Navigating the Caribbean Regatta Season

There’s no better place for a fun week on the water than racing a sailboat in a Caribbean regatta.
Caribbean regatta
Any cruiser canventure beyond their comfort zone and join in the fun of an islands-based regatta. Laurens Morrel

The sun, the warm spray, the thrill of driving fast boats all day and then partying hard every night deep in the Caribbean—it’s an awesome trifecta. 

If you’re a cruising sailor who wants to give racing a try, there’s good news: You no longer have to fly into Antigua’s English Harbour, walk the docks, crew aboard a large schooner, and then pass out on sail bags on deck for the night. Today, there are many more options for getting in on the action during the Caribbean regatta season. 

The 2024 season began in January with the RORC Transatlantic Race. In February, there was the Caribbean Multihull Challenge, the St. Maarten Heineken Regatta and the RORC Caribbean 600. The season winds down starting in April with the BVI Spring Regatta, Antigua Classic Regatta and Antigua Sailing Week. 

If you’re on your own boat, then you can enter a cruising division using white sails (no black carbon fiber and no spinnaker). There are bareboat divisions for cruisers too. 

Don’t have your own cruising boat or bareboat? Each regatta website has a “crew board” where skippers post openings. Or do it the old-fashioned way: Walk the docks, hang out at the yacht club bar, and introduce yourself. Bring your sailing résumé with you. 

Tricked-out racing machines are available from a number of chartering outfits, usually at a higher price than cruising bareboats. Chris and Lucy Jackson run LV Yachting, a racing-boat charter agency in the UK. Chris brought Pata Negra, an IRC 46, to Antigua for a group of British sailors to charter. LV Charters also has a half-dozen retired Volvo Ocean 65s available for charter. 

Global Yacht Racing in the UK brings its Beneteau 47.7s into the Caribbean each season and offers berths for singles and couples—including sailors who are racing for the first time. 

“We take them out for a few days before the races to get them familiar with the positions and maneuvers, then it’s full-on racing,” says Andy Middleton, director of Global Yacht Racing. 

On Deck, based in English Harbour, offers a race-training program aboard a Farr 65, Spirit of Juno, and rents bunks aboard for regattas. 

Even people who are used to sailing faster typically enjoy racing charters. San Francisco-based racing skipper Bratz Schneider is among them. He chartered a Beneteau Oceanis 46 from The Moorings for a vacation with his regular racing team, and told me that they couldn’t get enough, even at a slower pace than they usually hit. “We were all having a blast,” he says. For more information about these events and all of the ones in between, check out