You Gotta Regatta in the Caribbean

Race Charter on Spirit of Juno Courtesy Ondeck 6

Charles Cornett crewed on a sailing yacht one summer several decades ago in the Chesapeake Bay. He loved it. Then, work and family took priority in his life, and he set sailing aside for way too long. “I had known of the Antigua Sailing Week (ASW) regatta, and it being one of the largest such events in the world, and had long harbored a desire to participate in it,” says Cornett, who lives in Winter Park, FL.

He completed several American Sailing School (ASA) courses in 2021 and became a U.S. Sailing certified instructor in 2022. After that, Cornett vowed to be more intentional about getting out on the water.

“While visiting the Annapolis Boat Show in 2022, I came across the Antigua & Barbuda Tourism Authority booth and asked them about ASW. The representative quickly dialed Peter Anthony at Ondeck Sailing, and he explained how I could participate as a crew member. I remember thinking ‘Wow, this can really happen!’ I live in Florida, so a regatta in the Caribbean offers a relatively nearby destination and is easy to get to. That, and the beautiful landscape, crystal blue waters, and reliable wind meant that the experience would be amazing — and it was,” says Cornett, who was one of the crew aboard Ondeck Sailing’s Farr 65, Spirit of Juno, in the 2023 ASW.

The Caribbean: A Yacht-Racing Paradise

The ideal place to participate in a sailing regatta is the Caribbean, says Ian Pedersen, senior marketing manager for Clearwater, FL- headquartered The Moorings & Sunsail, which sponsors yacht charters for several Caribbean regattas. “It offers all the excitement and thrills of racing competitively while allowing you to leave the foul-weather gear at home. Incredible weather, consistent trade winds and lively beach parties to end each day are just part of what makes a Caribbean regatta so appealing.”

Competitive racing at the St Maarten Heineken Regatta ©LaurensMorel

A big help for sailors to plan which regattas to compete in is the Caribbean Sailing Association (CSA) five-year Caribbean Regatta Calendar. Creating the calendar helped CSA work with each island’s regatta organizers to ensure no overlap in dates.

“Each island adds its flavor to their regatta, which is unique to sailing events. You have the champagne, high-end experience at Les Voiles de St. Barths, the down-to-earth, community feeling at BVI Spring Regatta, lots of one-design racing in St. Thomas, and the Serious Fun in St. Maarten. The islands themselves add to the mix. There’s around the rocks racing with lots of beautiful vistas. Plus, each island has its local culinary delights, cocktail specials, accommodations and much more. You see teams pick a new regatta each year simply because they fell in love with the Caribbean and want more,” says Michele Korteweg, CSA president and director of the St. Maarten Heineken Regatta.

A typical day at ASW gives a good idea of what race days are like at Caribbean regattas.

“You get up early to get the boat prepped, pick up or make breakfasts and lunches, and get out on the water by 9:00 a.m. and ready for first warning signals,” says Alison Sly- Adams, CSA past president and ASW director. “Racing starts promptly at 10:00 a.m. and usually finishes by 2:00 p.m. ensuring boats are back on the dock at 3:00 p.m. ready for wash down and repairs. There’s an afternoon prize giving, with time for plenty of healthy banter by competitors about the racing and hobnobbing with sailing celebrities, before heading out to one of the restaurants and party venues in the harbor for a big crew night out. So, there are equal parts competitive racing and a lot of fun off the water.”

The racing itself is a combination of round-the-islands and round-the-buoy courses, both short and long depending on the type of boats in each class.

“We start with our slower paced yet competitive Sailing Festival where we feature longer course racing,” says Cayley Smit Pile, director of the BVI Spring Regatta. “For example, there’s the Nanny Cay Cup that sails around the island of Tortola. Then the traditional three-day regatta is faster paced with two-to-four or more races per day, depending on class. The beauty is that even if you’ve raced with us for years, every year is different. That’s because our professional race committee decides each morning which course they will run for each class, and where they will run it — in a protected channel or offshore and based on the conditions.”

Classes range from grand prix style with sleek sailing machines manned by a professional crew to talented weekend warriors and island racers on smaller boats, and even beginners as crew to sit on the rail for weight, affectionately called “rail meat.”

Five Ways to Join the Fun

These five ways to participate in a regatta mean there is something for everyone.

BYOB (bring your own boat)

Cruisers who come to the region for the winter can sail their “home” in cruising or jib and main classes. Professional teams piggyback their racing machine on transport vessels that sail from the eastern United States or western Europe. Global yacht transport companies include Dockwise, Sevenstar, and Peters & May. St. Thomas, U.S. Virgin Islands, Antigua and Le Marin, Martinique are destinations for yacht arrivals in the Caribbean.

