33 Items

  • Montserrat
    Coastal

    The Mystery Islands of the Caribbean

    11 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
    Quick Buy View
  • 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
    Quick Buy View
  • 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
    Quick Buy View
  • 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
    Quick Buy View
  • 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
    Quick Buy View
  • Caribbean island
    Coastal

    The Windwards Islands: Exploring the Grenadines

    12 Days from £0

    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
    Quick Buy View