Top Philipsburg Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

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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 $118.99

Self-Drive Boat Tour and Snorkel from Simpson Bay

5 star rating: Highly Recommended 17 Reviews

Explore the western coast of St Martin island — from Simpson Bay in Dutch St Maarten to Creole Rock on the French side, St-Martin — on this self-drive boat ... 

Location: Simpson Bay, St Maarten
Duration: 2 hours 30 minutes

From USD $69.99

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

Prickly Pear Day Sail and Snorkel from St Maarten

5 star rating: Highly Recommended 9 Reviews

Enjoy a sailing, snorkeling and sightseeing adventure to the Caribbean islands of Prickly Pear and Anguilla on this 8-hour tour from St Maarten. Starting at ... 

Location: Philipsburg, St Maarten
Duration: 8 hours

From USD $119.00

Tango Caribbean Dinner Cruise

5 star rating: Highly Recommended 45 Reviews

Experience the true Caribbean way on this evening dinner cruise! Guests are treated to an open bar and snacks as the catamaran sails along the coast of St. ... 

Location: Simpson Bay, St Maarten
Duration: 3 hours

From USD $80.00

Anguilla Getaway Cruise

5 star rating: Highly Recommended 2 Reviews

Come experience a great atmosphere with a personal touch on this full day excursion to explore to beautiful island of Anguilla. Snorkel with tropical fish and ... 

Location: Philipsburg, St Maarten
Duration: 7 hours

From USD $139.00

Private Speed Boat Charter in St Maarten

Board on a premium style speed boat for a private day charter around St Martin/St Maarten! You can fully personalize your day and do exactly what you want. ... 

Location: Philipsburg, Sint Maarten
Duration: 1 day

From USD $590.00

Anguilla Day Trip from St Maarten: Catamaran Sail with Snorkeling at Shoal Bay

4.5 star rating: Recommended 14 Reviews

Enjoy a full day of sand and sea in Anguilla, sailing aboard a spacious catamaran from St Maarten. You’ll cruise with a fun and friendly crew to Cove Bay and ... 

Location: Simpson Bay, St Maarten
Duration: 7 hours 30 minutes

From USD $135.00

St. Martin Sunset Sail

4.5 star rating: Recommended 14 Reviews

Nothing compares to the exquisite colors of a Caribbean sunset. Enjoy the romantic mood that is automatically set as the sun disappears into the waters off ... 

Location: Simpson Bay, St Maarten
Duration: 90 minutes

From USD $40.00

Half Day Snorkeling and Beach Tour

5 star rating: Highly Recommended 2 Reviews

This is a perfect 3.5 hours getaway from the crowd. Available with  9:00 am morning or 12:45 pm afternoon departure. Includes sightseeing in the  Simpson bay ... 

Location: Philipsburg, St Maarten
Duration: 3 hours 30 minutes

From USD $75.00

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

Prickly Pear Anguilla By Boat & Snorkeling

Our Prickly Pear stop includes snorkeling and swimming, then head to a beach on Anguilla for lunch at Prickly Pear and a beach for the afternoon in Anguilla. ... 

Location: Philipsburg, Sint Maarten
Duration: 8 hours

From USD $285.00

Sunseeker 52 & Seabobs Private Charter

Private charter on Luxury Sunseeker 52  Visit all the best places around Sint Maarten , Tintamarre island, Creole rock, Pinel island and much ... 

Location: Philipsburg, Sint Maarten
Duration: 6 hours

From USD $2,560.00

Sunday Jazz and Snorkeling in Anguilla

Enjoy a 7-hour Sunday cruise by power catamaran to the beach island of Anguilla, with an experienced captain and mate. Cruise around the lagoon and see as the ... 

Location: Philipsburg, Sint Maarten
Duration: 7 hours

From USD $119.00

3 Beaches by Boat

Explore both Dutch St. Maarten by waters and sail for a memorable experience aboard a motorized catamaran accommodating both open air sunshine, and shaded ... 

Location: Philipsburg, Sint Maarten
Duration: 4 hours

From USD $187.20

Full-Day St Maarten Catamaran Charter

Join Magic time our comfortable, fast Power Catamaran, we can take a MAX of 26 Guests with all the comfort and space. We have 80% shade on board. Swimming ... 

Location: Philipsburg, Sint Maarten
Duration: 7 days

From USD $1,126.00

Private Sailboat Charter in St Maarten

Spend the day out on the beautiful Caribbean Sea on this private sailing charter in St Maarten! Whether your group is two or 37 - you will be comfortable and ... 

Location: Simpson Bay, St Maarten
Duration: 5 hours

From USD $1,800.00

St Maarten Sea Adventure with Snorkeling at Creole Rock

Visit some of St Maarten/St Martin's most famous attractions on this 6-hour tour! See the sights by water including Maho Beach, snorkeling at Creole Rock plus ... 

Location: Simpson Bay, St Maarten
Duration: 6 hours

From USD $950.00

St Maarten Private Boat Charter

Relax on a private boat just for you and your family or friends. Enjoy a day on a fast powerboat for a day trip Around St Martin/Maarten. Plan your day ... 

Location: Philipsburg, St Maarten
Duration: 7 hours

From USD $1,200.00

Sightseeing Cruise to Anguilla from St Maarten

Visit the pristine island of Anguilla, where famous celebrities vacation, on this sightseeing cruise from St. Marteen. With an exclusive group and tour guide ... 

Location: Philipsburg, St Maarten
Duration: Flexible

From USD $200.00

Private Speed Boat Charter to Anguilla

5 star rating: Highly Recommended 1 Review

Board a premium-style speed boat for a private day charter around Anguilla! You can fully personalize your day and do exactly what you want. Enjoy the ... 

Location: Philipsburg, Sint Maarten
Duration: 1 day

From USD $940.00

Private Sunset Cruise in St Maarten

This amazing sunset trip on a private boat can accommodate up to 10 passengers. Make great memories while in St Maarten. Perfect for couple or small groups!

Location: Philipsburg, Sint Maarten
Duration: 2 hours

From USD $580.00

St Barth Private Speed Boat Charter from Philipsburg

Discover St Barthelemy on a private speedboat charter. Visit the best snorkeling sites, stop at some of the most pristine beaches like St Jean or Colombier ... 

Location: Philipsburg, Sint Maarten
Duration: 6 hours

From USD $1,450.00

St Maarten Catamaran Snorkel Sail

5 star rating: Highly Recommended 19 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 ... 

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

From USD $129.00
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