Some islands seem made for the romance of sailing and the adventure of exploring the sea. And now, when you visit Covecastles^THC on the island of Anguilla, you can sail aboard a traditionally designed, 50-foot wooden Carriacou sloop named—appropriately— Tradition.

Built entirely by hand in the British West Indies in 1978, this gaff-rigged vessel is now based in Anguilla, and is one of the few hand-built wooden boats still sailing in the Caribbean. Operated by Tradition Sailing Charters, the 12-passenger sloop with a crew of three will whisk you away for adventures that include its scheduled, four-times-a-week Tropical Cay Lunch Cruise; its Little Bay Half-Day Sail, scheduled two days a week; its evening Champagne Cocktail Sunset Sail, offered four days a week; and private chartered Romance Escape sailings.