Sailing Charters in St Martin / St Maarten
- Trusted by travelers
- Secure deposit booking
- Concierge-level support
- Trusted by travelers
- Secure deposit booking
- Concierge-level support
Our Sailing Charters
Discover the magic of St Martin / St Maarten aboard a private sailing charter. Choose from spacious catamarans, elegant monohulls, and fast, stable trimarans — all captained by trusted local crews. Whether you prefer a relaxed half-day sail, a full-day island adventure, or an unforgettable sunset cruise, sailing offers the most peaceful and scenic way to explore the Caribbean.
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Island
Experience
Trip Length
Boat Type
Departure
Price
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FULL DAY — St Maarten Catamaran Cruise
Total: $ 1560
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HALF DAY — SXM Catamaran Adventure
Total: $ 1040
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SUNSET — SXM Sunset Catamaran Cruise
Total: $ 960
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FULL DAY — Tintamarre Sailing Experience
Total: $ 1550
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HALF DAY — SXM Caribbean Breeze Sail
Total: $ 1275
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SUNSET — SXM Afternoon Glow Sailing Cruise
Total: $ 1150
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SUNSET — SXM Golden Hour Sailing Cruise
Total: $ 650
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FULL DAY — SXM Coastal Sailboat Charter
Total: $ 1700
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FULL DAY — SXM Luxury Catamaran Day Sail
Total: $ 1800
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FULL DAY — St Martin Catamaran Sailing Trip
Total: $ 1248
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HALF DAY — SXM Catamaran Sailing Experience
Total: $ 828
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SUNSET — SXM Sunset Sailing Cruise
Total: $ 662
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HALF DAY — Whale Watching Experience
Total: $ 1488
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Pay just the deposit online today. Your remaining balance is paid directly to the captain on the day — cash or card accepted.
Questions? Message us on WhatsApp or email bookings@explr.sx
How it Works
Pay a small deposit now. Settle the balance with your host on the day.
Step 1:
Choose Your Experience
Step 2:
Reserve with a Deposit
Step 3:
Enjoy Your Trip
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Frequently Asked Questions
What is included in a sailing charter?
Most charters include a licensed captain, fuel, onboard drinks (water, sodas, juices), snorkeling gear, shaded seating, music system, and safety equipment. Many boats also provide paddleboards, floats, and fresh-water showers.
Most charters include a licensed captain, fuel, onboard drinks (water, sodas, juices), snorkeling gear, shaded seating, music system, and safety equipment. Many boats also provide paddleboards, floats, and fresh-water showers.
A catamaran has two hulls, offering maximum stability and space — ideal for groups and families. Monohulls provide a traditional sailing experience with elegant movement on the water. Trimarans have three hulls, combining comfort with speed and outstanding smoothness while underway.
Yes. Sailing charters are highly flexible. Your captain will recommend the best route based on wind and sea conditions, but you choose how long to stay at each stop and what type of experience you want.
Absolutely. Catamarans and trimarans are extremely stable, with comfortable seating and shaded areas. Crews are experienced in helping families, and routes can be adapted for calm waters and shorter travel times.
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Discover 90 + experiences across St Martin, St Maarten, Anguilla & St Barths.
Why Choose a Sailing Charter in St Martin / St Maarten?
Sailing is one of the most iconic experiences in St Martin / St Maarten. With calm trade winds, turquoise water, and dozens of sheltered coves, the island offers ideal conditions for catamarans, trimarans, and classic monohulls. A private sailing charter gives you the freedom to explore the coastline at your own pace — stopping to swim, snorkel, paddleboard, or relax on deck while your crew handles everything.
Unlike motorboat charters, sailing is quiet, smooth, and environmentally friendly. You’ll glide across the water powered by the wind, enjoying wide open decks, shaded seating, and plenty of space for groups, couples, and families.
What Can You See on a Sailing Charter?
Most itineraries include a mix of secluded bays, snorkeling reefs, and calm lagoons. Popular stops include Tintamarre (for sea turtles), Pinel Island (for paddleboarding and beach bars), Happy Bay (for snorkeling), Baie Longue, and the cliffs of Creole Rock. Catamarans and trimarans offer incredible stability, making them ideal for full-day trips or groups with kids.
Types of Boats Available
Catamarans: Spacious, stable, perfect for groups & families
Monohulls: Traditional sailing feel, great for couples and adventure lovers
Trimarans: Fast, smooth, and extremely comfortable for coastal cruising
Each boat type offers shade, seating, freshwater showers, onboard coolers, snorkeling gear, and experienced captains who know the best routes based on weather and wind.
Half-Day, Full-Day & Sunset Options
Short sailing sessions are great for travelers with limited time, while a full day at sea lets you discover multiple locations and enjoy relaxed beach time. Sunset sails are one of the most romantic experiences on the island, offering golden light, calm seas, and unforgettable views of the St Maarten coastline.
Who Are Sailing Charters Best For?
Couples seeking romance
Families wanting a smooth, safe, spacious boat
Groups celebrating a birthday or reunion
Travelers who prefer peaceful cruising over speed
Anyone looking for premium comfort and scenery
Whether you want adventure, relaxation, or a mix of both, a private sailing charter is one of the best things to do in St Martin / St Maarten — offering flexibility, comfort, and breathtaking Caribbean views.
