Top Anguilla Sailing Tours

What could be better than sipping cocktails as the sun sets over the Caribbean Sea? This traditional sailing tour makes that dream a reality, and gives you a tour of Anguilla in a traditional wooden boat during golden hour—when the scenery looks at its most stunning. Plus, a small group limited to 12 people means you’ll enjoy an intimate atmosphere.

Board Tradition—a retired cargo sailboat that now serves as a luxurious leisure vessel—for a sail to the Prickly Pear Cays, a small group of islands off Anguilla’s coast. Enjoy snorkeling, swimming, a lobster lunch, and free time to walk white sand beaches. On the return trip, take advantage of the open bar and satisfy your sweet tooth with chocolate chip cookies and fresh watermelon.