St Maarten is a slice of Caribbean paradise where sailing is practically a national sport. Its calm waters, steady trade winds, and picture-perfect coastlines make it an ideal place for exploring by boat. Whether you’re after a relaxed day lounging on a luxury catamaran or an energetic snorkeling adventure, the island delivers. We particularly love experiences like the 5 Hour Luxury Catamaran Day Sail in Sint Maarten, which offers a perfect balance of scenery, water sports, and local sights, including the iconic planes landing over Maho Beach. It’s a great way to enjoy the island’s famous approach to shore and the lively atmosphere of Philipsburg.
While all of these tours showcase the island’s best, each one caters to different interests and budgets. From intimate private charters to lively group excursions, there’s something for all. Now, let’s dive into each of the top sailing experiences in St Maarten to help you find your perfect match.
1. 5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix
At number 1, the 5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix earns top marks with a perfect 5.0/5 rating from over 900 reviews. This tour is outstanding for its combination of water activities, scenic coastline, and a lively atmosphere. You’ll start from Bobby’s Marina in Philipsburg and enjoy unlimited drinks, including cocktails, as you glide along the shoreline. The itinerary includes a brief sail past Maho Beach to watch planes land while unable to stop there but still getting a close-up view. The highlight is the final stop at Mullet Bay, where you can swim, snorkel, or simply relax on the boat. Guests love the friendly crew and delicious onboard lunch. This tour is ideal for those wanting a lively yet relaxed day on the water, with plenty of snorkeling and sightseeing. Bottom line: a top choice for first-timers and water lovers alike.
2. Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten
Number 2 on our list, the Private Full-Day Luxury Sailing Catamaran offers an exclusive experience for up to 8 guests. Priced at $1,700 per group, this tour lets you customize your day with stops at Little Bay and Tintamarre Island for snorkeling, paddleboarding, or just soaking up the sun. The crew’s attentive service is a standout, with rave reviews about the excellent lunch and unlimited drinks. What makes this tour special is the privacy—you won’t be sharing your adventure with strangers. It’s perfect for honeymooners, families, or groups wanting a more intimate, relaxed day on the water. The boat departs from a convenient location and offers a flexible itinerary tailored to your interests. Bottom line: a luxurious escape for those seeking privacy and bespoke service.
3. Tropical Catamaran Snorkeling & Sailing
Coming in at number 3, the Tropical Catamaran Snorkeling & Sailing is a 6-hour adventure perfect for active travelers. It combines sailing on both the French and Dutch sides, visits to top snorkeling spots, and a Caribbean buffet lunch with an open bar. The crew, praised for their professionalism and friendliness, takes you to prime locations like Maho Beach and secluded beaches for swimming and snorkeling. Guests love the lively atmosphere and the chance to see planes land overhead while floating in the water. The tour is best suited for those who want a full day of fun with a focus on marine life, quick dips, and a hearty meal. It’s a good value at around $132 per person, with flexible options for couples and friends. Bottom line: a lively and well-rounded day on the water.
4. Tropical Catamaran Snorkeling, Sailing And Beach Experience
Number 4 is the Tropical Catamaran Snorkeling, Sailing And Beach Experience, offering a 6-hour tour that emphasizes personalized service and secluded spots. The small group size ensures intimacy, while stops include less crowded beaches and snorkeling locations. The crew provides a buffet lunch and open bar, and the boat is equipped with snorkeling gear, dinghy service, and shade. Visitors rave about the friendly crew and the chance to explore untouched corners of the island. It’s ideal for travelers who want to escape the busy crowds, enjoy quality snorkeling, and relax with good food. At around $132 per person, the value for a peaceful, personalized day on the water is excellent. Bottom line: perfect for those seeking tranquility and authentic island scenery.
5. St Maarten Luxury Catamaran Full-Day Group Charter
At number 5, the Luxury Catamaran Full-Day Group Charter combines luxury and adventure over a 9-hour sail. With a four-course gourmet lunch and full open bar, you’ll cruise to spots like Long Bay, Happy Bay, and Tintamarre Island. Snorkeling, fishing, and paddleboarding are included, along with the chance to swim with sea turtles. Guests consistently rave about the delicious food and stunning scenery. This tour suits travelers wanting a generous, all-inclusive day with plenty of options for activity and relaxation. It’s more expensive at $245 per person but delivers a premium experience. Bottom line: a superb choice for those looking to indulge and explore in style.
