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Anguilla sits in the balmy waters of the Caribbean Sea, but its position at the region’s northeasternmost point lends it a quirky geographical trait: there’s nothing but ocean between the island and Nova Scotia, 1,828 miles to the north. That means there’s a near-constant breeze that vacillates from a gentle breath of cool air to a stiff gale—exhilarating conditions for tennis players in the punishing heat of a West Indies court.

Tennis is what brought me to Anguilla last spring with my family, where we stayed at Malliouhana, Auberge Resorts Collection—a retro-chic, 25-acre property with candy-colored villas, three lush beaches, and two hard courts. My first few games saw classic Anguillan weather that was just hot enough to help me sweat out my daily ration of rum, but fresh enough to keep me from wilting.

My playing partner was Sunzahra Liburd Banks from the Anguilla Tennis Academy (the resort can pair interested guests of all skill levels with academy students; they can also play on the academy courts for a $10 fee). Banks, 20, had been about to leave for Savannah State University on a tennis scholarship but, thanks to the pandemic, was still honing her skills last winter on the island by playing with—and giving lessons to—the hotel’s guests. She’s one of 13 locals who, in the past few years, have received scholarships to American universities with the help of the academy.

“Coach Mitch saw my potential and told me how far I could go,” said Banks, who began playing as a five-year-old in one of the academy’s summer programs. “Coach Mitch” is Mitchelle Lake, who founded the academy on two public courts in 1996 and established its permanent home in the village of Blowing Point in 2007. It’s become an incubator for Caribbean tennis talent, with six tidy courts, an after-school program, and a constant stream of visiting coaches from abroad.

The academy is also what makes Anguilla so special for a tennis-obsessed tourist, whether you’re a beginner or, like me, an unhealthily competitive recreational player whose first order of business before any trip is typing the word tennis into the search box of various hotel websites. The academy sends coaches and hitting partners to both the Malliouhana and Four Seasons Resort & Residences Anguilla.

Hotels, in fact, are the only game in town on most Caribbean islands—both for guests and the tennis-playing employees, who are allowed a precious few hours of off-the-clock training. Mitch Lake is no exception. As a child, he would hitchhike nearly seven miles from his home to Cap Juluca, a Belmond Hotel, on the island’s southwestern tip, where he was an assistant to the head of the tennis program. It was there that Lake met a patron who wrote him letters of recommendation for a tennis scholarship in the United States. Now he’s paying it forward.

At Cap Juluca, the courts are nestled behind the sugary dunes of Maundays Bay and ringed by scarlet bougainvillea. Shawn Romney, the resort’s head of tennis, grew up playing and working at the hotel with Lake. He attended college with him, too. Now he runs the place, hires academy students, and is a role model for the island’s tennis-obsessed youth.

Against Romney, I put up what I thought was a valiant fight, keeping the set level for the first six games before he overwhelmed me with an accuracy achieved only by someone who’s spent a lifetime on that specific court.

At Caribbean resorts, workers typically drift away from tennis when they grow out of their jobs. But Romney and Lake have parlayed the relationship into a situation that’s genuinely beneficial to young locals. The hope is that many of them will lead a new generation in a regional tennis boom. As for tennis tourists like myself, Anguilla remains the undisputed ace of the Caribbean.

A version of this story first appeared in the November 2021 issue of Travel + Leisure under the headline The Game Changers


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