5 Sailing Trips in St Maarten to Build a Day Around

1.The Best Catamaran Day Sail in St Maarten

★★★★★★★★★★5.0 · 1,552 reviews · from $139Our pick

Join Captain Scott, Anna, Jackie, and canine first mate Queenie aboard Random Wind for a relaxed five-hour sail from Simpson Bay. You’ll visit Mullet Bay and Little Bay, snorkel, paddleboard, swim, swing into the sea, and enjoy grilled chicken, Caribbean rice, salad, baguette, snacks, and an open bar.

“Best Experience on the Island. Great Staff. Very Professional. Very clean and well kept vessel. Random Wind is a beautiful ship. Waters were beautiful. The food was great. The drinks were great. The Tarzan swing was amazing. Wasn't crowded like so many other boats offering the same. Saw a plane landing while we were sailing past Maho, amazing experience. Snorkeling at Little Bay was a blast. Tarzan Swing at Simpson Bay was incredible. Would recommend as a must for all visitors. Laid Back and Fun. S2S Reviews”

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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. Snorkel with supplied gear, use paddleboards and a floating mat, enjoy cooked lunch and unlimited drinks, then watch aircraft pass over Maho Beach.

“The best experience we had during our stay in St. Maarten, our Captain and Crew were the best, they took amazing care of us! Drinks and Lunch were the perfect treat, wish it was longer we loved it!!”

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

★★★★★★★★★★5.0 · 402 reviews

Spend about seven hours aboard a private catamaran with Captain Mike and Elmira. Cruise St. Maarten’s coast, snorkel at Long Bay and Little Bay, visit Tintamarre when weather allows, and enjoy paddleboarding, a charcoal barbecue lunch, snacks, and an open bar. Your group of up to eight has the boat to itself.

“Captain Mike’s “tour guide” experience was wonderful! The wind didn’t lend to pinel and tintamarre so we stayed along the Dutch coast primarily. The food was incredible and the drinks plenty. Thank you again!”

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4.Tropical Catamaran Snorkeling & Sailing

★★★★★★★★★★5.0 · 353 reviews · from $132Best value

Spend about six hours aboard a catamaran from Bobby’s Marina with snorkeling at Little Bay, beach swimming, Maho Beach plane spotting, a Caribbean barbecue, and an open bar. Crews including Captain Josh, Charlie, Fritz, and JP have been praised for friendly service, though stops depend on weather and the boat may carry up to 50 people.

“It was wonderful and the staff were awesome. Good rum punches. The water was incredible we fed the fish”

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5.Private Full-Day Catamaran Sailing Charter in St Maarten

★★★★★★★★★★5.0 · 97 reviews

Spend about eight hours on a private catamaran from Simpson Bay, sailing around St Maarten and St Martin. Stop at La Samanna, Creole Rock, and Tintamarre Island for snorkeling, turtle swimming, a Caribbean BBQ, paddle boarding, and beach time. Louise and Tonya are names to ask about when booking, and the crew can adjust the day to suit your group.

“The captain and mate were amazing. We had the best day with them. We would do this with them everytime we come back”

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