Philipsburg Sailing Trips

Philipsburg Sailing Trips

Cruises, Sailing & Water Tours See all

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Anguilla Day Trip from St Maarten Including Lunch

5 star rating: Highly Recommended 60 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 ...  Read more

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 21 Reviews

Ever dreamed of sailing a real racing yacht? Well don't miss out on this fantastic opportunity to race in the warm blue waters and brisk trade winds of the ...  Read more

Location: Philipsburg, St Maarten
Duration: 2.5 - 3 hours

From USD $95.00

Day Trip to the Island of Prickly Pear from St Maarten

5 star rating: Highly Recommended 66 Reviews

Any trip to St Maarten would not be complete without a day trip to the gorgeous and unspoiled island of sun and sand - 'Prickly Pear Cay', and a swim ...  Read more

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 13 Reviews

Sail in the Caribbean paradise of St Maarten on a 5-hour cruise including homemade lunch and unlimited drinks from a top shelf open bar. Relax on a ...  Read more

Location: Simpson Bay, St Maarten
Duration: 5 hours

From USD $108.99

St Maarten Catamaran Snorkel Sail

5 star rating: Highly Recommended 14 Reviews

Set sail for a full day at sea in St Maarten You'll spend a leisurely day in true Caribbean style, relaxing on a deserted island, going for a snorkel and ...  Read more

Location: Philipsburg or Simpson Bay, St Maarten
Duration: 8 hours

From USD $118.99

St Maarten Sunset Schooner Cruise

4.5 star rating: Recommended 3 Reviews

Enjoy a Caribbean sunset from the water on this St Maarten cruise by historical schooner. On board a sailboat that’s more than 100 years old, ...  Read more

Location: Simpson Bay, St Maarten
Duration: 2 hours

From USD $38.99

Champagne Sunset Cruise in St Maarten

4 star rating: Recommended 3 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 ...  Read more

Location: Philipsburg, St Maarten
Duration: 2 hours

From USD $44.99
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Only Show: Day Cruises | Dinner Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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