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Another Side Of The Caribbean's Most Luxurious Island: The Les Voiles De Saint Barth Regatta

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Here’s the thing about regatta: It’s more accessible than you might think.

Here’s the other thing about regatta: It’s harder than it looks. Also, kind of scary.

Both of those truths became clear to me earlier this month, when I returned to St. Barth for the island’s less-serious regatta, Les Voiles de Saint Barth. I’d signed on to crew on an all-levels-welcome boat with Ondeck Sailing, a premier sailing company in Antigua.

I’d sailed with Ondeck before, during a “chase the race” and lesson during Antigua Race Week a couple years ago, and liked their inclusive approach. “Sailing is one of those few sports in which people of any age, sex, ability and background get thrown together and come out a tight team ,” says Kay Anthony, a co-owner of Ondeck, who was on my team in St. Barth.

Any ability is the key phrase there. Her husband, Pete Anthony, says they started Ondeck about ten years ago with a focus on encouraging new people to get into sailing—the training school offers more courses than anyone else in the Caribbean, and the regatta arm sends a boat to every race throughout the winter season, selling individual places on each to people of various skill levels. “We aim to make people feel welcomed and comfortable about learning in a fun environment.”

I put those promises to the test. When I arrived in St. Barth, my experience was limited to that “chase the race” and a three-day basic keelboat certification program last summer in the BVI. I needed help getting onto the boat, and I’d never seen a spinnaker in person. The next day, I was helping to fly one, as part of a team of eight on a 39-foot boat.

Racing, obviously, is nothing like pleasure cruising. I spent the first afternoon scared, and that was just the relatively mellow practice day. But after four days of racing, I had my sea legs. (Sort of: My main roles on the boat were sometimes fetching bottled water, sitting on a rail as ballast, and staying out of the way.) It helped that Ondeck hired top-notch professional crew. Skipper Nick Newling-Ward remained the picture of calm through the inevitable mishaps, and first mate Ebbe Strendell provided much-appreciated humor (and excellent scrambled eggs). Both were unfailingly competent, endlessly patient and reassuring, as were my other five teammates, all of whom were far more experienced than I.

Les Voiles de Saint Barth is itself a welcoming environment. There are plenty of 100-foot racing machines and a few sexy catamarans with their all-pro crews, and plenty of people who take the competition as seriously as at any other regatta. But many of the 70 boats in Les Voiles this year were smaller, and like we came to define ourselves, “serious about having fun.”

Off the water, everyone was serious about having fun. And St. Barth is serious fun to begin with. Every night’s party had pole dancers and live bands, the clubs of Gustavia were packed all week, and the main crew party, on Shell Beach about halfway through the week, saw about 1,000 people cutting loose. Thankfully it was followed by a day off, during each everyone went to Nikki Beach for an afternoon of dancing on tables and drinking jeroboams of Veuve Clicquot.

While those jeroboams went for about €1,600 (Team Ondeck did not indulge) and St. Barth will never be an affordable island, the other nice surprise from my trip was how much fun the simpler side of St. Barth turned out to be. Everyone goes to Le Select for snacks or maybe lunch (and they have for more than 60 years), but a burger or salad there turns out to be a tasty casual dinner—some say the place inspired the song “Cheeseburger in Paradise.” Eddy’s, owned by the son of Select’s owner, is slightly more dressed up, but serves great French-creole-Asian food at fair prices in a beautiful tropical garden. And the quality of the sushi (and the live soul music) at Le Bête à Z’ailes (Baz Bar) makes it worth a dinner every time I visit the island.

But my favorite meal on St. Barth was lunch the day after the races ended. I went away from the beach party scene and into the quiet, serene garden of Tamarin, out near Saline. The new-ish young owners brought a fresh energy to the place, which is still centered on a massive 100-year-old tamarind tree. A simple meal in the shade was just what I needed after a week in the sun and the sand and the salt.

Les Voiles de St. Barth will be April 12-16 next year. Ondeck’s 2016 regatta calendar is available here.