Special Interests / Sailing and Regattas

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Caribbean Sailing & Regattas

It’s not surprising that the Caribbean’s famous love of playing and partying extends to the sea, with the warm waters and steady tradewinds of the Caribbean providing the perfect playground for an incredible number of regattas and races held throughout the islands.

Virtually every island can lay claim to some sort of sailing event during the year, even if it’s just a fun gathering for locals. However, Antigua holds the crown for its famous Sailing Week every April, one of the top events on the global racing calendar along with other notable events in St Maarten, St Thomas, St Barths and the British Virgin Islands. Some are well-established contests, which have long been a major draw on the ocean racing circuit while others are still building their reputations, having been introduced more recently.

Regattas and races held around the islands are generally open to all. While the headline competitions attract serious yachtsmen from across the world, at other home-grown events the emphasis is more on having a fun time at the beach barbecues and parties that accompany the races.

And you don’t need to own your own yacht to take part. Some companies offer yachts for charter in the races or the chance to pay for an individual place in the crew of one of vessels taking part.

For further information why not read our Yacht Charters Guide.

Top accommodation for Sailing & Regattas

Moondance,Antigua and Barbuda Villas & Villa Living

Guests will be star-struck by this offbeat hideaway with its quirky style and imaginative touches that promise a visual feast both inside and out. Sleeps 12. Read more
True Blue Bay Resort & Marina,Grenada & Carriacou Hotels & Resorts

Owner run, colourful cottages housing 44 rooms, apartments and villas on a hillside above a calm bay on Grenada’s south coast. Read more
Admiral's Quay,St Lucia Villas & Villa Living

Enjoy the best of both worlds at this development in the heart of lively Rodney Bay Marina, but tucked away in its own peaceful enclave. Sleeps 5. Read more
Amarillo,Grenada & Carriacou Villas & Villa Living

A modern 4-bedroom villa in quite grand Mediterranean and Caribbean style and with lovely views over the True Blue promontory. Read more
Biras Creek,British Virgin Islands Hotels & Resorts

A delightful retreat. Elegant and full of character, set on its own bays in the North Sound on Virgin Gorda. Just 31 very comfortable suites in cottages, excellent dining room with superb views. Stay sail holidays available on crewed yacht. Read more
Sugar Mill Hotel,British Virgin Islands Boutique/Small Hotels & Inns

One of the nicest small BVI hotels - friendly and comfortable set in pretty gardens within an old sugar estate on Tortola’s north shore. 23 bedrooms and a prize-winning dining room. Read more
Fort Recovery Beachfront Villa & Suites Hotel,British Virgin Islands Villa & Condo Resorts

A delightful cluster of 29 villa-style suites and an eight-bedroom beach house, set on a quiet beach near Tortola’s lively West End. A very low-key getaway for those seeking a relaxed setting with a therapeutic ambiance. Scuba nearby Read more