St. Maarten is one of the Caribbean's leading sailing venues, playing host each year to the St. Maarten Heineken Regatta and offering plenty of stunning anchorages. Fully equipped marinas welcome visiting boats and rent everything from speedboats to canoes. Day trips can also be arranged for deep-sea fishing or for visits to secluded nearby islands. Every March, hundreds of participants from Europe, the United States, and the Caribbean visit St. Maarten to compete in one of the world's biggest sailing events --- the St. Maarten Heineken Regatta. The event has come to symbolize the island's prominence as a sailing venue, and St. Maarten is one of the few places in the world where the average person can sail on a world-class racing boat.

The St. Maarten 12 Metre Challenge, offered year round, gives visitors the chance to experience first-hand the thrill of America's Cup racing. Aspiring sailors serve as crew aboard the U.S. Stars and Stripes, which raced in 1987, or the Canadian contenders Canada II, True North, and True North IV, as these high-performance boats are put through their paces on a shortened America's Cup course. Previous sailing experience is not necessary, only a sense of adventure.