6. No1SXM Day Sailing Experience in St. Maarten
Number 6, the No1SXM Day Sailing offers a 5.5-hour cruise on a trimaran, rated 5 stars with over 150 reviews. It departs from a convenient main road location and sails along the south coast, passing iconic sites like Maho Beach and Baie Rouge. The ride is smooth, with snorkeling gear provided, and the crew ensures a friendly atmosphere. Reviewers appreciate the balance of scenery, water sports, and relaxed sailing. It’s perfect for travelers interested in a shorter, comfortably paced day with good snorkeling and sightseeing. At $145 per person, it’s a solid value with excellent reviews. Bottom line: a reliable, enjoyable day sail for active and casual travelers alike.
7. Private Full-Day Catamaran Sailing Charter in St Maarten
Number 7, the Private Full-Day Catamaran is an 8-hour luxury experience for groups up to 15, costing $2,800 per boat. The boat is a 42ft Lagoon that offers spacious comfort, shade, and a customizable itinerary. Highlights include swimming, snorkeling, fishing, and exploring secret beaches like Tintamarre Island and La Samanna. Guests love the flexibility and the gourmet barbecue lunch served onboard. It’s ideal for special occasions, family reunions, or groups wanting privacy and personalized attention. The experience is high-end but offers full control over the day’s pace and activities. Bottom line: the best pick for private groups seeking a bespoke, luxurious day at sea.
8. Prickly Pear Catamaran Trip from St Maarten Including Lunch
Number 8, the Prickly Pear Catamaran Trip is an 8-hour cruise to Anguilla with a focus on snorkeling and beach time. You’ll stop at Prickly Pear Cay to snorkel among coral reefs and relax on its pristine beach. Included is a buffet lunch and open bar, making it a well-rounded day of water fun. Guests praise the friendly crew and the scenic stop at Mead’s Bay on the return trip. It’s perfect for those who want to combine snorkeling, island scenery, and a little adventure. The price is around $135 per person, offering good value for a full day in stunning surroundings. Bottom line: a solid choice for snorkeling and beach lovers.
9. Luxury Private Full-Day Catamaran Charter in St. Maarten & Saint-Martin
Number 9, the Luxury Private Full-Day Catamaran provides a fully personalized 7 to 9-hour journey. It includes stops at Tintamarre Island and La Samanna, with options to snorkel, swim, or relax as you see fit. The itinerary is flexible, and everything from gourmet lunches to unlimited drinks—including a full open bar—is customized. The reviews highlight its exclusivity and attentive crew. This tour suits travelers who want the utmost flexibility and privacy, especially for special celebrations or a leisurely escape. At $770 per person, it’s a premium, all-inclusive experience. Bottom line: perfect for travelers seeking exclusivity and tailored adventures.
10. Private St. Maarten Cruise – Hakuna Matata Catamaran
Number 10, the Hakuna Matata Catamaran is a 7-hour private tour designed for groups up to 8. It offers a flexible route with stops at beaches like Mullet Bay and Long Bay, snorkeling, swimming, and a homemade meal service with fresh sandwiches and grilled dishes. Reviewers especially enjoy the personal attention and the friendly crew. It’s ideal for families or couples wanting to avoid crowds while enjoying customized service. The price point is $1,830 per group, making it a high-end but intimate choice. Bottom line: a fantastic, customizable private charter for a relaxed day on the water.
11. Nude Naturist Catamaran Boat Luxury Charter in St Maarten
Number 11, the Nude Naturist Catamaran is a 9-hour adventure catering to open-minded travelers. It includes stops at Tintamarre Island and Long Bay, with all activities like paddleboarding, snorkeling, and swimming included. The experience is capped at 15 people, ensuring a private, relaxed atmosphere. The reviews highlight the quality of the food, drinks, and crew service. This tour is suited for adults comfortable with clothing-optional sailing and looking for a luxury, free-spirited day at sea. Costing $245 per person, it offers excellent value for a full day of indulgence. Bottom line: a unique, upscale experience for the adventurous.
