Setting Sail on Tradition

The Caribbean has always been my playground, a place where the ocean’s whispers guide my adventures. This time, the call came from Anguilla’s Little Bay, a hidden gem that promised an authentic sailing experience aboard the historic “Rum Runner” sloop, Tradition. As a former professional surfer, I’ve always had a deep connection with the sea, and the idea of exploring this secluded bay was irresistible.

Arriving at Sandy Ground, I was greeted by Laurie, the ship’s captain, whose warm smile and easygoing demeanor set the tone for the day. Along with a small group of fellow adventurers, we were ferried to Tradition by dinghy. The vessel, a classic West Indian Sloop built in 1978, stood as a testament to the rich maritime history of the Caribbean. Laurie shared tales of its past life as a cargo transporter, and I couldn’t help but feel a sense of awe and respect for this last surviving sail-trading vessel.

A Journey to Little Bay

As we set sail, the gentle Caribbean breeze filled the sails, and the rhythmic sound of the waves against the hull was music to my ears. Deb, Laurie’s partner, welcomed us with morning mimosas, and the camaraderie among the crew and guests was palpable. The Tradition was more than just a boat; it was a living piece of history, lovingly maintained by Laurie, Deb, and their son Noah.

The journey to Little Bay was a delightful 1.5-hour sail, with the sun casting a golden glow on the turquoise waters. I took the opportunity to learn a bit about sailing, helping the crew with the ropes and feeling the wind’s power firsthand. It was a reminder of the simple joys of life, where technology takes a backseat, and nature leads the way.

Upon reaching Little Bay, the real adventure began. The secluded cove, surrounded by magnificent cliffs, was a paradise for snorkeling and cliff diving. Equipped with complimentary snorkel gear, I dove into the warm, buoyant waters, greeted by a vibrant underwater world teeming with marine life. Turtles glided gracefully, and colorful fish darted around the coral reefs, a mesmerizing dance of nature.

A Feast for the Senses

After an exhilarating hour of exploration, it was time to indulge in a culinary delight. The crew transformed the deck into a sun-covered patio, where a feast awaited us. Lobster rolls, Greek salad, taro chips, fresh watermelon, and Deb’s famous chocolate cookies were all made from scratch, a testament to the family’s dedication to providing an unforgettable experience.

Laurie’s fresh rum punch, infused with nutmeg, was the perfect accompaniment to the meal, a refreshing blend that captured the essence of the Caribbean. As we savored the flavors, the sun began its descent, painting the sky in hues of orange and pink.

The sail back to Sandy Ground was a serene journey, with the gentle rocking of the boat lulling us into a state of blissful relaxation. The experience aboard Tradition was more than just a sailing trip; it was a journey through time, a celebration of the sea, and a reminder of the beauty that lies in simplicity.

For those seeking an authentic Caribbean adventure, sailing to Little Bay is a must. It’s a chance to connect with the ocean, embrace the island spirit, and create memories that will linger long after the journey ends.