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.

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.

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.

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.

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 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

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!

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.

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!

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.

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.

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.

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.

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.

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.

Our tours are designed to provide an unforgettable experience that highlights the beauty, culture, and history of our lovely island. This tour includes many stops that last between 15 and 20 minutes at the main attractions in both Dutch and French St. Maarten. Our knowledgeable and passionate guides are there to answer any questions, offer insights, and engage in conversations with our guests. We take pride in offering unique touring options that cater to different interests and preferences. Our mission is to create lasting memories for every traveler, and we strive to achieve this with every tour we offer.

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.

Our Tours are one of a kind. our goal is to give you the best experience tour you have ever gotten in your entire life. we focus on Fun, Education and more Fun. what makes us different then the rest tour companies is we make sure you leave St.Maarten with a big smile on your face. Our tours are educational and exploring the most amazing Island views and Beaches that St.Maarten has to offer. Our tour comes with free cold beverages throughout the entire tour.

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.