31 Items
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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 -
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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Offshore
Caribbean Offshore 1000: St Lucia - Grenada - Dominican Republic
12 Days from £2,399
Spectacular offshore and coastal sailing in the warm Caribbean trade winds from St Lucia to the Dominican Republic, where humpback whales gather in their stunning breeding grounds - an unforgettable sailing adventure
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Available
March 16-27 2026 -
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 £2,299
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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