Top St Maarten Cruises & Sailing

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.

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.

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.

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.

Tintamarre 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 Tintamarre, St. Maarten, and Pinel islands that lets you get close to local wildlife on 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.

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.

Watch the sunset and dine on Creole fare aboard a catamaran during this 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.

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.

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!

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!

Explore the waters around St. Maarten on a 6-hour speedboat tour. Avoid the cruise ship crowds and visit both the Dutch and French sides of the island in a family friendly, small group setting, which includes five stops to see different aspects of the marine environment. You’ll swim and snorkel in a sea turtle habitat, sting rays and tropical fish on uninhabited islands. Sunbathing on some of the finest white sand beaches the Caribbean has to offer while feeling the rush of commercial jets landing directly over your head at the famous airport. Along the way, your captain will share entertaining and engaging commentary and you’ll sip drinks and indulge in unlimited snacks, all included in the price.

Explore the Islands Your Way – À la Carte Style Set out on a private boat charter for a half-day or full-day adventure. You choose the destinations and activities we’ll handle the rest. Whether it’s snorkeling, swimming, sunbathing, or just cruising around, we’ll help plan the perfect day with great recommendations and hidden gems. Kick back with complimentary drinks and snacks, enjoy the clear blue water with your crew. It’s your boat, your adventure, let the good times roll! Please note: If you are coming from the Cruise Ship please select your trip with the option: CRUISE SHIP/CRUISE PORT for a convenient Pick Up at the Dock Maarten Marina located at a walking distance form the cruise Ship terminal. See below itinerary: https://maps.app.goo.gl/T1gTeLggjegWVYfN8

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.

Buzz around St. Maarten in your own private custom jeep, and have the freedom to go at your own pace. You don’t need to stick to a fixed itinerary while you explore, or share this experience with others outside your group. Just choose the color and make of the jeep you’re looking for, and the rental period, then hit the streets, with your included island map.

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.

Get a taste of local culture and history with this highlights tour of St. Maarten. Ideal for first-timers to the island, enjoy an itinerary that includes monuments, museums, and beaches, as well as opportunities to shop. Learn about St. Maarten directly from your guide as you visit Cole Bay, Topper's Rhum Distillery, and Maho Beach. And don’t worry about getting sore feet when going to each destination, with transportation provided between attractions.

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.

Cruise around St. Maarten in style and watch the sunset from the water with this sunset bubbly cruise from Simpson Bay on a 65-foot (20-meter) catamaran. Admire the views as you cruise along the Golden Coast, past Maho Beach and Mullet Bay, while savoring snacks and drinks, including free flowing prosecco, from an open bar onboard.

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!