SAILING IN ST. MAARTEN: America’s Cup Style


The weather was perfect.

The sun was high and the trade winds kept us from getting too hot as we prepared to board our tenders from the dock. I was here for another photo/video shoot with my team. We’d already experienced the excitement of soaring through the sky, thanks to the Flying Dutchman, and dipped below the waves on an incredible aquatic experience in Stingray City. I was next looking forward to joining our guests on a different kind of Caribbean activity, participating in mock-race on a world-class, America’s Cup-style yacht.

I had no idea how much fun I was about to have.

* * *

At the dock, our captain gave instructions for safety — this was number one with all that has to happen when crewing a racing yacht — then he taught us how to it works. After that, he assigned us to our different roles for crewing our vessel. Some guests were assigned to be “grinders,” which means they operated manual winches for controlling things like the boom and raising and trimming the sails. I was named the Team Captain (I’ll explain more of that in a moment) and put in charge of the mainmast. (There were also two or three deckhands on board to assist.)

We set out on our tender boats and, since I was Team Captain, I had the privilege of choosing our vessel. I selected True North IV. These 12 Metre Challenge sailing experiences in St. Maarten are on four beautiful racing yachts: Stars & Stripes 87, Stars & Stripes 86, Canada II and True North IV.

As Team Captain, I was charged with two main duties. First, despite my complete lack of sailing experience, I had to select our track on the course. Second, my role required me to motivate the team to victory — something I felt quite equipped for…until we got started. Apparently, my idea of egging our team on by trash-talking our opponents is a bit too nice. The more competitive guests schooled me on how to do it properly. They were almost too good at it!

The race started with a bang, albeit not a literal one. After pulling anchor, we set sail, and once both vessels aligned on the course, we were off! I’ve always enjoyed a good breeze and have always respected the power of the wind, from my time in California with the Santa Ana winds to my living in Florida, weathering tropical storms and more…but, experiencing the power of the wind as it pushes you through the surf, causing your vessel to heel as you cut across the bay is exhilarating in a unique way. It’s freeing and carries a romance with it, something from the past, when life had a different air of simplicity; a different time of discovery that steals your attention and reminds you how magical our world truly is. Then, the sea spray in your face brings you back into the moment as the wind shifts and the captain yells out the order to swing the mast and hold tight as you turn hard to port. We were, after all, in the middle of a race.

The shouting of orders by our skipper was key. We had to pay close attention to all the moving parts, taught ropes and sudden adjustments, reacting instantly to his orders to take the lead. It felt like something between a dance competition, a sparring match and…flying. We held the lead for most of the race, slicing through the surf, narrowly avoiding a collision with the competition and heeling so sharply that you weren’t sure if you’d fly off — it was thrilling!

I continued to trash talk and handle the main mast while our captain called out the orders. The grinding of the winch, the trimming of the sail, the constant vigilance and responsiveness required…I don’t know that any of us realized how hard the work would be. We held strong until the last leg of the race. The few-second delayed response to our captain’s order caused us to slip into second as we were overtaken by Stars & Stripes 87. It would’ve been crushing if we weren’t having such an incredible time.

We all felt it at the end. Some of us had rope burns and sore muscles…but it was worth it. I didn’t hear anything about the hard work involved over the next days of our cruise; only the same joy I’d experienced was reminisced about when running into my fellow teammates.

It was, without question, my favorite excursion in St. Maarten.

Sail around St. Maarten on a tropical escape with Regent Seven Seas Cruises. Experience the expansive, sapphire waters of the Carribbean on a voyage unlike any other.

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