Recent Searches
Clear
Questions? (888) 651-9785(888) 651-9785

Top Philipsburg Cruises, Sailing & Water Tours

Category
Select Dates
Today
Tomorrow
Filter




Sort: Featured

22 Tours and Activities

Sort by:Featured

Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Day Trips

Ultimate Prickly Pear and Anguilla Experience

Sail by catamaran to Anguilla and Prickly Pear on this full-day adventure from St Maarten. Leaving from Simpson Bay, cruise over to the Prickly Pear Cays to snorkel among the tropical fish and abundant coral. Enjoy an open bar and snacks as you head for Anguilla to explore the undersea life there. Stop at a seaside restaurant for a traditional barbecue lunch, and toast the sunset with champagne on your way back to St Maarten's docks.
...  More
  • 8 hours
  • Free Cancellation
From  
US$129.00
From  
US$129.00
Learn More
  • 8 hours
  • Free Cancellation

Sailing Trips

Small-Group Day Sail in St Maarten

Cruise on the ultramarine waters off St Maarten during this 5-hour yacht excursion from Simpson Bay. Step aboard the family-friendly yacht, the 'Random Wind', to meet your friendly captain and crew as the boat departs the pier. Find a comfortable spot on one of the boat's cushioned seats in the shade or sun and get to know your small group of 32 people or less as you watch the coastline fade into the distance. Journey to both the French and Dutch sides of the island to visit several beaches and relax in the soft sand. Go snorkeling, stand up paddleboarding or try out the Tarzan swing. Eat a homemade lunch and sip drinks from the top shelf bar.
...  More
  • 5 hours
  • Free Cancellation
From  
US$118.99
From  
US$118.99
Learn More
  • 5 hours
  • Free Cancellation

Day Cruises

Anguilla Getaway Cruise

Explore the island of Anguilla on this 7-hour power boat excursion from Philipsburg. Snorkel, swim, and explore the island, then stop at a local restaurant for lunch. Open bar, use of snorkel equipment, and round-trip hotel transportation included.
...  More
  • 7 hours
  • Free Cancellation
From  
US$139.00
From  
US$139.00
Learn More
  • 7 hours
  • Free Cancellation

Sailing Trips

Anguilla Day Trip from St Maarten Including Lunch

Sail to Anguilla aboard a luxury catamaran on this full-day trip from St Maarten. Stop at Prickly Pear Cay to lounge in the shallows off the small island's the pristine beach or snorkel among the tropical fish that inhabit the colorful coral reef. Visit lively Road Bay Beach for a barbecue lunch at Roy's Bayside Grill, then hit up some of the beach bars before climbing back aboard the two-hulled sailboat for the trip back to your departure point. Round-trip transportation from select hotels on St Maarten is included, depending on day of tour.
...  More
  • 8 hours
  • Free Cancellation
From  
US$120.00
From  
US$120.00
Learn More
  • 8 hours
  • Free Cancellation

Catamaran Cruises

The Original Farewell Tour - sailing Around the Island - snorkel, beach...

Spend the day sailing St Maarten's waters on a catamaran, stopping at secluded islands and snorkeling in the calm Caribbean waters. During this full-day excursion, explore some of the islands unspoiled beaches and snorkel off the shore. Dig in to a 3-course gourmet lunch at one of Grand Case's famed restaurants accompanied by French wine. Climb back aboard the boat for a final ocean jaunt and a chance for one last dip in the ocean. Round-trip transportation from St Maarten hotels is included.
...  More
  • 8 hours
  • Free Cancellation
From  
US$129.00
From  
US$129.00
Learn More
  • 8 hours
  • Free Cancellation

Day Cruises

Private Speed Boat Charter to Anguilla

Venture out from St. Maarten to the island of Anguilla on your own private speedboat. Charter a boat for the day and customize your own itinerary with the captain based on your interests and the weather conditions. Snorkel in the vibrant coral reef systems to discover native marine species, swim in the pristine turquoise waters, and soak up the warm Caribbean sun with a drink on hand.
...  More
  • 1 day
  • Free Cancellation
From  
US$590.00
From  
US$590.00
Learn More
  • 1 day
  • Free Cancellation

Dinner Cruises

Tango Caribbean Dinner Cruise

Watch the sunset and dine on Creole fare aboard a catamaran during this 3-hour excursion from St Maarten. Sip drinks from the open bar and munch on complimentary appetizers while the sun sinks below the horizon. Once twilight falls, enjoy a buffet-style Creole dinner, followed by dessert and Caribbean rum. Hit the dance floor to island beats while the boat sails back to the marina.
...  More
  • 3 hours
  • Free Cancellation
From  
US$80.00
From  
US$80.00
Learn More
  • 3 hours
  • Free Cancellation

