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.
61 Items
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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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Join Waitlist
Monday 23rd December 2024 - Friday 3rd January 2025 -
Experience: None -
Region: Caribbean & The Americas
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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 -
Experience: None
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Region: Caribbean & The Americas
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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 21st January 2025 - Thursday 30th January 2025 -
Experience: None
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Region: Caribbean & The Americas
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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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1 Place Available
Tuesday 04th February 2025 - Thursday 13th February 2025 -
Experience: None
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Region: Caribbean & The Americas
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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
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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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Available
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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2 Places Available
Tuesday 18th March 2025 - Friday 28th March 2025 -
Experience: Low to some
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Region: Caribbean & The Americas
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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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Join Waitlist
March 18-23 2025 -
Experience: None
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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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Join Waitlist
March 25-30 2025 -
Experience: None
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