I can state unequivocally that my favorite shore excursion (and that of my traveling companions, too) of our two-week Caribbean cruise aboard Holland America Line‘s ms Nieuw Amsterdam last winter took place in Philipsburg, Sint Maarten. There we spent a little over three hours on an authentic America’s Cup 12-metre yacht, helping to crew our vessel in a challenge (they’re not referred to as races in this context) on the waters of St. Maarten’s Great Bay.

The weather could not have been more perfect for such an activity: The sun was warm and bright, the wind blew steady but not too briskly, and the seas weren’t too choppy for smooth sailing.

On the open tender taking us out to the yachts, our gaggle of tourists, several of whom (including my husband and me) had never sailed before, were transformed into two crews of eight and given general instructions. While we all quickly became seriously committed to defeating the opposing crew, there was no lack of laughter and fun (and brewing excitement) as we approached the Stars & Stripes 87 (their vessel) and True North IV (ours).

Between 1907 and 1987, approximately 170 12-metre yachts were built, with only 100 now in existence. The yachts we would be sailing are around 70 feet long with 86-foot-tall masts and weigh in at 35 tons. The “12-metre” designation applies to a complex formula ships under that designation must meet.   The company operating this excursion, 12 Metre Challenge, boasts five of these boats in its fleet. Stars & Stripes 87 is among the most famous, having won back the America’s Cup for the United States from the Aussies in Fremantle in 1987.

Once we’d transferred from the tender to our vessel, we were introduced to the crew and given our assignments. (Those who didn’t wish to crew were put in charge of handing out liquid refreshments when called for and invited to sit back and enjoy the ride.) My friend Julie and I were “winch wenches,” and her husband, Paul, and Harry were grinders. We quickly learned that these duties required short, intense bursts of activity interspersed with stretches where we had time to take photos and observe our position in relation to our challenger. We encountered a glitch as we were preparing to get underway: As the main sail was raised, a large vertical tear was discovered in it, so the tender was called back and we were transferred to another yacht, the Canada II, which competed in the 1987 Louis Vuitton Cup. Its configuration was slightly different than the True North, but we quickly got oriented and headed out to test our mettle.

The time we actually raced against Stars & Stripes was perhaps only 30 minutes or so, but what a thrilling, exuberant time it was. Our skipper impressed me with his skill at commanding his rag-tag crew; calling out commands at just the right moment; and keeping a keen eye on our competition, the course and the conditions.   We tacked and maneuvered around the buoys, several times coming within just a few yards of the Stars & Stripes, close enough to be drenched in its spray and to throw some shade at its crew, and gaining the upper hand as we turned.

We would have been happy to spend the entire day on the water, but our challenge came to a close with, unfortunately, Stars & Stripes narrowly beating us out at the finish. We returned to shore and a rum punch party at 12 Metre Challenge’s gift shop, where we could purchase souvenirs and photos taken from a speed boat which had shadowed our excursion. Should I return to St. Maarten, you can be sure I’ll be signing up for another thrilling sail on one of those magnificent vessels!

— Patty Vanikiotis, associate editor/copy editor