The 4 Best St Maarten Sailing Trips

1.The Best Catamaran Day Sail in St Maarten

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

Spend about five hours aboard Random Wind with Anna, Jackie, and Captain Scott, sailing from Simpson Bay along both Dutch and French St. Maarten. Swim, snorkel, paddleboard, enjoy grilled lunch and an open bar, then swing into the sea from the boat’s Tarzan swing.

“Had a great cruise. Staff was excellent. Lovely day on the water with a little sailing. Great food and drinks. Enjoyed the snorkeling and jumping off the boat. Will definitely do this tour again next time we are in town.”

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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, sailing from Bobby’s Marina with Captain Benji and crew. Snorkel at Little Bay, watch planes near Maho Beach, swim at Mullet Bay, and enjoy lunch, fruit, cocktails, beer, soft drinks, paddleboards, and an 18-foot floating mat.

“We had the best time, the captain and crew were amazing , along with the food and beverage. Very comfortable and accommodating, music was a vibe. I would definitely recommend.”

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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 Elmira, stopping at Long Bay, Little Bay, and possibly Tintamarre. Snorkel, paddleboard, swim, or relax while the crew serves coffee, a BBQ lunch, snacks, and an open bar. Routes change with weather.

“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

Sail from Bobby’s Marina along St Maarten’s calmer leeward coast with Captain Josh, Charlie, Fritz, or another experienced crew. You’ll snorkel at Little Bay, swim at nearby beaches, enjoy a barbecue buffet and open bar, and may spot planes over Maho Beach.

“JP, Vince and Fritz were an amazing crew on the Too Rhum Punch! We had a wonderful time, lunch was fantastic (chicken, ribs, rice, salad and potato salad), drinks were flowing and vibes were awesome! There were about 25 ppl on thRead more”

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