Sail & Explore: Coastal Adventures with Time Ashore

Experience the best of both worlds with our coastal sailing trips, offering shorter sailing days and ample time to explore ashore. These run in all regions of the world. Delight in the charm of seaside villages, sun-drenched beaches, and scenic trails while enjoying wonderful sailing each day. Our coastal-rated adventures are perfect for those who want the thrill of the sea and the joy of discovery on land. On coastal adventures,  every day is an opportunity to sail. explore, and discover the world. Read our full guide to coastal sailing trips here.

31 Items

  • 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
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      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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      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.

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      1 Place Available

      Tuesday 21st January 2025 - Thursday 30th January 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
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      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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      2 Places Available

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

    Antigua 5 day Explorer

    6 Days from £999

    Experience paradise with a 5 day Antigua sailing adventure. Sail in crystal-clear waters, wander sun-kissed beaches, dive on coral reefs, and discover this paradise island. 5 days of tropical bliss and unforgettable sailing.

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      Available

      March 18-23 2025
    • Medal icon
      Experience: None
  • playa sirena cuba
    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.

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      Available

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

    Antigua 5 day Explorer

    6 Days from £999

    Experience paradise with a 5 day Antigua sailing adventure. Sail in crystal-clear waters, wander sun-kissed beaches, dive on coral reefs, and discover this paradise island. 5 days of tropical bliss and unforgettable sailing.

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      Available

      March 25-30 2025
    • Medal icon
      Experience: None
  • Duart Castle
    Coastal

    5 Days Sailing The Western Isles of Scotland

    6 Days from £899

    Join this gorgeous 5-day sailing adventure around the enchanting Isle of Mull on Scotland's west coast. Explore rugged coastlines, historic castles, and beautiful anchorages. Discover wildlife, embrace nature, and enjoy superb sailing.

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      Available

      Monday 9th June 2025 - Saturday 14th June 2025
    • Medal icon
      Experience: None
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      Region: UK & Ireland