Top St Maarten Cruises & Sailing

Spend a full day exploring St. Maarten’s breathtaking coastline aboard a luxury catamaran, complete with activities and relaxation. From spotting planes at iconic Maho Beach to snorkeling in crystal-clear waters, fishing, or kayaking, the experience is yours to tailor. Drop by Long Bay, Happy Bay, and other beautiful spots. Enjoy all of this at a leisurely pace, with a freshly prepared lunch served onboard to complete the perfect day.

Getting out on the water is one of the best ways to experience St. Maarten, but arranging a boat day on your own can be complicated and expensive. This fun catamaran cruise from Simpson Bay makes it simple, with a comfortable vessel and planned stops built into the day. Relax on cushioned seating as you journey along the water, then dive in when the catamaran anchors to enjoy snorkeling or stand-up paddleboarding.

Reaching Anguilla’s most beautiful bays and beaches isn’t easy without a boat. This full-day powerboat excursion from Simpson Bay in St. Maarten gives you direct access to remote stretches of coastline, with multiple stops for swimming, snorkeling, and relaxing around the island. Enjoy lunch served onboard and sip from drinks served at the open bar throughout the day—while the crew handles all the navigation and logistics.

Experience the best of St. Martin and St. Maarten in a short amount of time on this tour that explores both sides of the island. Start on the French side, Saint-Martin, for a visit to Oyster Pond, and a drive through the fishing village of Grand Case. Then head to Sint Maarten on the Dutch side to visit the world-famous Maho Beach and Bell's Lookout Point.

Sail to Anguilla aboard a catamaran on this full-day cruise from St. Maarten. Stop at Prickly Pear Cay to lounge in the shallows of the small island's pristine beach or snorkel among the tropical fish that inhabit the colorful coral reef. Enjoy a buffet lunch right onboard and an open bar.

Escape the crowds and discover the delights of St. Martin island in style on a private, custom catamaran cruise that takes you th pristine beaches and nature-rich snorkel spots. Enjoy the catamaran all to yourself, and choose between two different durations and itineraries—both include a gourmet lunch, plus time to snorkel, swim, and paddleboard.

End another day in tropical paradise in perfection on this sunset cruise. Hop on board your trimaran vessel late in the afternoon, just in time to set sail as the sun sinks beneath the horizon. You’ll be served snacks and drinks to enjoy as you admire the views. This is a chilled out small-group activity that’s ideal for couples.

Snorkel at some of St. Maarten's most spectacular sites, such as Pinel Island, Creole Rock, and Tintamarre Island on this full-day eco-adventure onboard a sleek powerboat. Stop for a gourmet lunch in Grand Case, then head to Mullet Bay for some time on the beach. Drink up from the open bar. On the return trip, stop at Maho Beach to watch the airplanes landing at the nearby airport.

Explore St. Maarten with your own captain and crew on this 3-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.

Tintammare and Pinel islands are known for beauty and excellent snorkeling, but getting there from St. Maarten can be difficult. Simplify things with this small-group half-day snorkeling and beach tour to Tintammare, St. Maarten, and Pinel islands that lets you get close to local wildlife land and in the sea. Relax on the beach, go snorkeling, or do a bit of both. If you’re lucky, you might see some sea turtles.

Step aboard our spacious catamaran, and begin your 3-hour sightseeing and snorkel cruise! Relax as we cruise along the coast with party music playing, and let the captain point out landmarks, mega yachts, and landing aircraft near our famous airport. For those looking for adventure, snorkel among vibrant marine life and colorful coral reefs. Our crew will serve you from our floating bar, making it easy to stay refreshed while you float, snorkel, or relax on the golden sands. Prefer to stay on the boat? Dance, sunbathe, or unwind in the shaded cockpit while enjoying the lively atmosphere. Our open bar offers unlimited beer, iced Rum Punch, sodas, and juices, paired with freshly made French baguette sandwiches. After your beach break and snorkeling adventure, we’ll cruise back to Philipsburg, where you’ll have time to explore the town or return to your cruise ship. The perfect outing of fun and relaxation awaits! We fill up fast as we welcome all island and cruise ship visitors!

Board sail cat Mambo at Simpson Bay Resort Marina for a leisurely sail across the channel to Cove Bay, Anguilla and then onto Rendezvous Bay. Rendezvous Bay welcomes you with a pristine, white, sandy beach. Enjoy crystal-clear waters for swimming, cooling off, or lounging in the water with a noodle! Relax, you are here to spend the day with great views of St. Maarten across the ocean. At noon, a delicious lunch is served right on board the sailing catamaran. When your food has settled, opt to walk Rendezvous Bay...2 miles of powdery sand to stretch your legs. The call to leave comes all too soon. Board Mambo again and sail home to relaxing rhythms and the sound of the waves hugging the hulls. Your tropical experience is complete. “Tranquility wrapped in blue” is how we like to describe Anguilla!

