Tradition Sailing Charters is an authentic Anguilla sailing experience built around Tradition, a beautifully maintained 50-foot classic wooden West Indian sloop originally built in 1978 on the island of Carriacou, Grenada. Departing from Sandy Ground, the company offers guests a distinctive alternative to modern powerboat excursions, combining traditional sailing, Caribbean history, snorkeling, beach exploration, exceptional hospitality and breathtaking views of Anguilla’s turquoise waters.
Tradition Sailing welcomes both experienced sailors and first-time guests. The professional crew handles the sailing while inviting interested guests to participate in raising the sails, learning about the vessel and even taking the helm. Shared excursions include sailing and snorkeling adventures to Little Bay, sunset cruises along the Anguilla coastline, and full-day voyages to Prickly Pear Cays featuring snorkeling and a grilled Caribbean lobster lunch.
For celebrations, families and private groups, Tradition Sailing also offers customized private charters for up to approximately 16–18 guests. The company provides a relaxed, upscale Caribbean atmosphere with professional service, drinks, snorkeling equipment and opportunities to enjoy Anguilla from a genuinely traditional sailing vessel.
