Racing with a Smile: Caribbean Regattas for Everyone
Dive into the heart of the Caribbean Racing Season, where the thrill of competition meets the beauty of tropical sailing. Our curated selection of races includes the exhilarating Grenada Sailing Week, the challenging RORC Caribbean 600, and the iconic St. Maarten Heineken Regatta. These premier events attract sailors from around the globe, offering a unique blend of competitive racing and island-hopping camaraderie. Whether you’re a seasoned racer or looking to experience the adrenaline of sailing competition for the first time, our races provide the perfect platform to learn and develop your skills against the backdrop of the Caribbean’s turquoise blue waters and beautiful islands. Join us for an unforgettable season of speed, strategy, and celebration in some of the world’s most stunning sailing destinations. Read our full Caribbean Racing guide here.
5 Items
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Coastal
Grenada Race Week
9 Days from £1,899
Grenada Sailing Week is the perfect first yacht race. Sail south through the Grenadines with expert training, then race by day around world famous Grenada and Carriacou, with warm trade winds, turquoise seas and spectacular island scenery all around you. There is time ashore to explore, swim and enjoy the beaches and local atmosphere, before heading back out for more racing. No previous racing experience is needed, and the whole trip is designed to get you fully involved. Final year 2027 - don't miss out!
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Available
Friday 29th January 2027 - Sunday 06th February 2027 -
Experience: None -
Region: Caribbean & The Americas
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Offshore
RORC Caribbean 600
9 Days from £2,699
Race in the RORC Caribbean 600: Six hundred miles of exhilarating offshore racing, weaving through Caribbean islands.
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Join Waitlist
Friday 19th February 2027 - Saturday 27th February 2027 -
Experience: Low to some
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Region: Caribbean & The Americas
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Coastal
St Maarten Regatta
10 Days from £2,649
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 2nd March 2027 - Thursday 11th March 2027 -
Experience: None
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Region: Caribbean & The Americas
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Offshore
RORC Caribbean 600
9 Days from £2,699
Race in the RORC Caribbean 600: Six hundred miles of exhilarating offshore racing, weaving through Caribbean islands.
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Available
Friday 18th February 2028 - Saturday 26th February 2028 -
Experience: Low to some
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Region: Caribbean & The Americas
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Coastal
St Maarten Regatta
11 Days from £2,649
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 29th February 2028 - Friday 10th March 2028 -
Experience: None
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Region: Caribbean & The Americas
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