Night Cruises

St. Martin Sunset Sail

Sail along the coast of St. Martin during sunset on this 90-minute excursion. Enjoy snacks, drinks and entertainment as you take in the exquisite colors of a Caribbean sunset. Pick a spot on the spacious deck of the boat or up front in the nets stretching between the two hulls of the catamaran to relax, relish the ride and watch the sun sink below the horizon, ending another beautiful day in paradise.
...  More
  • 1 hour 30 minutes
  • Free Cancellation
From  
US$40.00
From  
US$40.00
Learn More
  • 1 hour 30 minutes
  • Free Cancellation

Sailing Trips

Champagne Sunset Cruise in St Maarten

Watch the sun set from the deck of a catamaran during this 2-hour champagne cruise from Philipsburg. Sip unlimited champagne and enjoy delectable appetizers while you sail down the coast of St Maarten towards Long Bay. Say goodbye to another day in paradise as the sun sinks below the horizon.  
...  More
  • 2 hours
  • Free Cancellation
From  
US$49.00
From  
US$49.00
Learn More
  • 2 hours
  • Free Cancellation

Full-day Tours

The Original Eco Tour - Full day around the Island of Sint Maarten / St Martin

Cruise around St Maarten with stops at Tintamarre, Creole Rock and Grand Case on this full-day sailing excursion. Explore the lovely natural beauty of Tintamarre, then head to Creole Rock for some of the island's best snorkeling. Go ashore in Grand Case, the St Maarten's culinary capital, for a gourmet lunch including wine. Cruise down the coast after lunch past Marigot Bay and Sunset Beach while enjoying an open bar. Round-trip transportation from St Maarten hotels is included.
...  More
  • 8 hours
  • Free Cancellation
From  
US$129.00
From  
US$129.00
Learn More
  • 8 hours
  • Free Cancellation

Cultural Tours

NEW TO VIATOR

Anguilla Day Trip to Shoal Bay with Lunch

Why spend a full day on a catamaran and endure the rocky waves to arrive to Anguilla just for lunch and not even enjoy their beautiful beaches? Come with us and arrive in Anguilla in 20 minutes via ferry boat and actually spend time on the beautiful beach, walk on the powdery sand and enjoy the sun and local food! You will travel via high-speed ferry boat to the shores of this laid-back tropical paradise, known for its white sand beaches and luxurious amenities. Upon arrival to Anguilla, our driver awaits you in a mini bus and will give you a mini tour of Anguilla showing you the cool spots before you get to one of the number one beaches in the world, Shoal Bay. Arriving on Shoal Bay, get ready for an afternoon of relaxing. Lunch is included on this tour & 1 free drink. Don't spend a full day on a boat as a day trip! Join us and zoom across the sea from Marigot to Anguilla in 20 minutes!
...  More
  • 7 hours
  • Free Cancellation
From  
US$162.00
From  
US$162.00
Learn More
  • 7 hours
  • Free Cancellation

Catamaran Cruises

SXM LUXURY CATAMARAN GROUP TOUR

Spend the day cruising along St. Maarten’s shores on a luxury catamaran. Booking this tour in advance means you’re guaranteed some time out on the water, taking in the coastal sights, swimming, and snorkeling at your leisure. You’ll post up off of Maho Beach to see the planes take off and land, go fishing or kayaking, and enjoy lunch on board midday.
...  More
  • 6 hours
  • Free Cancellation
From  
US$165.00
From  
US$165.00
Learn More
  • 6 hours
  • Free Cancellation

Day Cruises

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

Sail by catamaran to Anguilla, visiting Shoal Bay and Cove Bay, on this full-day adventure from St Maarten. Leaving from Simpson Bay, cruise over to the nearby island and transfer to an overland vehicle to reach Shoal Bay. Set up your provided umbrella and lounge chair on one of the world's ten best beaches to enjoy the island scenery. Sip tropical drinks and munch on snacks, then dig in to a barbecue lunch before returning by land and sea to St Maarten. 
...  More
  • 7 hours 30 minutes
  • Free Cancellation
From  
US$135.00
From  
US$135.00
Learn More
  • 7 hours 30 minutes
  • Free Cancellation

Ports of Call Tours

Around the island small group, snorkeling, day trip with multiple stops

Enjoy a fun and laidback day sailing around the Dutch and French sides of St. Maarten during this half-day excursion. Climb aboard your vessel and stop along the way to swim, snorkel, paddleboard, and soak up the warm Caribbean sun. Observe local wildlife, like sea turtles and iguanas, and enjoy lunch, snacks, and an open bar over the course of the day.
...  More
  • 5 hours 30 minutes
  • Free Cancellation
From  
US$130.00
From  
US$130.00
Learn More
  • 5 hours 30 minutes
  • Free Cancellation

