58 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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Available
Tuesday 23rd December 2025 - Saturday 3rd January 2026 -
Experience: None -
Region: Caribbean & The Americas
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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.
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Available
Tuesday 6th January 2026 - Thursday 15 January 2026 -
Experience: None
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Region: Caribbean & The Americas
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Coastal
The Windwards Islands: Exploring the Grenadines
10 Days from £2,299
Embark on an unforgettable adventure sailing vacation through the Windward Islands, where each island offers its unique paradise.
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Available
January 20-29 2026 -
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 £2,299
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.
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Available
Tuesday 3rd February 2026 - Thursday 12th February 2026 -
Experience: None
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Region: Caribbean & The Americas
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Coastal
The Mystery Islands of the Caribbean
10 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
Tuesday 17th February 2026 - Thursday 26th February -
Experience: None
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Region: Caribbean & The Americas
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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.
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Available
March 02-12 2026 -
Experience: None
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Region: Caribbean & The Americas
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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.
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Available
Tuesday 17th March 2026 - Thursday 26th March 2026 -
Experience: None
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Region: Caribbean & The Americas
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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.
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Available
March 31-April 11 2026 -
Experience: Low to some
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Region: Caribbean & The Americas
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Offshore
Frontier Voyage: New York to Newfoundland
17 Days from £3,999
Sail from New York to St. John’s, Newfoundland, exploring iconic stops like Newport, Nantucket, Nova Scotia’s Lunenburg and Canso, and Newfoundland’s rugged fjords and historic ports. An epic passage blending adventure and discovery.
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Available
May 06 - 22 2026 -
Experience: Low to some
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Region: Norway, Iceland & The Arctic
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