25 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
Grenada Sailing Week
9 Days from £1,999
Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.
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Available
Friday 23rd January 2026 - Saturday 31st February 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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Offshore
RORC Caribbean 600
10 Days from £2,499
Race in the RORC Caribbean 600: Six hundred miles of exhilarating offshore racing, weaving through Caribbean islands.
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Available
Thursday 19th February 2026 - Saturday 28th February 2026 -
Experience: Low to some
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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
St Maarten Regatta
11 Days from £2,499
Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.
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Available
Tuesday 3rd March 2026 - Friday 13th March 2026 -
Experience: None
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Region: Caribbean & The Americas
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