The 7 St Maarten Sailing Tours We Would Step Aboard

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, cruising from Simpson Bay to Mullet Bay and Little Bay. Swim, snorkel, paddleboard, kayak, swing into the Caribbean, and enjoy grilled chicken, salad, rice, bread, snacks, and an open bar. The group is limited to 30 people.

“Scotty and Anna are fantastic hosts and provided a great experience. We will sail with them again when we return to the island! Easy walk from the cruise port.”

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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 fresh snacks and a cooked lunch, and keep drinks coming from the open bar. The boat holds up to 36 people and returns to Philipsburg.

“Captain benji and his team were amazing sailing the Phoenix! The directions from the port to the meetup location were super easy to find. From the time we boarded the catamaran to the time we left we had smiles on our faces! Chef Camilla cooked us a delicious lunch! We got to see so much of the island it was such a joy. Thanks for a truly great day!”

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

★★★★★★★★★★5.0 · 402 reviews · from $1,700 whole boat, up to 8

Captain Mike and Elmira host a private seven-hour catamaran charter for up to eight people from AzianaBobby’s Marina. Expect snorkeling, swimming, paddleboarding, beach time, a charcoal BBQ lunch, snacks, and an open bar. Stops can change with weather, so bring a towel and non-spray sunscreen.

“Captain Mike and Elmira were nothing short of AMAZING! My eight year old son has not stopped talking about getting to drive/steer the boat with Captain Mike!! My 5 year old daughter has not stopped talking about how wonderful, “My Love,Read more”

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4.Tropical Catamaran Snorkeling & Sailing

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

Spend six hours aboard a spacious catamaran from Bobby’s Marina, sailing St Maarten’s calmer leeward coast. You’ll snorkel at spots such as Little Bay, swim from quiet beaches, watch planes near Maho Beach, and enjoy barbecue lunch, snacks, and an open bar. Crews may include Captain Josh, Charlie, Fritz, or other Eagle Tours staff.

“We had a fantastic experience with JP, Jasper and Jeb! They were a great crew and our family enjoyed the snorkeling, lunch and drinks. Had us back to make our cruise ship departure in plenty of time.”

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5.Tropical Catamaran Snorkeling, Sailing And Beach Experience

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

Sail St Maarten’s leeward coast aboard the Too Rhum Punch from Bobby’s Marina. You’ll snorkel at Little Bay, swim from quiet beaches, enjoy a barbecue buffet and open bar, and ride with a crew that may include Captain Josh, James, Tamara, or JP. Stops change with weather.

“It was amazing. I would highly recommend this tour. The crew were also so professional and fun. 5 Stars!”

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6.No1Sxm Sunset Sail Experience in St Maarten

★★★★★★★★★★5.0 · 240 reviews · from $65

Sail St Maarten’s coast aboard No1SXM, a small trimaran hosted by Pieter and Miriam. The 2-hour outing includes about 90 minutes of sailing, drinks, snacks, and sunset views past Maho Beach and Mullet Bay. Expect a quiet, nature-focused trip for up to 16 people, with dinghy transfers between the dock and boat.

“The owners are wonderful people. You will truly enjoy the experience. The owners are beautiful people. You will enjoy!!”

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7.St. Martin Sunset Sail

★★★★★★★★★★4.5 · 174 reviews · from $45Best value

Board the Lambada at Aqua Mania Adventures in Simpson Bay for a 90-minute sunset sail toward Long Bay. Captain Preston and the crew serve rum punch, beer, wine, soda, and light snacks while music sets a relaxed Caribbean party mood. Choose a deck seat or the catamaran’s forward nets, then return to the same marina.

“Boat was clean and in great working order. The staff was really friendly. Of course, snacks and drinks were delicious. The sunset view spectacular!”

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