Catamaran Cruises

Sailing with Skipper Andrea catamaran in the French Marine Park

Take an intimate sailing tour off the coast of St. Maarten with a group of just 12 people or fewer. You’ll sail through the French Marine Park and visit Tintamarre Island, where you’ll likely have the beach to yourself. Go swimming and snorkeling with provided equipment, keeping your eye out for rays and sea turtles. Enjoy a lunch and open bar before heading back, stopping at Rocher Creole, Happy Bay, and Friars Bay on the way.
...  More
  • 6 hours
  • Free Cancellation
From  
US$147.33
From  
US$147.33
Learn More
  • 6 hours
  • Free Cancellation

Catamaran Cruises

Small-Group Speed Boat Adventure

Explore St. Maarten with your own captain and crew on this 6-hour charter. Set your own schedule to visit the parts of the island that interest you the most. Drinks, food, and use of snorkel equipment provided.
...  More
  • 7 days
  • Free Cancellation
From  
US$1,126.00
From  
US$1,126.00
Learn More
  • 7 days
  • Free Cancellation

Private Sightseeing Tours

St Maarten Private Boat Charter

Choose your own adventure with this 7-hour private boat charter from St Maarten. With just your friends and family, board a private powerboat and jet anywhere you like in the surrounding turquoise Caribbean Sea. Consult your friendly captain for tips on the hidden gems in the area or head straight for the neighboring island of Anguilla. Go snorkeling amidst stands of vibrant coral, feed the multicolored reef fish or simply chill out on a pristine beach. Enjoy drinks from the open bar and the ability to customize your itinerary.
...  More
  • 7 hours
  • Free Cancellation
From  
US$1,200.00
From  
US$1,200.00
Learn More
  • 7 hours
  • Free Cancellation

Cultural Tours

NEW TO VIATOR

3 countries. 2 islands. 1 Day. (St Maarten,St Martin,Anguilla)

Get a taste of 3 countries on 2 islands all in 1 day! Get your first island tour on the Dutch side of Sint Maarten (Holland), then you will end up on the French side of St Martin (France) Visit the famous beach of Anguilla (UK) called Shoal Bay Beach! Here you will you witness the white powdery sand beach and crystal clear water while sipping on some rum punch.
...  More
  • 7 hours
  • Free Cancellation
From  
US$189.00
From  
US$189.00
Learn More
  • 7 hours
  • Free Cancellation

Catamaran Cruises

Sunday Jazz and Snorkeling in Anguilla

Cruise to Anguilla on a power catamaran on this 7-hour tour from St. Maarten. Snorkeling stops and lunch of traditional Caribbean fare, accompanied by live jazz, included.
...  More
  • 7 hours
  • Free Cancellation
From  
US$119.00
From  
US$119.00
Learn More
  • 7 hours
  • Free Cancellation

Private Sightseeing Tours

Private Snorkeling Charter to Creole Rock 3 hours

Explore St Maarten  Shore and part of nature reserve of St Martin on a 3.5 - hour speedboat and snorkeling trip. With your expert captain and your private boat , jet out from Philipsburg to several nearby locations like the uninhabited Creole rock . Jump into the water and snorkel at the biodiversity hotspot Creole Rock, then enjoy the ride and great boat experience . Sip beers and soda from the onboard bar as your captain shares his knowledge of St Maarten and the surrounding waters with you.Option load your boat with SeaBobs - the greatest underwater machines on the market 
...  More
  • 3 hours 30 minutes
  • Free Cancellation
From  
US$880.00
From  
US$880.00
Learn More
  • 3 hours 30 minutes
  • Free Cancellation

Jet Boats & Speed Boats

NEW TO VIATOR

Power Boat To St Barths

Enjoy a hi speed 35min to St Barths aboard our well appointed power boats. Meet & Pickup directly at cruise pier for your convinience. Enjoy shopping time in Gustavia or head to one of their famous beaches or do both... Keep your eyes open as you never know who you will see walking next to you while strolling in town or who is swimming next to you at the beach. Celebrities frequent this island year round. Come enjoy the lifestyles of the rich and famous! See you soon
...  More
  • 2 to 8 hours
  • Free Cancellation
From  
US$1,650.00
From  
US$1,650.00
Learn More
  • 2 to 8 hours
  • Free Cancellation

Private Sightseeing Tours

Private Charter to Anguilla from St Maarten

With your private party, step aboard the 50-foot (15.2-meter) speedboat and embark on a day tour to Anguilla. Make use of the sound system, comfortable lounge area, open bar, and fuel up with a gourmet lunch on the trip. Once in Anguilla, use your time however you like. The dedicated captain and staff ensure your group has personalized attention and a flexible itinerary.
...  More
  • 5 to 7 hours
  • Free Cancellation
From  
US$1,350.00
From  
US$1,350.00
Learn More
  • 5 to 7 hours
  • Free Cancellation


Book online or call
(888) 651-9785
(888) 651-9785