Top Philipsburg Sailing Trips

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Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 20 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 $108.99

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
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