I strolled along the sandy shores of Anegada as a Caribbean squall swept over the island. The rain fell heavily, yet the sudden chill was oddly refreshing. The scene around me resembled something from a travel brochure.
Another American sailor who had joined us for the Lenny Shabes Sailing Festival flotilla approached me on the deserted beach. His floppy hat shielded his face from the downpour.
As we passed each other, he grinned. “It doesn’t get better than this.”
If there were words to capture the essence of this flotilla, it would be those simple yet profound words.
Sailing has a way of making any moment perfect. On that beach in Anegada, the entire journey seemed to find its definition.
Fourteen boats, 85 guests, and numerous islands to explore—this was what the Lenny Shabes Sailing Festival was all about. It celebrated sailing while honoring the legacy of American Sailing Founder Lenny Shabes. When a group of sailors gathers, you can imagine the tales spun over rum drinks. Whether on catamaran decks or sandy beaches, we all became part of the American Sailing Family in the British Virgin Islands.
The Raft Up
Our lead captain from the American Sailing School Sailing Virgins organized a sailor’s paradise—a raft where our boats formed a floating alley off Prickly Pear. The music blared, and swimmers danced inventively in the water. The jovial antics of sailors reached their peak as the Rum Runner arrived, elevating the energy on every boat and the water itself. Grills were fired up, flotation devices tossed into the water, and the biggest open-water pool party many of us had ever seen ensued.
The Regatta
Fifteen Hobie Cats set sail to compete in the inaugural Lenny Shabes Hobie Cat Regatta. While the winner was uncertain, everyone was too engrossed in the fun to mind the outcomes. Rumor had it the PhD in Meteorology took the race, but no sailor would admit to losing. The Bitter End Yacht Club hosted the race and a bonfire party that stretched into the night. Dinner, drinks, and dancing on the beach solidified friendships that felt lifelong after racing Hobie Cats together.
The Willy T
No trip to the British Virgin Islands is complete without a visit to the Willy T. People leaped off the back, singing and dancing as the day melted away. Our day began with a floating party aboard the lead American Sailing Catamaran and ended with farewells under a full moon, accompanied by a small glow party.
The Lenny Shabes Sailing Festival in the British Virgin Islands marked the first-ever celebration of American Sailing’s founder, Lenny Shabes. At its core, the festival embodied the spirit of sailing and camaraderie among sailors. It was more than just an event; it was a gathering of our sailing family, a heartfelt tribute to the sport we cherish, and a joyous celebration of the sea.
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