Top St Maarten Sailing Tours

Sail along the coast of St. Martin during sunset on this excursion. Enjoy snacks, drinks, and entertainment as you take in the exquisite colors of a Caribbean sunset. Pick a spot on the spacious deck of the boat or upfront in the nets stretching between the two hulls of the catamaran to relax, relish the ride and watch the sun sink below the horizon, ending another beautiful day in paradise.

Adventurous outdoor-lovers will enjoy this yachting, sailing, snorkeling, and swimming experience during this 6-hour tour. We'll head to the south of the island to sail on the French and Duch sides taking a few stops for snorkeling, swiming and spotting the planes on the famous Maho Beach. Prepare yourself for a Caribbean buffet lunch and an open bar during this unforgivable experience in Sint Maarten.

End another day in tropical paradise in perfection on this sunset cruise. Hop on board your trimaran vessel late in the afternoon, just in time to set sail as the sun sinks beneath the horizon. You’ll be served snacks and drinks to enjoy as you admire the views. This is a chilled out small-group activity that’s ideal for couples.

Climb aboard the catamaran "The Phoenix" for a sail around the sights of Sint Maarten. Explore the warm Caribbean Sea with ease with the supplied water gear, for a day of swimming, snorkeling, kayaking, or relaxing. Indulge in fresh fruit, pound cake, and a freshly prepared lunch alongside refreshing cocktails, beer, and non-alcoholic beverages. Finish the day watching the planes take off as you sail past Maho Beach—a must-do when visiting the island (weather permitting).

Watch the sun set from the deck of a catamaran during this 2-hour champagne cruise from Philipsburg. Sip unlimited champagne and enjoy delectable appetizers while you sail down the coast of St Maarten towards Long Bay. Say goodbye to another day in paradise as the sun sinks below the horizon.

Sailing has sensation. Come live an unforgettable experience on a sailboat. A timeless adventure aboard our sail DE. Come hoist the sails on the Caribbean Sea and guide the boat according to the wind. Come hold the helm of the ship with the assistance of the captain! Enjoy a ship DE monohull type and enjoy DE gliding on the seas.. Experience adventure aboard a sailboat Check-out DE Fort Louis a Marigot Saint Martin Marina.

Spend a day sailing around Saint Maarten aboard a trimaran and immerse yourself in the beauty of the Caribbean. Sail along the island's south coast and up the Anguilla Channel, stopping at a bay to snorkel and swim in the pristine waters. Enjoy the beautiful scenery as you sail by and feast on lunch, snacks, and drinks on board.

Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with years of experience sailing the world’s oceans, shares captivating stories above and below the surround water. We pride ourselves on a welcoming, friendly atmosphere where you'll feel like instant friends with the crew. Enjoy homemade meals with fresh local ingredients, including a light lunch and full dinner. Swim, snorkel, and sailing. No passport required! Gratuities are not included, but all fees and taxes are covered. For special requests, contact Captain Robert directly. What makes us unique? We offer a personal, intimate experience away from the crowds, with tailored itineraries that let you explore hidden beaches and secluded spots. Your day is all about relaxation, adventure, and making memories. Let us create the perfect day on the water—your Caribbean escape awaits!

Explore the waters around St. Maarten on a 6-hour speedboat tour. Avoid the cruise ship crowds and visit both the Dutch and French sides of the island in a family friendly, small group setting, which includes five stops to see different aspects of the marine environment. You’ll swim and snorkel in a sea turtle habitat, sting rays and tropical fish on uninhabited islands. Sunbathing on some of the finest white sand beaches the Caribbean has to offer while feeling the rush of commercial jets landing directly over your head at the famous airport. Along the way, your captain will share entertaining and engaging commentary and you’ll sip drinks and indulge in unlimited snacks, all included in the price.

Watch the sunset and dine on Creole fare aboard a catamaran during this excursion from St. Maarten. Sip drinks from the open bar and munch on complimentary appetizers while the sun sinks below the horizon. Once twilight falls, enjoy a buffet-style Creole dinner, followed by dessert and Caribbean rum. Hit the dance floor to island beats while the boat sails back to the marina.

