Random Wind
The island's most fun day sail with a Tarzan swing and all-inclusive everything
Why Go
Random Wind has earned its reputation as one of the top day sail experiences in St. Maarten, and it's not hard to see why. Their 52-foot luxury catamaran takes a maximum of 30 passengers — small enough to feel personal, big enough to have a real party. The all-inclusive package means food cooked fresh onboard, open bar, snorkeling gear, paddleboards, and their famous Tarzan rope swing into the Caribbean. It's the kind of day that becomes the highlight people mention first when they get home.
The Experience
From the moment you step aboard, the crew sets a tone that's fun without being overbearing. The catamaran is comfortable and well-maintained, with plenty of cushioned lounging space. You'll sail along the coast with stops for swimming, snorkeling in clear water, and beach time. The Tarzan swing off the boat is the signature moment — adults and kids alike line up to launch themselves into the sea. Lunch is cooked right on the boat and is surprisingly good for a sailing trip. The open bar keeps flowing throughout, and the crew genuinely seems to enjoy what they do.
What to Try
The Paradise Day Sail is the flagship experience — book that one. It covers everything: sailing, swimming, snorkeling, the rope swing, paddleboarding, a full meal, and drinks. If you have a larger group or want a private experience, their custom charters accommodate up to 30 guests and let you set the itinerary. The sunset sail is a more relaxed option if a full day feels like too much.
Insider Tip
Book at least a few days in advance during high season — the 30-person cap means they sell out. Bring reef-safe sunscreen and a waterproof phone case. The morning departure gives you calmer seas than afternoon options. If you're prone to seasickness, take medication before boarding — the catamaran is stable, but the open ocean is still the open ocean.
The Practical Stuff
Departures from Simpson Bay area. All-inclusive pricing puts this in the $$$ range, but you're getting a full day of food, drinks, and activities. Book online or by phone. Bring a towel, sunscreen, and swimwear. Snorkel gear and water toys are provided. Credit cards accepted for bookings. Plan for a full-day commitment — morning departure to late afternoon return.
Pair It With
- Buccaneer Beach Bar Guide — Wind down after your sail with sunset drinks on Kim Sha Beach
- Pineapple Pete Guide — Dinner with live music after a full day on the water
- Simpson Bay Resort, Marina & Spa Guide — Stay marina-side for easy access to the departure point