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.
55 Items
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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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Join Waitlist
Tuesday 4th March 2025 - Friday 14th March 2025 -
Experience: Low to some -
Region: Caribbean & The Americas
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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.
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Join Waitlist
March 18-28 2025 -
Experience: None
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Region: Caribbean & The Americas
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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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Join Waitlist
Tuesday 18th March 2025 - Friday 28th March 2025 -
Experience: Low to some
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Region: Caribbean & The Americas
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Coastal
Trolls, Giants & Elves: Scotland & the Faroe Islands
12 Days from £2,299
True adventure sailing between the west coast of Scotland the Faroe Islands. An unforgettable journey through breathtaking landscapes.
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Available
Monday 9th June 2025 - Friday 20th June 2025 -
Experience: None
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Region: Europe & the Baltic
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Masterclass
England-Scotland: Passage Making Masterclass
12 Days from £2,199
Join an intensive sailing course from England to Scotland, focusing on more advanced navigation, seamanship, and handling challenging offshore conditions.
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Available
June 09-20 2025 -
Experience: Day Skipper +
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Region: UK & Ireland
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Coastal
Scotland’s Mystical Isles: A Hebridean Sailing Adventure
6 Days from £899
Join this short but stunning sailing adventure exploring Scotland’s wild west coast. Sail through the breathtaking Hebrides, discovering remote islands, dramatic coastlines, and historic anchorages. Experience incredible wildlife, unspoiled nature, and exhilarating sailing in one of the most beautiful regions of the world.
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Join Waitlist
Monday 9th June 2025 - Saturday 14th June 2025 -
Experience: None
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Region: UK & Ireland
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Coastal
Scotland’s Mystical Isles: A Hebridean Sailing Adventure
6 Days from £899
Join this short but stunning sailing adventure exploring Scotland’s wild west coast. Sail through the breathtaking Hebrides, discovering remote islands, dramatic coastlines, and historic anchorages. Experience incredible wildlife, unspoiled nature, and exhilarating sailing in one of the most beautiful regions of the world.
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Join Waitlist
Monday 16th June 2025 - Saturday 21st June 2025 -
Experience: None
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Region: UK & Ireland
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Coastal
Devon’s Coastal Gems: 5 Days of England’s South Coast Riviera
5 Days from £899
This 5-day Devon sailing itinerary explores Plymouth, Salcombe, Dartmouth, and Brixham, showcasing the region's rich maritime history, picturesque towns, and stunning coastline.
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Available
June 23-27 2025 -
Experience: None
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Region: UK & Ireland
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Coastal
The Wild North: Scotland to Norway
12 Days from £2,299
Sail and explore the Wild Islands of Scotland and Norway, including the Outer Hebrides, Orkney, Fair Isle and Shetland. Rugged beauty and magical wildlife.
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Available
Monday June 23 2025 - Friday July 04 2025 -
Experience: Low to some
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Region: Norway, Iceland & The Arctic
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