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.
25 Items
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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 -
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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Join Waitlist
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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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
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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Join Waitlist
Tuesday 18th March 2025 - Friday 28th 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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Join Waitlist
March 18-28 2025 -
Experience: None
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Region: Caribbean & The Americas
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Offshore
Sail Across the Atlantic Using Celestial Navigation
36 Days from £5,599
Once-in-a-lifetime Atlantic sailing adventure from the Caribbean to the United Kingdom, navigated by celestial navigation rather than GPS. Learn ancient techniques, sail the open ocean, and reconnect with nature on this unique adventure.
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Join Waitlist
Friday 04th April 2025 - Friday 09th May 2025 -
Experience: Low to some
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Region: Caribbean & The Americas
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Offshore
Sail the Atlantic: USA - Bermuda - Azores - Scotland
36 Days from £5,199
Sail across the Atlantic Ocean on this extraordinary route from the Florida Keys, USA to the west coast of Scotland, via Bermuda and the Azores.
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Join Waitlist
April 04 - May 09 2025 -
Experience: Low to some
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Region: Caribbean & The Americas
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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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Available
Wednesday 19th November 2025 - Friday 19th December 2025 -
Experience: Low to some
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Region: Caribbean & The Americas
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