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.

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.

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you to explore around our stunning islands waters at your own pace. Indulge in a selection of homemade meals, including fresh sandwiches, grilled dishes, and locally foraged ingredients, all crafted with care by our crew. With over 20+ years of experience sailing, Captain Robert will lead you on an unforgettable adventure, sharing tales of the islands, the sea, and his global voyages—each one more fascinating than the last. Choose how you spend your day: relax with a drink on deck, snorkel in crystal-clear waters, hike to hidden beaches. Should the weather not cooperate, we’ll happily reschedule your trip for another day. For any special requests or questions, feel free to contact us directly. Set sail with us for a day of Caribbean relaxation and adventure—tailored just for you!

Escape the crowds and discover the delights of St. Martin island in style on a private, custom catamaran cruise that takes you to pristine beaches and nature-rich snorkel spots. Enjoy the catamaran all to yourself, and choose between two different durations and itineraries—both include a 3-course gourmet lunch, plus time to snorkel, swim, and paddleboard.

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.

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.

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!

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.

Renting a boat in the Caribbean can be pricey and you’d have to worry about who would drive and navigate. This Tintemarre Island Catamaran Sailing Experience takes the stress out of planning by taking care of all the main details like your route and lunch. Stop at Long Bay, Creole Rock, Grand Case, and Tintemarre, and along the way, enjoy an open-bar, an attentive crew, and comfortable seating. Please note this tour operates only until August.

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 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’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.

Be as active or as relaxed as you like on this full-day cruise around St. Maarten aboard the “Hakuna Matata” catamaran. Families, couples, friends, and solo travelers are all welcome aboard. Stop at many beaches along the way—including places you wouldn’t reach any other way—and enjoy swimming, snorkeling, or just relaxing on the beach. Food and drinks are provided on board so you don’t need to bring your own.

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.

Sample some of St. Martin’s best rum and get a better understanding of how the amber nectar is made on a tour of Topper’s Rhum Distillery. Go behind the scenes to learn how the rum is fermented, distilled, and filtered, accompanied by over 20 samples at the tasting bar. Choose from 124 flavored rums, rum cake, rum-infused Italian gelato, as well as how to prepare food with rum.

Let us take you on a memorable tour of St Maarten. A must-do for any trip to the Caribbean, you can avoid the crowds by booking with us and exploring the wonders of the town at your own pace. As this is a private tour, we can cater to your needs. Swim in Mullet Bay, enjoy some duty-free shopping, feast on the local cuisine – you pick from our itinerary, and make the day one for the books.

Breathe underwater without needing any complicated certifications or the ability to swim, with this exciting SeaTrek excursion in St. Maarten. Don the air-fed helmet and breathe normally as you descend into the ocean—almost like a fish! Slowly walk across the ocean floor and witness vibrant tropical schools of fish and corals. There's also time to enjoy traditional snorkeling before or after the SeaTrek.

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!

Take in what St. Maarten has to offer on this island sightseeing tour. Covering natural and historical highlights, enjoy stops at the Moses Walk, Maho Beach, and the island capital, Marigot. Learn about the island’s heritage from your guide as you drive to each location. Perfect for visitors who want an introduction to St. Maarten, as well as those with limited time on the island.

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.