Sail to Anguilla aboard a catamaran on this full-day cruise from St. Maarten. Stop at Prickly Pear Cay to lounge in the shallows of the small island's pristine beach or snorkel among the tropical fish that inhabit the colorful coral reef. Enjoy a buffet lunch right onboard and an open bar.

Join us on Knot at Work, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy all the beauty our island has to offer in the privacy of your own group. Our attentive crew will pamper you with our on-board offer and captivate you with stories and fun facts along the way. All our day charters come with our selection of drinks and snacks, and plenty of activities for you to enjoy such as snorkeling gear, swimming noodles, paddle board and a floating mat (or should I say floating bar)!

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the luxuries for a comfortable, safe, and sustainable cruising experience. This all-inclusive sailing package is a boutique experience complete with your own captain and crew catering to your every need. It's pure luxury every step of the way. From the moment you slip off your sandals and step aboard Freedom’s sprawling teak deck, you’ll be warmly welcomed with a cool scented towel and nibble a decadent handmade chocolate as you head over to one of the luxurious lounge areas to begin a leisurely morning sail. With a sparkling mimosa in hand, you set the vibe while your experienced captain and crew take care of the rest.

On this 4-hour sail we have combined the excitement of Sailing on a great trimaran, Swimming/Snorkeling in turquoise waters of a calm bay on the west coast of St.Maarten and to top it all off the sail back to home port is during a Caribbean Sunset. On this sail there is no music other than the wind in the sails, water against the hull. On each of our experiences 16 guests is the maximum capacity.

Relax in style on this private full-day catamaran charter around St. Maarten. Climb aboard and sit back as the captain takes you on a leisurely cruise around the island. Stop at Little Bay and Tintamarre Island for snorkeling, paddleboarding, and swimming. For those who want to take it easy, simply relax on the beach. Perfect for visitors wishing to escape island crowds and enjoy the tranquility of the sea.

Enjoy comfort of slow sailing catamaran and scenic views of Sint Maarten in sunsetting light. Admire a magnificent Sun stepping down below horizon taking the light away for the ocean just to bring it back the next day on opposite side of the globe

Sail on the wind like in the old days on this morning or sunset trip on an eco-friendly sail boat with no engine. Enjoy the views as you sail between St. Martin and Tintamarre Island. You can relax on board (enjoying the complimentary snacks and open bar!) Or get a bit more active with the chance to snorkel in the sea and swim with turtles. Keep an eye out for dolphins, too.

Where golden skies meet calm seas — sunset cruising along the south side of St. Maarten on our luxury sailing catamaran, Be Happy.

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy all the beauty our island has to offer in the privacy of your own group. Our attentive crew will pamper you with our on-board offer and captivate you with stories and fun facts along the way. All our day charters come with our selection of drinks and snacks, and plenty of activities for you to enjoy such as snorkeling gear, swimming noodles, paddle board and a floating mat (or should I say floating bar)!

Where golden skies meet calm seas — sunset cruising along the south side of St. Maarten on our luxury sailing catamaran, Knot at Work.

Where golden skies meet calm seas — sunset cruising along the south side of St. Maarten on our luxury sailing catamaran, Mojito.

Where golden skies meet calm seas sunset cruising along the south side of St. Maarten on our luxury sailing catamaran, Don't Worry.

One of the luxury sail catamarans for an amazing day on the water. The Anguilla itinerary will surprise you with its white sand beaches and crystal clear blue waters; a true paradise. This itinerary is great for people who want to escape for a day and relax. Besides relaxation, you will have plenty of time to enjoy the beaches, the island offers great snorkeling and even a cliff jump for the people who dare. IMPORTANT: Please note that this itinerary is only possible in fair weather conditions. In unfavorable weather conditions, the itinerary will be automatically changed to local Sint Maarten tour. A change of itinerary is not subject to a discount or cancellation. Clearance fees are non refundable within 48 hours before departure.