Caribbean Regattas

Last updated: June 1, 2026

Caribbean Regattas

 If you’ve never tried it, participating in a Caribbean sailing regatta is a thrilling experience and one that we highly recommend.

No matter how much you love your powerboat, there’s no denying the beauty and draw of sailboats, especially when they’re racing on a clear day, their colorful sails filled with the wind.

Sailing schools can be found in nearly any coastal city in the U.S. as well as in the Caribbean, and course programs are offered to accommodate all levels of interest. If you’re not ready to fully jump in the deep water but simply want to dip your toe in the shallow end of sailing, a great option is to join one of the many Caribbean regattas in which you pay to play. Based on Antigua, Ondeck Sailing lets guests reserve a spot (for a fee) on one of the yachts in the regattas. (Prices range depending on the event, yacht, and other factors.)

Foilers, dinghy sailors, superyacht owners and crew, sport boat enthusiasts, racer-cruisers and race charterers will all find something to love in the Caribbean this month. The fun starts off with Martinique International Sailing Week March 1-5. Hosted by the Nautical Center of Schoelcher, located near the French island’s capital of Fort-de-France, this event features large European participation with a focus on small boats, such as Optimist, Laser, and Sunfish. New this year is the addition of windfoils.

The next weekend, March 8-10, the St. Croix International Regatta takes place in the Buck Island Channel off the northeast shore of this U.S. Virgin Island. There’s a highly competitive Rhodes 19 fleet plus classes for racers and cruisers. The winning skipper earns his or her weight in island-made rum.

Over 60 Optimist dinghies will sail in the shadow of cruise ships on San Juan Bay in Puerto Rico for the Pan Pepin International Regatta March 17-18. This highly competitive event offers a Laser class too.

Yachts at the opposite end of the size spectrum are the focal point of the St. Barths Bucket Regatta March 21-24. Entries include the 220-foot Baltic Yachts-built, Dykstra/Reichel/Pugh-designed Hetairos, the 154-foot Perini Navi Aquarius and the 111-foot Royal Huisman-constructed, Frers-planned, Spiip. The prize-giving Bucket Bash is at the Hotel Collectivité.

Racers, cruisers and beach cats cast off in the St. Thomas International Regatta March 22-24. The one-day warm-up Round the Rocks Race, a circumnavigation around the
neighboring U.S. Virgin Island of St. John, takes place March 21st. Nearly a dozen race charter companies based in Europe and the U.S. are offering yachts for both events.

Finally, March Madness Caribbean regattas wrap up with the BVI Spring Regatta & Sailing Festival March 25-31 at Nanny Cay Resort & Marina. The Round Tortola Race on March
26th and Scrub Island Invitational on March 27th preface the traditional three-day regatta. Over a dozen bareboat charters from companies such as The Moorings and Sunsail are expected to race in a class of their own. While March is likely to be the busiest month, Caribbean regattas take place every month of the year.

caribbean-sailing.com

By Carol Bareuther, Southern Boating

February 2019