Sint Maarten Sailing Days
A visual look at the marinas, anchorages, and island life that make Sint Maarten one of the Caribbean’s most vibrant charter destinations.
Simpson Bay Marina The heart of Sint Maarten’s yachting scene — lively, well-equipped, and the perfect starting point for a charter, with easy access to provisioning and dining.
Port de Plaisance A quieter, more sheltered marina on the island’s French side, ideal for an easy first night before heading out to explore.
Sailing Toward St. Barth A short 2-3 hour sail brings you to a completely different atmosphere — read how the two islands compare in our Sint Maarten vs. St. Barth guide.
Turquoise Anchorages Calm seas and steady trade winds make for some of the most comfortable sailing conditions in the Caribbean — especially aboard a stable, spacious crewed catamaran.
Island Nightlife & Dining From beachfront restaurants to lively bars, Sint Maarten offers a cosmopolitan energy that’s hard to find elsewhere in the Caribbean — a perfect complement to quieter days at anchor.
Planning your trip? Discover more of the best Caribbean islands to sail this winter, check the best time to charter, or explore our Sint Maarten yacht charter fleet.