I Took a 4-Year-Old on Random Wind. Here’s What Happened.

“Daddy, I had a great day on the boat,” said my four-year-old son before his head hit the pillow and he was fast asleep.

We’d spent the day on Random Wind, a 52-foot catamaran available for day cruises around St. Maarten. This isn’t a purpose-built floating party platform. Random Wind began life as a genuine luxury sailing yacht. She’s been thoughtfully adapted for day charters, but she’s kept the character and elegance of a real cruising cat. First mate Anna Holness actually lives aboard and runs the boat. If you’ve ever wondered what the cruising lifestyle really looks like, this is the genuine article — not a staged tourist attraction.

My son Mil is still learning to swim. He loves the water, but confidence hasn’t quite caught up with enthusiasm. And since this was his very first day on a boat in open water — and I was doing it as a single dad — I wasn’t entirely sure how he’d react once land disappeared behind us.

The adventure starts before you board

Rather than boarding from a marina dock, guests meet at SkipJack’s Seafood Grill in Simpson Bay. From there, a tender carries everyone across the lagoon, slips beneath the famous Simpson Bay Bridge, and heads into Pelican Cove where Random Wind lies peacefully at anchor. Before we’d even stepped aboard, the excursion already felt like the beginning of a small adventure.

Melle, the hostess, served the first round of rum punch. For Mil, it was a make-believe one. Every excursion starts with a safety briefing. It has to be done, just like on an airplane — though airline crews rarely deliver theirs in bikinis. What struck me was how refreshingly practical it was. No liability-lawyer script. Just straightforward advice delivered with common sense.

Little Bay: First swim in the deep

Once everyone settled in, Scotty — the skipper who’s Australian, not Scottish — turned the boat east toward Little Bay. A squall was rolling in with a bit of headwind. Mil decided the trampoline at the bow was the premium spot. He was mesmerized by the gentle waves and the movement of the boat. He shared that spot with an athletic young lady who, later that day, would become the Tarzan Swing champion.

Little Bay is one of the best snorkeling reefs in St. Maarten. In the lee of Fort Amsterdam — a not-so-memorable ruin on the bluff — Anna caught the permanent mooring and Random Wind settled in.

Snorkeling time

For Mil, this was his first swim in the deep ocean. While guests grabbed masks and fins, Mil found a swimming noodle in exactly the right color for his fashion sense that day. We went to the transom, down four comfortable steps, and jumped into crystal-clear water.

While guests snorkeled or floated with a noodle under one arm and a rum punch in the other, Mil picked up speed. We went under the hull, around the boat, and swam several circles around the snorkeling crowd. Before he was tired — I was — Anna announced that lunch was ready.

Chicken satay and “Don’t take my chicken!”

Random Wind carries up to 30 guests and is licensed for more, but there’s comfortable seating for everyone. No need to claim a spot.

Melle served a generous portion of chicken satay with rice and salad. I figured one plate would be plenty to share with my son. Juggling food, drinks, and a 4-year-old solo is always a bit of a circus, but he took the chicken and happily chewed away. In an unguarded moment, I reached for a bite. I was immediately scolded by a four-year-old: “Don’t take my chicken!” Everyone laughed, and I ate salad.

After lunch, my boy got a bit naughty. He took a chunk of bread and tossed pieces into the water. Small and mid-sized fish made the water boil, fighting over the tiniest crumbs.
I muttered “saltwater piranhas” to myself. Then I saw the shocked look from the person next to me and quickly clarified it was a joke.

Maho and Mullet Bay

Random Wind got underway westward, past the huge expanse of Simpson Bay and the bluff of Beacon Hill toward Maho Beach.

No, I don’t believe it was a coincidence. Right as we arrived at Maho and the famous end of the runway, an Air France jet was on final approach after a 10-hour flight from Paris.
Either the plane waited for Random Wind to show up, or Skipper Scotty timed it perfectly. The huge jet cleared the mast without a problem. It was still an impressive sight.

Next up: Mullet Bay. It’s one of the Caribbean’s picture-perfect beaches with white sand and water so clear you can see the bottom and the fish without goggles. Random Wind anchored in calm water.

While Melle kept the drinks coming, Anna prepared the big attraction: Random Wind’s unique Tarzan swing. If you’ve ever wanted to test your inner trapeze artist, this is the place.

Anna explained the procedure and safety. Then Melle gave us a demonstration, swinging far out over the sea and letting go at the highest point. Anna asked who wanted to try. A little arm shot up without hesitation. That was Mil. The reluctance was mine. I didn’t think his coordination was quite up to it yet.

To make up for it, we took his swimming noodle and watched the jumps from water level. The line of guests grew. Some unlikely candidates jumped with real style and got big applause from the spectators.
Two other catamarans anchored nearby. I could see their guests watching the Tarzan swing with a bit of jealousy.

Mil spotted big silver shadows hiding between the two hulls. It took me a minute to explain these weren’t “Baby Shark and family” but harmless tarpon.

The Tarzan swing did turn into a fun competition. And we had an undisputed champion: the young lady who’d shared the trampoline with Mil earlier. She did a flawless double roll, and everyone cheered.

The crew makes the difference

The mood on board was relaxed, friendly, and open-minded. Tim from Florida told me he comes to St. Maarten almost every year and always booked one of the well-established purpose-built charter cats. This was his first time on a real cruising yacht. I asked him if there’s a difference with Random Wind.
“A big one!” he responded, with both thumbs up.

Melle never got tired of serving drinks with a big smile, balancing the tray on the gently rocking boat.

Anna offered a life vest to Mil. He wore it for a short while but didn’t really need it. Even with 30 guests on board and me handling him solo, the crew always had a smile and a comforting word and never made me feel like I was in the way. Mil finally asked Anna for some cookies. She disappeared into her cabin and came back with Oreos. I suspect it was from her private stash.

Coming home

Soon, the yacht settled at her mooring in Pelican Cove, and the cruise came to an end. The problem started now. Mil wanted to stay on the boat. Even sleep there. I gave Anna the bad news that she now had a roommate. She took it in good humor and convinced Mil that the ride on the tender was great fun — especially because this time he could sit on the bow.

Within a few minutes, we were back at the dock at SkipJack’s, the restaurant now open for service.

“Daddy, I had a great day on the boat.”