Top St Maarten Sailing Trips

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Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 21 Reviews

Sail in the Caribbean paradise of St Maarten on a casual yet upscale cruise within walking distance from the cruise ships! Your day includes real sailing, ... 

Location: Philipsburg, St Maarten
Duration: 5 hours

From USD $118.99

Anguilla Day Trip from St Maarten Including Lunch

5 star rating: Highly Recommended 73 Reviews

Discover the paradise beaches of Anguilla on this full-day trip from St Maarten. Sail aboard a catamaran and stop at Prickly Pear Island, one of Anguilla’s ... 

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

Champagne Sunset Cruise in St Maarten

4.5 star rating: Recommended 5 Reviews

Experience the romance of a Caribbean sunset on a Champagne cruise in St Maarten. While you sail along the coast on a luxury catamaran, enjoy Champagne and ... 

Location: Philipsburg, St Maarten
Duration: 2 hours

From USD $49.00

St Maarten Sailing and Snorkeling to St Barts

4.5 star rating: Recommended 8 Reviews

Cruise to St. Barts on a sailing, snorkeling, and sightseeing tour that departs from Dock Maarten. Stops include Île Fourchue, Gustavia, and Colombier on ... 

Location: Sint Maarten, Netherlands
Duration: 9 hours

From USD $139.00

Full Day Sail to Tintimarre Island

5 star rating: Highly Recommended 4 Reviews

Sailing is a relaxing experience while on a big and comfortable catamaran. The professional crew will entertain and take good care of you. This experience ... 

Location: Simpson Bay, Sint Maarten
Duration: 10 hours

From USD $150.00
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