Inside Anguilla’s Fierce and Beautiful Tradition of Boat Racing

“There are no yacht clubs in Anguilla, no commodores and flag officers in dress white trousers and blue blazers, no ensigns, no flags, no cedar paneled halls shelved with glittering trophies of past racing glories and broken records. Yet within this island, lapped by the crystal blue-green waters of the Caribbean, lurks a fever for boat racing.” — David Carty, author of the 1998-published Nuttin Bafflin and the 2011 documentary of the same name, which is available on YouTube.

Boat racing is the national sporting passion and pastime in Anguilla. In this case, boats are hand-built vessels crafted by family and friends in island backyards and neighborhoods, with 28-foot-long hulls, 54-foot-tall masts, and a 42-foot boom. These are Class A boats, with up to 20 to 22 crew. There’s also a Class B that’s 23-foot long. 

Neither has a deck, a defining feature of an Anguillan race boat. There’s only a one-foot-wide rail for seating, rocks or sandbags for ballast, and huge wing-like sails. It’s a design that is centuries in the making and creates fast and agile craft in the wind and waves.

Sailing into the Present from the Past
Anguilla’s boat racing boats were born out of defense and vocational necessity rather than recreation. Three notable events set the scene for seafaring craft to become a vibrant part of Anguilla’s history and culture. First, in 1796, at the time of the Napoleonic Wars, French warships nearly destroyed Anguilla. The governor sent one fast sailing boat to St. Kitts to fetch a British naval frigate for help in what became the successful Battle for Anguilla, which the crew did despite having to tie ballast rock on the end of the boom to counterbalance a cracked mast from falling. 

Secondly, during the mid-to-late 1800s, Nova Scotia and New England schooners started trade routes to Anguilla for salt and Sombrero Island, 34 miles north of Anguilla, for phosphate-rich seabird guano. A secondary technology transfer during this trade led Anguillans to construct their own sloops and schooners. A ship’s registry at the end of the 19th century showed a small fleet that ranged from 40 to 90 tons. Third, the turn of the 20th century saw the Dominican Republic grow rapidly with U.S. occupation and increased the need for laborers in the Spanish island’s sugar production. With a recruiting office nearby in Marigot, St. Martin, the Anguillan schooners started ferrying men west for a cane-cutting season. 

“There’s a run off the wind directly from Marigot west to La Romana and San Pedro de Macoris,” says author David Carty, who also owns Rebel Marine Ltd., on North Hill, Anguilla. “The return trip is a beat straight back to the east where the schooners would have to tack because they’re coming back into the prevailing wind. On August Monday boat races each year, we still do it. We run off from Sandy Ground, go down a couple of miles, around a boat, back into sandy ground. That is a direct consequence of the Santa Domingo pattern of sailing.”

The 60- to 70-foot schooners’ return of 100 to 150 men home to their families in Anguilla was a joyous occasion. So much so that there were tremendous bragging rights for the first and fastest boat back. Thus, the seeds of racing were sown, with these farmers and cane cutters becoming skillfully adept at sailing. Going fast was also key for smaller boats, 18- to 24-foot ancestors of today’s racing boats, fished by day. At night, they plied the waters between Anguilla and St. Martin and St. Barth’s to smuggle in spirits and evade detection by Anguillan revenue officers ready to tax them to the tilt. Rum, gin, and brandy played a big role in ‘jollification,’ a tradition where neighbors helped each other plant subsistence crops and celebrated ‘payment’ in food and drink. 

Today’s Boats & Boat Racing
Wood, cut from local white cedar trees, was used for boat building during the smuggling days. Today, island builders purchase sheets of marine plywood and shape the frames into sleek, yacht-like vessels. These craft are still planked by white pine, but instead of only nails, they are attached with epoxy resins. The exterior of the boats is covered with thin fiberglass and brightly painted with Awlgrip. The only significant upgrade has been swapping stainless steel wire for rope shrouds, which happened at the turn of the 21st century, and using professionally made carbon fiber versus hand-sewn canvas sails.

“The biggest and most popular race used to be August Monday,” says Carty. “Now, racing starts in early March, and Easter Monday is a major race. May 1, Labor Day, is another big race as is Anguilla Day on May 30. The Anguilla Day race is around the island. The last race is in August, then we pull the boats out for hurricane season.”

According to the Anguilla Boat Racing Association, 17 races are on the calendar for 2025.

Sandy Ground is the most frequent venue for boat racing, along with Meads Bay and Island Harbor. Race starts take place from the beach. 

“It’s chaotic,” says Carty. “The boats are nose to the beach, and lines are attached to the stern. All the fans on the beach have one end of the line, and the crew on the boats have the other. Then, the boats are pushed around so that the stern is hauled in and the bow is pushed out, so the sails get filled with air and the boats get active. Then, they fire an air horn, you loosen the rope, and off they go. It’s not on your mark, get set, go. If a boat has a more efficient crew and gets turned around a little bit faster, it gets a little bit of an edge. But it never really amounts to a hill of beans because I’ve seen boats that have started way behind everybody else still beat all the rest of them.”

A typical course is set off the wind. Boats sail for 3 to 4 miles, go around a market, and beat back to the beach. Nowadays, one or two races are multi-point to bring the boats closer to the beaches and let the spectators see them a little closer. The end of the season’s Champion of Champions title is based on points.

“There are rules,” says Carty. “They are not the extent as you would have in an American tradition, and I hope we don’t ever get to that. What we do have is a very controversial rule, and I don’t think anywhere else in the Caribbean has it. It’s the hard lee rule.”

He explains, “A hard lee is when the tacks of two boats are on course for a collision. The crew must shout to one another, ‘hard lee, hard lee.’ That is when captains must push their tillers hard down the lee side, which turns the boats away from each other. It’s wonderfully exciting. I think it’s something that we should never give up. It is dangerous, but it is a beautiful thing to watch.”

Carty says the Government of Anguilla is considering formally legislating boat racing as the island’s national sport. “I think that’ll be done in the next couple of years for sure,” he says.

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