Charter a boat

Chartering is likely the most popular way to race for those who don’t BYOB. The Moorings & Sunsail offer monohulls to race.

“The process is much like chartering a yacht for a normal sailing vacation; however, there is an additional cost for the regatta entry fee. We coordinate with the regatta organizers to ensure your vessel is properly entered into the regatta. Usually, there is a separate charter race class, so don’t worry, you aren’t going to be up against a professional racer in a carbon-fiber hull! The charter yacht race class is always fun, and very competitive since each yacht is outfitted similarly,” says Pedersen.

St. Thomas Sailing Center (STSC), the racing arm of the St. Thomas Yacht Club, owns a fleet of one-design IC24s it charters for the island’s annual St. Thomas International Regatta, which celebrates 50 years in 2024.

“Our IC24 charter program involves a race ready IC24 (a converted J24 with Melges24 style deck, small jib with a symmetrical spinnaker). You and your crew show up and head out sailing within a 15-minute turnaround. No launching, dealing with wind, setting up the boat, sail selection for the day, etc. Just hop on the boat and sail from the mooring field to the racecourse a quarter mile away,” says Bobby Brooks, STSC’s executive director. “This year we are also offering our Race with a Pro program. Come down with three of your crew or just as an individual and sail in a day-and-a-half clinic before the regatta. The clinic will have morning lectures, on-the-water drills, practice races, and video debriefs using the latest coaching software. Then sail in the regatta with a professional coach and racer on your boat.”

The crew spots are less expensive than chartering an entire yacht, but no less thrilling. “Race novices want to ensure they will learn, and we get people involved,” says Anthony, of Ondeck Sailing, which offers its Spirit of Juno for charter in eight Caribbean regattas. “Learn a position like helming and calling tactics, and then rotate. We have two to three of our Pro crew onboard for safety and instruction.”

Look for boats that need crew

“Crewing on a boat isn’t easy as most teams are made up in advance. So, it’s an opportunity that most of the time doesn’t become available until the last minute,” says the CSA’s Korteweg., the online scoring system used by most Caribbean regattas, has a crew/boat/charter button on each regatta’s page. Crews in search of a boat can post their skills and experience here, as well as boats that need crew.

Spectating at the St Maarten Heineken Regatta ©LaurensMorel


“ASW is known for its ‘Chase the Race’ spectator opportunities,” says Sly-Adams. “We charter 60- to 80-foot catamarans and sell spots on board daily to go out and watch the racing. This year, we are expanding to helicopter tours and VIP charters.”

Both The Moorings & Sunsail offer a range of catamarans perfect to use as spectator yachts, which allow you to follow the races and festivities but still participate in the event at your own pace.

Join regatta celebration parties

“Whether it’s a nightly affair, or a grand closing party, in the Caribbean we do like to dance with our feet in the sand to soca music! Of course, it varies from the world-renowned shows at St. Maarten Heineken Regatta to Reggae in the Park in Antigua to more intimate, local shows at the other islands,” says the CSA’s Korteweg.

Finally, you don’t have to be a sailor to attend and enjoy a Caribbean regatta. “Several of the crew on our boat brought along their spouses,” says Cornett. “There are always plenty of sightseeing opportunities on land for the non-sailors to enjoy.”

2024 International Caribbean Regatta Calendar

Grenada Sailing Week 2023 Credit Arthur Daniel

Barbados Sailing Week

January 15-22

Grenada Sailing Week

January 28-February 2

Caribbean Multihull Challenge, St. Maarten

February 1-4

St. Maarten Heineken Regatta

February 29-March 3

St. Barths Bucket Regatta

March 21-24

St. Thomas International Regatta, U.S. Virgin Islands

March 28-31

BVI Spring Regatta & Sailing Festival, British Virgin Islands

April 1-7

Les Voiles de St. Barths

April 14-20

Antigua Classic Yacht Regatta, Antigua & Barbuda

April 17-22

Antigua Sailing Week, Antigua & Barbuda

April 27-May 3

Regattas in the Abacos (RiTA)

June 23-30

Marsh Harbour, Abaco, Bahamas

Related Articles
No items found.

Want to Stay In the Loop?

Stay up to date with the latest articles, news and all things boating with a FREE subscription to Marinalife Magazine!

Thanks for subscribing!
Oops! Something went wrong while submitting the form.
Marinalife articles