St Maarten (St Martin) Sailing Trips

St Maarten (St Martin) Sailing Trips

Cruises, Sailing & Water Tours See all

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Day Trip to the Island of Prickly Pear from St Maarten

5 star rating: Highly Recommended 57 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 $109.99

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 15 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 ...  Read more

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

From USD $104.99

Anguilla Day Trip from St Maarten

5 star rating: Highly Recommended 53 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 $113.99

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 10 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 star rating: Recommended 2 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

3 star rating: Worth doing 1 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

St. Martin Pirates Day Cruise

4.5 star rating: Recommended 13 Reviews

Sail a tall ship on crystal clear Caribbean waters, hear exciting tales from the high seas and feel like a real pirate for a day! Spend an exciting and crazy ...  Read more

Location: Philipsburg, St Maarten
Duration: 3 hours

From USD $78.99

Tall Ship Sunset Cruise

4.5 star rating: Recommended 24 Reviews

See the sun set over the magical waters of the Caribbean! Sip on a glass of champagne while the sun sets a romantic back drop taking you into an evening of ...  Read more

Location: Philipsburg, St Maarten
Duration: 2 hours 30 minutes

From USD $62.99

Sailing and Shopping in St Maarten

Give back while you Sail and Shop in St. Maarten. This tour is within walking distance of the cruise terminal in Philipsburg. Enjoy this short, calm sail while ...  Read more

Location: Philipsburg, Sint Maarten
Duration: 60 minutes

From USD $35.00

Let's Go Sailing to St Barts

Tiime to sail to St Barts! Join us for an exclusive sail, snorkel and sightseeing tour leaving from Dock Maarten. Stops will include Ilet Fourchue, ...  Read more

Location: Sint Maarten, Netherlands
Duration: 9 hours

From USD $139.00
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Only Show: Brunch Cruises | Day Cruises | Dinner Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Sunset Cruises

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