Explore St. Maarten’s natural landscape away from the crowded beaches on a boat cruise that departs from Bobby’s Marina. To ensure your comfort and a personal experience, the boat crew provide a buffet lunch, open bar, and snorkeling gear. Stops on the itinerary range from top landmarks to secluded snorkeling locations often missed by visitors.

This ONE WAY transfer is an excellent choice for any luxury transportation need. Whether it’s a Business trip or a Birthday trip we have you covered. We also provide more economical transfer options. Same great service. Our Chauffeur will be waiting for you at arrival and is easily identifiable. Simply look for a hand held sign with the lead travelers name on it. All incoming flights are monitored in case of delays. After being greeted, we then escort you to your vehicle and onto your chosen destination.

Breathe naturally and take in the beauty of the surrounding scenery! You will be able to walk and breathe on the bottom of the Caribbean sea, just like on the surface. You’ll transported by boat to our platform in the middle of water where you will be welcome by our enthusiastic team, our guided will explain the the tour and divide the group in two, while some of you will enjoy snorkeling for 30 minutes and the other group will enjoy the Sea Trek for 30 minutes. At the end of the snorkeling session, we will return our gear and get ready to enjoy the Sea Trek, while the other group does the opposite. Once you are ready to do the Sea Trek, you will descend 2 to the seabed. This descent is little by little by a ladder with 20 steps (20 ft), so you become familiarized with the water environment and the use of the Sea Trek helmet. Once you reach the bottom, you will be guided by a path marked by railings, for a more comfortable underwater walk.

Experience the best of Saint Maarten with this one-of-a-kind ATV and Jet Ski combo adventure. Cruise through both the French and Dutch sides, stopping at scenic lookouts, iconic landmarks, and Coralita Beach to spot wild iguanas. Wrap up your adventure in Philipsburg with a high-energy Jet Ski ride, all led by a local guide who showcases the island’s hidden gems.

Charter your own private speedboat for a half or full day and explore St. Maarten at your own pace. Choose the destinations you would like to visit with your captain based on your needs and the weather conditions. Spend the day swimming and snorkeling in pristine waters and soaking up the sun onboard or on secluded beaches. Enjoy complimentary drinks on board during this private tour.

Combine rides on the Flying Dutchman, the Schooner Ride and the Sentry Hill Zipline on this thrilling combination tour. First, ascend to St. Maarten's highest point on the Sky Explorer for excellent views, then zoom down the mountain on the Flying Dutchmen. Head back up the mountain and clip on to the Sentry Hill Zipline to get views over the island. Finish up with an inner tube ride down the mountain on the Schooner Ride.

Sail by catamaran to Anguilla and Prickly Pear on this full-day adventure from St. Maarten. 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. We will also enjoy a buffet-style lunch onboard, and toast the sunset with Champagne on the way back to St. Maarten's docks.

Sail along the coast of St. Martin during sunset on this 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 upfront 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.

Join us for a 6 Hours sightseeing, sailing, and snorkeling experience. Your comfort and safety are our main concern. We will do an easy South side Coastal sailing Dutch Side with 2 or more stops for snorkeling, beach time and even spotting the planes as they land on our famous Maho Beach. Caribbean Style buffet lunch, Open bar all day, Snorkeling instruction and equipment, Attentive friendly and professional crew are all the ingredients for a successful day in Sint Maarten! *** NOTE: Alternate stops may be chosen according to weather conditions.

Just north of St. Maarten, the stunning island of Anguilla awaits—known for its powdery white-sand beaches, turquoise waters, and relaxed Caribbean charm. Embark on an unforgettable journey aboard our spacious and powerful catamaran, where you’ll experience the very best of Anguilla in comfort and style. With indoors and outdoor seating our catamaran’s stable design and smooth cruising speed of 15-20 knots promise a comfortable ride over gentle Caribbean waves. Highlights include: • World-Famous Beaches – Sink your toes into the soft sands of the many beautiful beach. • Snorkeling and Swimming – Explore Anguilla’s vibrant underwater life with snorkeling gear included. • Full Bar & BBQ Lunch – Enjoy our signature cocktails and a delicious BBQ lunch onboard. Whether you’re seeking relaxation or adventure, our Anguilla Day Charter is your ticket to paradise. Limited spots fill quickly, so book now!

This is the perfect balance of adventure, nature, and culture a curated island hopping experience that shows you the best of both land and sea in one unforgettable day. Whether you’re traveling as a couple, a family, or with friends, this boat charter delivers memories that last long after the sun sets. Highlights: • Snorkel the vibrant reefs at Creole Rock • Swim with sea turtles at wild Tintamarre Island • Unwind on the soft sands of Pinel Island • Enjoy French Gourment Sandwiches • Watch planes land overhead at the iconic Maho Beach A local guide will provide live commentary on board Guaranteed on-time transfers from your cruise ship and back Use of snorkelling equipment and flotation noodles is included Don't miss your opportunity to book your unforgettable trip with All About Boat Charters.