Sailing Tradition: A Caribbean Adventure to Prickly Pear Cays

With a deep love for the ocean and a thirst for adventure, I couldn’t resist the allure of a traditional sailing experience to Anguilla’s Prickly Pear Cays. Join me as I recount a day filled with snorkeling, delicious Caribbean cuisine, and the breathtaking beauty of the Caribbean Sea.

Setting Sail on Tradition

As a former professional surfer, I’ve always had a deep connection with the ocean, and living in the Caribbean has only strengthened that bond. So when I heard about the Traditional Sailing Adventure to Anguilla’s Prickly Pear Cays, I knew it was an experience I couldn’t pass up. The day began with a warm welcome aboard Tradition, a stunning 50-foot Carriacou sloop that exudes classic charm. The crew, Brennan, Donnelly, and Deborah, greeted us with smiles and a delightful spread of homemade blackberry muffins and fruit skewers. As we set sail, the motor was silenced, and the sails were hoisted by hand, a testament to the crew’s dedication and the authenticity of the experience.

Captain Laurie, a native Anguillan, and Captain Norman, on loan from Carriacou, expertly navigated us towards Prickly Pear. The journey was smooth, with the Caribbean breeze in our hair and the promise of adventure ahead. I couldn’t help but feel a sense of freedom and excitement, reminiscent of my days chasing waves around the world. The crew’s passion for sailing was infectious, and their hard work allowed us to relax and enjoy the ride, mimosas in hand.

Exploring Prickly Pear Cays

Upon arrival at Prickly Pear, we were greeted by a brief shower of “liquid sunshine,” but it only added to the charm of the day. Equipped with snorkel gear provided by Deborah, we dove into the crystal-clear waters to explore the vibrant marine life that calls the reef home. The underwater world was teeming with colorful fish and coral, a mesmerizing sight that reminded me of the beauty and diversity of the ocean.

After our snorkeling adventure, we indulged in a sumptuous lunch of lobster and ribs, a true Caribbean feast. The sun emerged, casting its golden glow on the pristine white sand beach, inviting us to take a leisurely stroll along the shore. The island’s natural beauty was breathtaking, with its rocky coral formations and nesting grounds for sea birds. It was a moment of pure bliss, a reminder of why I chose to make the Caribbean my home.

The Journey Back to Sandy Ground

As the afternoon sun began to dip, we reluctantly made our way back to Tradition for the return sail. Deborah’s homemade cookies awaited us, a sweet treat to accompany the chilled wine and beer. The journey back to Road Bay was filled with laughter and camaraderie, as Captain Laurie shared stories of Anguilla’s rich history and culture. His knowledge of the island and its waters was impressive, and I found myself captivated by his tales.

The scenery was nothing short of spectacular, with the “Caribbean blue” waters and the view of Sandy Island creating a picture-perfect backdrop. As we moored back in Road Bay, we were treated to a traditional Martinique rum with lime and cane sugar syrup, a fitting end to an unforgettable day. Though it was bittersweet to say goodbye to Tradition and her crew, I knew that this was an experience I would cherish forever. And as I watched the sun set over the horizon, I couldn’t help but feel grateful for the opportunity to share this adventure with my readers. Until next time, keep chasing those waves and exploring the beauty of island life.

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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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