12. Luxury Catamaran Private Charter in St. Maarten/St. Martin
Number 12, the Luxury Catamaran Private Charter features the sleek, new Lagoon 42 providing privacy, luxury, and flexibility. It includes stops at Tintamarre Island, La Samanna, and typically the French and Dutch sides, with snorkeling, paddleboarding, and fishing. The 9-hour itinerary can be personalized, and reviews mention the attentive crew and gourmet meals. It’s best suited for groups seeking an exclusive, high-end day with the ability to control every detail. At $598.75 per person, it’s a splurge but offers a boutique experience that’s hard to beat. Bottom line: ideal for travelers who want complete privacy and tailor-made adventures.
13. Catamaran Day Sail
Number 13, the Catamaran Day Sail is a 7-hour tour well-suited for those new to sailing or preferring a straightforward experience. It departs from Bobby’s Marina, with stops at Grand Case, Tintamarre, and Creole Rock. The crew provides snorkeling gear, and the boat boasts shaded seats and lounging nets. The included lunch at a local beach grill adds a touch of authenticity. Reviewers find it perfect for a relaxing, no-fuss day with plenty of swimming and sightseeing. At $125 per person, it offers an accessible way to explore the coast comfortably. Bottom line: a solid, casual choice for a full day on the water.
14. Best Sailing Catamaran, Beach and Snorkel – Cruise Ship Friendly
Number 14 features a 6-hour sailing and snorkeling cruise, ideal for cruise ship visitors or those with limited time. It offers a balanced itinerary with stops at Mullet Bay, Baie Longue, and Great Bay Beach, all with options for swimming, snorkeling, and relaxing on the boat. The crew keeps the atmosphere friendly, with a Caribbean buffet lunch and open bar. Reviewers appreciate the smooth ride and the chance to see planes land overhead at Maho Beach. At $122 per person, it’s a practical choice for those wanting a taste of sailing without sacrificing comfort. Bottom line: perfect for cruise passengers or short-term visitors.
15. Yacht YES DARLING – Private Boat St Martin, St Barth & Anguilla
Finally, the Yacht YES DARLING is an upscale 4-8 hour private experience on a 20m yacht. It offers visits to St Martin, St Barth, and Anguilla, with flexible stops and a luxurious interior. The boat is decorated in Italian style, boasting large sunbathing areas and shaded decks. The crew crafts bespoke itineraries with gourmet lunches, including barbecue and homemade dishes. Reviewers mention the elegant atmosphere and attentive service. It’s suited for groups celebrating special occasions or seeking a high-end, private escape. The price reflects its exclusivity, at over $6,400 for up to 12 people. Bottom line: a premier choice for those wanting ultimate privacy and luxury.
How to Choose Your Perfect Sailing Experience in St Maarten
When selecting a sailing tour, consider your budget, time available, and what kind of experience you desire. For a quick but scenic overview, the catamaran day sail offers a relaxed, easy approach. If privacy and customization are your priorities, the private full-day charters or the luxury private yacht are excellent options. Budget travelers will appreciate the snorkeling and sailing or best sailing cruise that balance affordability with fun. Remember, booking early is wise—these tours fill up fast, especially in peak season. Think about your fitness level and interests, whether it’s lounging with cocktails or snorkeling among colorful reefs, and pick accordingly.
Final Thoughts
From lively group sails to intimate private charters, St Maarten’s sailing experiences cover a broad spectrum of tastes and budgets. The 5 Hour Luxury Catamaran Day Sail on The Phoenix strikes a great balance for first-time visitors seeking variety and value, while the private luxury options are perfect for special occasions or those craving exclusivity. For budget-friendly fun and quick glimpses of the coast, the catamaran day sail or the best cruise for ship passengers are excellent picks.
Whatever your preference, these tours showcase the best of St Maarten’s lively waters and stunning scenery. To truly enjoy your trip, book early—these adventures are popular and tend to fill quickly, especially during peak seasons. Now, all that’s left is to choose your adventure and get ready for a memorable day at sea.