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Set Sail for Adventure on Anguilla

Give up your beach chair for a day and chase a sunset instead

Get a feel for Anguilla’s national sport of sailing with an evening cruising the coast onboard Tradition, a traditional West Indian sloop. You may find its love at first sight – she has that effect on people.

Greeted by Captain Laurie Gumbs at the dock in Sandy Ground, we were escorted by dinghy and introduced to Tradition, our elegant sailboat for the evening. Our faces gleamed with excitement as we arrived, the crew awaiting us on deck. Peering up, we saw a wooden, fifty-foot, West Indian sloop draped in strong canvas sails, her body a bold cardinal red.

Tradition_1Once on board we discovered it was the windiest day in Anguilla yet this year, so we were in store for an unforgettable joy ride. First order of the day was a quick safety briefing with Laurie while his partner Deborah Vos soothed our spirits with bubbly. With several island crossings and other sailing experience under my belt, my sea legs were up for the feat, although my two guests were completely new to the sport. They embraced the adventure properly, one hand reserved for the vessel and the other for champagne.

We set off, all sails up and successfully keeled over, getting as close to the wind as possible. Deckhand Brennon and his team are there at all times to make novice sailors feel comfortable, whether you want to raise the sails, pull ropes or just relax with the breeze. After a few impressive tacks, we reached Little Bay, a peaceful spot that you can revisit time after time and never tire of its serenity. As we approached we were able to spot pelicans, high above the cliffs that circle the pristine bay.

DSC_7605_WPOnce tied to the mooring, we admired the sunset and were treated to a glass of rosé and miniature tuna tartar; talk about wow factor. Next, a rich spread was laid out, including French cheeses, charcuterie, duck-stuffed crepes, deviled eggs, shrimp cocktail, bacon-wrapped chicken with banana curry sauce, and crisp bread with freshly made tomato jam. After sunset we were offered a delicious Caribbean elixir, Tí punch, made from rum, cane syrup and a solid squeeze of lime.

Captain Laurie, a born and bred Anguillan, has a strong admiration for sailing and an eloquent ability to deliver a story. You’d know him immediately for the seafaring type with his signature croakies, long hair and island-tanned skin. Aboard, he offers a wealth of knowledge about Anguilla (he’s also the owner of the famous Pumphouse restaurant).

A natural sailor, Laurie has always adored the sea, and his dream of captaining his own boat came true with the help of Deb. Originally from Canada, Deb’s passion for the outdoors inspired her to join a year-long transatlantic voyage on a classic sailing ship for her fortieth birthday, which in turn led her to meet Laurie at a sailing regatta. The rest is history. Together with their bare hands, sweat, and gusto, they brought Tradition back to life.

DSC_7674_WPOut of the many stories Laurie told over the evening, the most memorable was the tale of Tradition’s storied history. We cozied up under the stars with a bottle of Jack Iron Rum, a 160 proof Caribbean liquor, and with warm bellies and keen minds, we listened to Laurie. Tradition is originally from the small island of Carriacou, and many captains before Laurie have sailed her through every corner of the Caribbean. She was first used to smuggle loot between islands – everything from rum and cigarettes to food and even kitchen appliances. Laurie painted a picture of an old captain at the helm, peering over refrigerators stacked up high, trying to steer ahead in the darkest of the night. He explained why she was the perfect runner, “You cannot see red at night!”

Leaving Little Bay, Deb arranged cushions for us on deck so we could stare up at the sky, watching the mast sway back and forth under the moonlight. As we looked up, a fiery shooting star appeared, ending a cherished evening spent onboard Tradition.

Contact your concierge to try sailing aboard Tradition on your next trip to Anguilla.

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Lacy Colley Yamaoka