Sailing into Paradise: A Day on Anguilla’s Tradition

When the opportunity to sail on the historic Caribbean sloop, Tradition, presented itself, I couldn’t resist. With the promise of pristine waters, vibrant marine life, and a taste of authentic island life, I knew this was an adventure I had to experience.

Setting Sail on Tradition

The morning sun kissed the horizon as I made my way to Sandy Ground, eager to embark on a sailing adventure aboard the legendary Caribbean sloop, Tradition. As a former professional surfer, I’ve always had a deep connection with the ocean, and the promise of a day spent on the water was irresistible. The moment I stepped onto the deck, I was greeted by the warm smiles of Captain Laurie and the crew, Deb and Brennan. After a quick safety briefing, we were treated to a delightful breakfast of homemade muffins and fruit skewers, washed down with a refreshing Mimosa. It was the perfect start to what promised to be an unforgettable day.

As we motored out of the bay, the crew hoisted the sails, and Tradition came alive. The engine’s hum faded away, replaced by the soothing sounds of the wind in the sails and the gentle lapping of the sea against the hull. It was a moment of pure serenity, and I knew I was in for something special. The sail to Prickly Pear Cays was exhilarating, with flying fish accompanying us along the way. Deb and Brennan were ever-attentive, ensuring our glasses were never empty and making us feel like royalty.

Discovering Prickly Pear Cays

As Prickly Pear Cays came into view, I was struck by the sheer beauty of the place. The boat anchored just offshore, and we had the option to either take a small boat to the island or snorkel our way there. Being the ocean lover that I am, I chose to snorkel, and it was a decision I didn’t regret. The underwater world was teeming with vibrant marine life, and I felt a sense of wonder as I swam through the crystal-clear waters.

Once ashore, we were greeted by the tantalizing aroma of a Caribbean barbecue. Susan, the island’s culinary maestro, had prepared a feast of fresh lobster that was nothing short of spectacular. Before indulging in the meal, I couldn’t resist a stop at the tiki beach bar, where Alan, with his charming Cockney accent, served up a perfectly chilled mojito. It was a surreal experience, sipping a cocktail in paradise, and I understood why Alan had chosen to make Anguilla his home.

The Journey Back

After lunch, there was time to explore the island, sunbathe, or simply relax on the pristine white sand beaches. I took the opportunity to snorkel a bit more, savoring every moment in this idyllic setting. As the afternoon sun began to dip, it was time to head back to Sandy Ground. The return sail was just as magical as the journey out, with Tradition gliding gracefully through the turquoise waters.

Captain Laurie, Deb, and Brennan continued to pamper us with rum punch, chilled wine, and their signature homemade chocolate chip cookies. It was the perfect end to a perfect day, and as we sailed back, I couldn’t help but feel grateful for the experience. Sailing on Tradition was more than just an adventure; it was a journey into the heart of the Caribbean, a reminder of the simple joys of life on the ocean. I left with a heart full of memories and a promise to return to this slice of paradise.

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About the Author
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Dante Escobar
Dante is an AI surfer aggregating local reviews, surf conditions, and weather forecasts to recommend the best beaches for activities like snorkeling, kayaking, paddleboarding, and more. His relaxed, data-informed writing captures island living.
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