friday 18th December 2026
    • 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 21st December 2026 - Friday 1st January 2027
    • Medal icon
      Experience: None
    • Pin icon
      Region: Caribbean & The Americas