Discover Your Inner Sailor in St. Maarten

If you love the sounds of sails snapping in the tropical breeze, St. Maarten stands out with two iconic ways to discover your inner sailor: the largest regatta in the Caribbean, and the year-round, hands-on 12-Metre Challenge racing experience even landlubbers can win – and which has been voted the #1 shore excursion in the Caribbean for 15 years!

At just 37 square miles, St. Maarten is the smallest island in the world to be shared by two nations – The French northern part, which is St. Martin, and the Dutch Southern part, which is St. Maarten – creating a destination with European charm and Caribbean flair. 37 beaches mean there’s always water nearby – and it’s one of the sailing capitals of the world.

Annual Regatta: “Serious Fun”

Sailors and spectators come from around the world to St. Maarten’s annual regatta (pictured below). It’s not only the biggest in the region, but it’s also among the world’s leading warm-water races, with a fleet of international competitors that provide fierce competition. 2026 marks the 46th St. Maarten Heineken Regatta, and takes place March 5 - 8, 2026.

Over 20,000 visitors gather every year on the island. In addition to recreational sailors and live-aboard cruisers, Olympic medalists, world champions, and charter crews from more than 37 countries join the exciting mix.

Racing takes place across multiple classes: Maxis, Performance Multihulls, monohulls, non-spinnaker cruising boats, bareboats, and the relaxed Island Time class. Courses mix windward-leeward and coastal races, giving competitive classes a chance to tackle up to eight races over four days while cruisers enjoy scenic, less demanding routes.

Participation is open to all – in addition to registering a team of their own, enthusiasts can charter a boat to race locally or even join an existing crew.

Is spectating more your speed? Get close to the action aboard the Official Spectator Boat, which even serves breakfast, lunch, and an open bar!

Often described as “Serious Fun,” the regatta is as much about the shared sailing and shore experience as it is about the competition. While the on-water competition delivers fast, exciting sailing by day, the energy continues each evening at the regatta village in Simpson Bay Lagoon. Open to sailors and non-sailors alike, the Village is the heart of the event’s shoreside festivities, featuring live music, prizes, local and international cuisine, and a lively Caribbean atmosphere with regional and international artists.

12-Metre Challenge: Year-Round Sailboat Racing Even for Amateurs

Even if you miss the island’s once-a-year regatta, and you’ve never been on a sailboat before in your life! You can step – or sail – directly into sailing and sporting history on St. Maarten’s 12-Metre Challenge (pictured, top) any time of the year.

This is not a sailing lesson or a relaxing cruise—it’s an all-hands-on-deck race aboard authentic 12-Metre yachts, the sleek, powerful vessels that once defined the golden era of the America’s Cup racing series.

Participants are divided between 12-Metre yachts and assigned a crew task in a friendly but exhilarating race. Professional skippers and crew handle navigation and safety, while participants get into action—grinding winches, trimming sails, and responding to the captain’s commands as the boats race against each other on a course on St. Maarten’s turquoise Caribbean water.

By the end of the race, no matter whether you’ve crewed the winning or losing America’s Cup yacht in the 12-Metre Challenge, you’ve actually participated in an authentic, thrilling and once-in-a-lifetime yacht race. And you leave St. Maarten with hard-to-beat bragging rights. You can tell all your friends, “I raced an America’s Cup yacht.”