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.
21 Items
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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 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 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 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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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
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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
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
10 Days from £2,199
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 - Sunday 1st 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
Wednesday 4th February 2026 - Friday 13th 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 £2,299
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 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
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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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
10 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
Sail Across the Atlantic Using Celestial Navigation
36 Days from £5,999
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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Available
Friday 3rd April 2026 - Friday 8th May 2026 -
Experience: Low to some
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Region: Caribbean & The Americas
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Offshore
Adventure 1000: Sail Bahamas to New York City
13 Days from £2,399
Sail 1,000 nautical miles from the Bahamas to New York City, mastering offshore skills with expert training. Experience breathtaking ocean vistas and a magical arrival into New York Harbor past the Statue of Liberty.
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Available
April 14-26 2026 -
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 18th November 2026 - Friday 18th December 2026 -
Experience: Low to some
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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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Available
Monday 21st December 2026 - Friday 1st January 2027 -
Experience: None
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Region: Caribbean & The Americas
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