SV Random Wind Too Has Arrived: Second Catamaran Meets Growing Demand
Catamaran cruises along Sint Maarten's coastline are one of the most popular ways to spend a day on the Caribbean Sea — and Random Wind Charters has been a cornerstone of that experience, having carried over 160,000 guests since it began sailing.
Demand has grown so strong that even outside peak winter season, guests now need to book weeks in advance to secure a spot. That surge is why Random Wind has invested in a second vessel: the Random Wind Too.
Catamarans are the preferred platform for day charters because their double-hull design offers more stability than a standard monohull. Random Wind brings its own twist to that formula: neither of its boats was purpose-built for the charter trade. Both started as cruising yachts, later modified for day-guest comfort — and both are homes to full-time crew living aboard.
Those modifications include a comfortable, non-nautical restroom and an onboard boutique offering souvenirs and gifts, giving each cruise a personal touch beyond the standard charter experience.
Both boats also share Random Wind's signature feature: the Tarzan Swing, a highlight guests talk about long after their trip — and often the reason they come back for a second sail.
Good to Know for Families
| Kids Welcome | All ages. Life vests provided in all sizes. |
| Doing It Solo? | We've had many single parents on board. The crew is used to helping out, and the boat has plenty of space for kids to move safely. |
| Food | Lunch included. Chicken satay, rice, salad. Let us know about dietary needs when booking. |
| Pick-Up Points | Most guests meet at SkipJack's Seafood Grill in Simpson Bay. Cruise ship guests can instead be picked up at Bobby's Marina in Philipsburg — let the crew know when booking. |
| Capacity | Up to 30 guests, licensed for more. Spacious, not crowded. |
Location of the Simpson Bay Pick-Up Point at SkipJack's Seafood Grill
Location of the Philipsburg Pick-Up Point at Bobby's Marina for Cruise Ship Passengers
Planning a Celebration Instead?
Random Wind also offers Private Charters — the whole catamaran to yourselves, up to 30 guests, perfect for weddings, birthdays, anniversaries, or family reunions. Runs 10am–3pm, extendable into the evening for $100/hour, with custom food and drink requests available.
