Sailing Catamaran riding the waves near SXM



Widely regarded as the sailing capital of the Caribbean, St. Maarten/St. Martin offers myriad ways to set sail.


By Michele Korteweg


Whether you’re a major competitor in the St. Maarten Heineken Regatta or a novice mariner, sailing is a fun and accessible activity to all who visit St. Maarten/St. Martin. Depending on your skill (and thrill) level, your expectations, and your budget, there are lots of options to enjoy the turquoise waters surrounding the island and explore its beautiful coastline.


First off, the St. Maarten Heineken Regatta is an annual sailing event that takes place the first full weekend in March. This year, the 43rd edition will be celebrated from March 2–5, 2023. The event combines world-class racing with splendid onshore entertainment, also known as “serious fun parties.” While many people race their own boats, there are also a good number of people who charter boats in order to participate, making for all the fun and none of the worry. Race charters are becoming more popular and are a perfect means to tick off this bucket-list experience.


If you aren’t a sailor, this can still be your new favorite event, as many people flock to the island to be part of the bustling energy that is generated in the weeks surrounding the St. Maarten Heineken Regatta. Lots of people book their tickets on the spectating boats early, as they can’t wait to watch the 100-plus boats racing around the island. Watching the starts from the water is the ultimate way to enjoy this event — unless, of course, you are a big music lover. Then you would also thoroughly enjoy the activities organized at the Regatta Village at Port de Plaisance, where all the best of St. Maarten/St. Martin comes together: ice cold drinks, food, and music. There is so much going on that it’s best to visit to get all your information.


What if March is not a good time for you to visit St. Maarten/St. Martin? Or perhaps you like sailing, but a big event like the regatta is a bit overwhelming? Let’s go over some other options for you to get out on the water, feel the breeze in your hair and the salty sea spray on your face, and witness beautiful St. Maarten/St. Martin from the water. It’s an experience that is hard to beat.


For keen sailors, racers, or even those who never set foot on a boat, you can have a brilliant time on the 12 Metre Experience, which invites you to race former America’s Cup boats as actively as you please.


A big-budget item, but a vacation on its own, is a weeklong boat charter, where you can cruise the waters at your own pace. Discover quiet and gorgeous bays — like Happy Bay, Grand Case, Tintamarre, and Pinel — or even visit the surrounding islands like St. Barths and Anguilla. You can charter through Sunsail or look into private options. If you are on a budget, you can always consider picking one of many day sailing charters that bring you this joy for a fraction of the price of a full-week charter. Take your pick from sailing catamarans, monohulls, fast racing, or comfortably cruising boats. Whatever you choose, that smile will be plastered on your face for a while — even after you come back home to rain or snow.


Becoming more popular are vacations where you work on a skill. St. Maarten/St. Martin is a fantastic place to learn how to sail or to further develop your sailing skills. You can book sailing lessons in dinghies, which are smaller sailboats like Lasers and double-handed boats, at the Sint Maarten Yacht Club; or if your focus is on bigger keelboats and internationally recognized certification, the Maritime School of the West Indies offers you great options.


Whatever you choose to do, you won’t be disappointed by your time on the waters around St. Maarten/St. Martin. The trade winds offer fantastic sailing conditions, and let’s not forget the average temperature of 80 degrees Fahrenheit (27 degrees Celsius). When is the last time you tried something new? Maybe now is the time to make it happen and enjoy an unforgettable sailing experience.