Sail, Explore and Soak Up the Sun on Idyllic Islands
Sailing in the Caribbean offers a world of adventure across its many islands, from the Windward Islands of Antigua, Dominica, and Guadeloupe to the spice-scented air of the Grenadines.
The Caribbean Sea, with its reliable and warm trade winds, crystal clear waters, and sheltered anchorages, is a sailor’s paradise. It is ideal for novice sailors eager to improve their sailing skills and explore the serene beauty of magical locations such as Dominica or the Tobago Cays. It is also loved by more experienced sailors for its great wind, wide variety, and endless opportunities to explore.
33 Items
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Offshore
Sail the Atlantic in the ARC
31 Days from £5,999
Sail across the Atlantic Ocean with Rubicon 3 in the Atlantic Rally for Cruisers (ARC), a 2800-mile voyage from the Canary Islands to the Caribbean. Four weeks full of adventure, training, exhilarating sailing and memories of a lifetime.
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Join Waitlist
Wednesday 20th November 2024 - Friday 20th December 2024 -
Experience: Low to some -
Region: Caribbean & The Americas
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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
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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 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
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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Join Waitlist
Friday 24th January 2025 - Saturday 1st February 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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Offshore
Caribbean Offshore 1000: Antigua to Jamaica
11 Days from £2,399
Embark on a truly exhilarating offshore sailing passage across the Caribbean, with 1000 miles of adventure sailing across the Caribbean Sea from Antigua to Jamaica
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Join Waitlist
Tuesday 18th February 2025 - Friday 28th February 2025 -
Experience: Low to some
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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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1 Place Available
Thursday 20th February 2025 - Saturday 1st March 2025 -
Experience: Low to some
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Region: Caribbean & The Americas
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Coastal
St Maarten Regatta
10 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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Join Waitlist
Tuesday 4th March 2025 - Thursday 13th March 2025 -
Experience: None
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Region: Caribbean & The Americas
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