Sailing Charters St Martin / St Maarten – Catamaran, Trimaran & Monohull Tours

Sailing Charters in St Martin / St Maarten

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    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

    Duration

    Max Guests

    Catamaran sailing off the coast of Sint Maarten surrounded by crystal-clear blue water

    FULL DAY — St Maarten Catamaran Cruise

    Total: $ 1560

    6 h

    17 max

    Catamaran

    Simpson Bay

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    Aerial view of a red-and-white catamaran anchored off Maho Beach in turquoise waters of St Maarten

    HALF DAY — SXM Catamaran Adventure

    Total: $ 1040

    4 h

    17 max

    Catamaran

    Simpson Bay

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    Golden Caribbean sunset viewed from a catamaran deck with guest admiring the horizon

    SUNSET — SXM Sunset Catamaran Cruise

    Total: $ 960

    3 h

    17 max

    Catamaran

    Simpson Bay

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    Couple after snorkeling at Tintamarre on Sint Maarten's trimaran tour

    FULL DAY — Tintamarre Sailing Experience

    Total: $ 1550

    5 h

    16 max

    56 ft Trimaran

    Simpson Bay

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    Guests cheers a glass of wine onboard private charter st maarten

    HALF DAY — SXM Caribbean Breeze Sail

    Total: $ 1275

    5 h

    16 max

    56 ft Trimaran

    Simpson Bay

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    Gold skies and glow SXM sunset charter on a trimaran

    SUNSET — SXM Afternoon Glow Sailing Cruise

    Total: $ 1150

    4 h

    16 max

    56 ft Trimaran

    Simpson Bay

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    Guests marvel at glorious sunset onboard trimaran private charter SXM

    SUNSET — SXM Golden Hour Sailing Cruise

    Total: $ 650

    2 h

    16 max

    56 ft Trimaran

    Simpson Bay

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    Private sailboat charter cruising along the St Maarten coastline

    FULL DAY — SXM Coastal Sailboat Charter

    Total: $ 1700

    7 h

    10 max

    44 foot Monohull

    Cole Bay

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    Private catamaran anchored in a sheltered bay in St Maarten

    FULL DAY — SXM Luxury Catamaran Day Sail

    Total: $ 1800

    7 h

    11 max

    44 foot Catamaran

    Cole Bay

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    Catamaran cruising in crystal-clear turquoise water near luxury villas in St Martin

    FULL DAY — St Martin Catamaran Sailing Trip

    Total: $ 1248

    8 h

    12 max

    38 ft Catamaran

    Orient Bay

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    Catamaran sailing along St Martin’s coastline with tender boat behind

    HALF DAY — SXM Catamaran Sailing Experience

    Total: $ 828

    5 h

    12 max

    38 ft Catamaran

    Orient Bay

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    Champagne and glasses on the bow of a catamaran during a sunset cruise

    SUNSET — SXM Sunset Sailing Cruise

    Total: $ 662

    3 h

    12 max

    38 ft Catamaran

    Orient Bay

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    Humpback whale breaching the surface during a whale watching tour near St Martin

    HALF DAY — Whale Watching Experience

    Total: $ 1488

    4 h

    12 max

    Winter Only

    Orient Bay

    See Details

    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.

    Guest Reviews

    Our island activities turn dream days into real memories — hear from guests who’ve lived it!

    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.

    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.

    Need Help Choosing a Charter?

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    Not Sure Which Charter? We’ll Guide You

    Tell us a little about your trip, and we’ll match you with the best option.

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