Sailing into History: A Day on Anguilla’s Last Caribbean Sloop

Drawn by the allure of sailing on the last surviving Caribbean sloop, I embarked on a journey to Anguilla’s Prickly Pear Cays. Join me as I recount a day filled with history, adventure, and the warm embrace of island hospitality.

Setting Sail on Tradition

The sun was just beginning to rise over Sandy Ground as I made my way to the dock, the salty breeze already promising a day of adventure. I had heard whispers of the Traditional Sailing Adventure and its legendary status among locals and travelers alike. As a former professional surfer, I’ve spent countless hours on the water, but the allure of sailing on the last surviving Caribbean sloop of its kind was irresistible.

Upon boarding, I was greeted by the warm smiles of Captain Laurie and the crew, including the delightful Deb, who immediately offered a mimosa with freshly squeezed orange juice. The vessel, aptly named Tradition, exuded a sense of history and charm, and it was clear that the crew cherished her deeply. As we set sail, the captain regaled us with tales of Tradition’s past life as a sail-trader and rum smuggler, setting the tone for a day steeped in Caribbean lore.

Discovering Prickly Pear Cays

The journey to Prickly Pear Cays was nothing short of magical. The wind filled the sails, and the ocean stretched out before us, a vast expanse of blue. Alongside a young honeymooning couple and a seasoned regular, I found myself lost in conversation with the crew, who shared stories of their adventures and the rich history of the islands.

Upon arrival at Prickly Pear, the crew’s hospitality continued to shine. Alan, our host on the island, welcomed us with open arms, and his wife Susan prepared a mouthwatering lobster lunch that was the perfect complement to the idyllic setting. With snorkel gear and swim noodles at the ready, I dove into the crystal-clear waters, exploring the vibrant reef teeming with marine life. The beach was a paradise, and I couldn’t resist the urge to simply float and soak in the sun.

The Exhilarating Return

As the afternoon sun began its descent, we reluctantly prepared to leave Prickly Pear. The sail back to Sandy Ground was an exhilarating experience, with the wind picking up and the crew expertly maneuvering Tradition through the waves. Watching them work in harmony was a sight to behold, and I couldn’t help but feel a deep appreciation for their skill and passion.

Back at Sandy Ground, none of us were eager to disembark. The camaraderie that had formed over the day was palpable, and Captain Laurie and the crew indulged us with more laughter, stories, and, of course, cocktails. It was a day that encapsulated the essence of Caribbean life—relaxed, joyful, and full of adventure. As I stepped off the boat, I knew this was an experience I’d carry with me, a reminder of the beauty and spirit of the islands.

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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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