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Anguilla Regatta

The annual boat races off the coast of this tiny Caribbean island are more than a competition—they’re at the heart of its people’s identity and culture

Author James Sturz Photography Thomas Prior


This past August, Hemispheres traveled to the island of Anguilla to witness one of the most thrilling events in all of the Caribbean: the Anguilla Boat Races.

The annual competition—which takes place during the island’s week-long festivities commemorating August 1, 1834, the day that slavery was abolished in the British Empire and all of its overseas colonies—caps off the conclusion of the Anguilla regatta season, with the winning crew getting a five-figure cash prize and, more important, bragging rights. After all, this is more than a competition: It’s a tradition that dates back to 1940, with many of the participants descended from past crewmembers and also descended from the first generations of free Anguillans who, motivated by drought and famine, copied visiting New England schooners so they could sail the Caribbean in search of work on neighboring islands.

As the boat races’ origin story goes, in 1884, due to a slump in sugar prices, farmers in the Dominican Republic put a freeze on wages, which led to a shortage of available local labor. Anguillans, eager to fill the labor shortage, sailed the 450 miles west to the D.R. in convoys of crudely made schooners. The trip there was quick—a couple of days or so—but the return could take up to two weeks because of prevailing winds. Conditions were harsh—one meal a day and nowhere to sleep but on exposed decks or ballast rocks—making the rush to get home all the more intense. So, as the ships neared Anguilla, they began to race.


A far cry from the $10 million price tags on the high-tech yachts that compete in the America’s Cup, the vessels in Anguilla’s boat races can cost as little as $5,000, according to one sailor nicknamed Heavy Kasha. Boat-builder David Hodge says he built Sonic, this year’s winning craft, for a cool $28,000. Anguilla crews also come relatively cheap, with teams often comprised of friends and family. For ballast, sandbags, lead and a dozen young cousins and nephews will do. The result is a simple sloop that can reach 10 knots sailing against the wind. Downwind, it’s closer to 20.

Ericson “Eddy” Hughes (left), captain of Sonic, after sewing up Boat of the Year: “My dad was a captain, and so was my mother’s dad. As a kid, you see all the guys you know getting on boats, so of course you want to do it. Sure, there are prizes, but it’s not about the money. It’s about bragging rights.” Hughes pauses to take a look at Ross Romney, the captain of De Tree, Sonic’s main competition this season. He wants to make sure Romney’s listening before he adds, “Those bragging rights last until next Easter!” To add insult to injury, Sonic would go on to win the last race of the season, the Champion of Champions.

Forget baseball, soccer, even cricket. On Anguilla, boat racing is the No. 1 sport. On race days, the seaside cliffs along race routes are packed with spectators, cheering on their favorite vessels and their hometown crews. Some fans will even hustle around the 35-square-mile island by car to keep up with the frontrunners, while those fortunate enough to have motorboats endeavor to get an up-close look. Motorized chase boats serve two purposes: to rescue crews should their boats sink and to broadcast the action over the radio. Tony Davis, an Anguillan who resides in New York City but returns to the island every August for the races, says, “I live for this, because this is who I am.”

anguilla4THE JUMP OFF
The culmination of Anguilla’s regatta season dovetails with the island’s week-long summer festival, which comprises a number of parades and outdoor parties commemorating August 1, 1834, the day that slavery was abolished. There’s J’ouvert, the Emancipation Day Caribbean Beach Party, the Calypso Monarch Competition and the Grand Parade of Troupes. Think Carnival, Mardi Gras, Lollapalooza, the Fourth of July and Juneteenth celebrations all rolled up into one epic blowout.

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