Under sail · ST MAARTEN SAILING TOURS

Sailing in St Maarten: the 5 Best Trips

5 sailing trips  ·  seats from $133 each

Sunset runs, swim stops and full days at anchor. These 5 are the sails in St Maarten worth the booking, compared on the details that matter once you are aboard.

The Best Catamaran Day Sail in St Maarten - Little Bay offers another chance to snorkel and swim
Catamaran Sailing Trips, Sailing Tours, St Maarten Sailing Tours, Tour Reviews

The Best Catamaran Day Sail in St Maarten

1.The Best Catamaran Day Sail in St Maarten

★★★★★★★★★★5.0 · 1,552 reviews · from $139Top of the fleet

Sail from Simpson Bay aboard the family-friendly Random Wind catamaran with Captain Scott, Anne or Anna, and Jackie. You’ll visit Mullet Bay and Little Bay, snorkel, paddleboard, swing into the Caribbean, and enjoy grilled chicken, rice, salad, bread, snacks, and an included open bar. The group is limited to 30 people.

“Myself and my family had the most amazing time on the catamaran with this crew! The drinks kept flowing the entire time, the lunch was incredible, and the spots we stopped were awesome. The Tarzan swing in Mullet Bay was a cherry on top. I couldn’t recommend Random Wind and their crew any more highly. All around a fun and relaxing boat trip while on Sint Maarten”

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5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix - Maho Beach is a short but memorable pass
Catamaran Sailing Trips, Sailing Tours, St Maarten Sailing Tours, Tour Reviews

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

2.5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

★★★★★★★★★★5.0 · 904 reviews · from $139

Spend five hours aboard The Phoenix with Captain Benji and crew, sailing from Bobby’s Marina to Little Bay, Maho Beach, and Mullet Bay. Expect snorkeling gear, paddleboards, a floating mat, fresh snacks, cooked lunch, cocktails, beer, and soft drinks. The boat holds up to 36 people, with room to swim, relax, and watch planes cross Maho Beach.

“The service was amazing! They were so nice and always offering us food and drinks! Food was great. Experience was a lot of fun, with amazing views of Saint Martin!”

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Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten - Long Bay: your first chance to snorkel
Catamaran Sailing Trips, Full-Day, Private Sailing Charters, Sailing Tours, St Maarten Sailing Tours, Tour Reviews

Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

3.Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

★★★★★★★★★★5.0 · 402 reviews

Spend seven hours aboard a private catamaran with Captain Mike and host Elmira, cruising St. Maarten’s coast, snorkeling at Long Bay and Little Bay, and stopping near Tintamarre when weather allows. Coffee, snacks, BBQ lunch, snorkeling gear, paddleboarding, and an open bar are included. Bring towels and non-spray sunscreen.

“Mike and Elmira were down to earth amazing hosts who made us feel welcome from the start. They were very attentive from beginning to end making sure everyone was well taken care of. The food was homemade and delicious. They both Read more”

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Tropical Catamaran Snorkeling & Sailing - Sailing the leeward coast between stops
Catamaran Sailing Trips, Sailing and Snorkeling Trips, Sailing Tours, St Maarten Sailing Tours, Tour Reviews

Tropical Catamaran Snorkeling & Sailing

4.Tropical Catamaran Snorkeling & Sailing

★★★★★★★★★★5.0 · 353 reviews · from $132Lowest fare aboard

Spend six hours aboard a spacious catamaran from Bobby’s Marina with Captain Josh, JP, Charlie, Fritz, or another Eagle Tours crew. Snorkel at Little Bay, swim near island beaches, watch planes at Maho Beach when conditions allow, and enjoy barbecue lunch, snacks, and an open bar. Bring towels and cash for a tip.

“Our group size was 4. When we arrived for our time slot it was a great day for this trip. We boarded the catamaran and set out on the trip of a lifetime. The crew was attentive from the start to finish. The snacks, drinks and lunch were very tasteful. The snorkel stops were exciting. Nice clear blue water.”

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Tropical Catamaran Snorkeling, Sailing And Beach Experience - Sailing Toward a Beach Stop
Catamaran Sailing Trips, Sailing and Snorkeling Trips, Sailing Tours, St Maarten Sailing Tours, Tour Reviews

Tropical Catamaran Snorkeling, Sailing And Beach Experience

5.Tropical Catamaran Snorkeling, Sailing And Beach Experience

★★★★★★★★★★5.0 · 285 reviews · from $132

Spend about six hours aboard Eagle Tours’ catamaran from Bobby’s Marina, stopping at Little Bay and other beaches for snorkeling and swimming. The crew provides instruction, gear, a barbecue buffet, snacks, and an open bar. Captains and crew members such as Josh, James, Tamara, Fritz, and Tyrell are often praised for attentive service, though conditions and group size vary.

“It was amazing, the crew was friendly and entertaining. They engaged us all day. The food was also delicious!”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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