Random Wind — The 27-Year Legacy of Caribbean Day Sailing with a Tarzan Swing
A 52-foot sailing catamaran with 27 years of operation, a famous Tarzan swing, onboard galley cooking, and the 'Spirit of St. Maarten' crew.
Why Go
Random Wind has been sailing out of Philipsburg for 27 years — making it one of the longest-running charter operations on the island. The 52-foot sailing catamaran is famous for its Tarzan swing (a rope swing into the Caribbean from the deck), onboard galley-cooked lunch, and a crew that embodies what they call the 'Spirit of St. Maarten': warm, fun, and genuinely invested in your day on the water.
The Experience
Longevity in the charter business means something. Random Wind's 27 years and thousands of trips have produced a day-sail experience that runs like clockwork while feeling spontaneous. The Paradise Day Sail is the signature product: a small-group experience (max 30 passengers, often limited to 20) that includes sailing, swimming, snorkeling, stand-up paddle boarding, ocean kayaking, fishing, the famous Tarzan swing, and a lunch cooked in the onboard galley — not catered, not pre-made, but prepared fresh by the crew as you sail. The full open bar, comfortable cushioned seating, and all-inclusive gear (snorkel, kayak, SUP) mean you bring nothing but sunscreen and a swimsuit. The Tarzan swing has become Random Wind's unofficial logo: a rope swing mounted on the catamaran's mast that sends you arcing out over the water before dropping into the Caribbean. It is simultaneously thrilling and goofy, and it produces the kind of vacation photos and videos that go viral. Private charters for up to 30 guests allow customized adventures for events, celebrations, and groups. The crew's emphasis on sustainability, joy, and the spirit of the island shows up in the small details: the music choices, the cocktail suggestions, the way they make sure the quiet snorkelers and the Tarzan swingers both have the day they wanted.
What to Try
Book the Paradise Day Sail for the signature Random Wind experience. Jump off the Tarzan swing at least once — even if heights make you nervous, the crew will talk you through it. Try the stand-up paddle boarding during a calm anchoring stop. Eat the galley-cooked lunch with appreciation — onboard cooking is a dying art in the charter industry.
Insider Tip
The Tarzan swing photos are best taken by someone on the boat using the zoom on a phone or camera. The crew is used to being asked to photograph the moment and they know the right angle. Ask before you swing.
The Practical Stuff
Departing from 26 Juancho Yrausquin Boulevard, Philipsburg, Dutch side. Vessel: Random Wind (52ft sailing catamaran). 27+ years operating. Paradise Day Sail: max 30 guests (often limited to 20). Private charters: up to 30. Activities: sailing, swimming, snorkeling, SUP, kayaking, fishing, Tarzan swing. All-inclusive: galley-cooked lunch, full open bar, all gear. Hours: Mon-Fri 9 AM - 5 PM. Price range: premium ($$$).
Pair It With
- Great Bay Express Guide — Same Philipsburg marina for a St. Barths ferry trip on a different day
- Aziana Guide — Philipsburg dining near the marina after a day sail