Racing an America’s Cup Sailing Boat Through the Caribbean

I’ll be honest, most cruise ship excursions bore me. It just seems like there are always too many people that are being shuffled into large buses to an activity that sounded adventurous in the brochure, but instead turns into the equivalent of a kiddie ride at the local fair.

That was not the case today.

We were disembarking our overindulgent Celebrity Cruise on the Caribbean island of St. Maarten to embark on a bit of a sleeker ride.

The adventurous afternoon excursion would have us sailing aboard an authentic America’s Cup regatta yacht as a crew member, competing in a light-hearted race where the only reward was bragging rights, and possibly a little extra rum punch.

The America’s Cup is a trophy that goes to the winner of a heated race between two of the best sailing boats, the defender and the challenger. America has the title of the longest winning streak in the sport, defending the cup 24 consecutive times, until 1983 when Australia was triumphant in breaking their series of victories.

The U.S. won the America’s Cup back in 1987.

For this cruise outing a group of us would be racing three retired America’s Cup regatta yachts: the Canada II, True North and Stars & Stripes.

All the teams, who were made up of mostly Americans, wanted to ride on the Stars & Stripes since it was the ship responsible for winning back the trophy from Australia after they had broken the U.S. winning streak. But, my group lost our chance after a fierce game of rock-paper-scissors. Damn you scissors.

We ended up  on True North, a sailboat built by Canadians.

Prior to boarding everyone was assigned a position based on their desired activity level.

Did you want this to be a leisurely sail or more physically demanding ride?

I chose the latter of the two and was appointed as a primary grinder, others were delegated to be main grinders and winch operators. Those who wanted a more relaxing position were assigned to tasks like being the bartender — not a bad gig in my eyes.

The four primary grinders, including myself, sat towards the front of the boat. We would be operating a pedestal with handle bars that protruded from the ground. It looked like simplistic machinery, but this equipment and position is the heart of the boat, it powers the sails and boom.

It is a physically demanding job.

When the captain yelled, “primary grinder, gear one, ready” we would get into position by grabbing onto the handles and placing our feet shoulder width apart.

When he said “Go”, the four of us would start cranking as fast as we could. Sometimes the rigorous rotation would last mere seconds and other times it left us pumping until our teeth were clenched and biceps started to ache.

Our efforts assisted the boat in turning in the direction needed to stay on course.

We raced through the choppy waters of Great Bay for three thrilling laps. The sails blew in the wind, water splashed onto the boat when it leaned to the side and our teams voices got louder with encouragement as we were trying to catch our competitors.

“We are gaining on them!” the captain yelled. And we pumped harder, but our attempt was futile.

In the end we came in third, otherwise known as last.

Both Stars & Stripes and Canada II crossed the finish line before us, but not for lack of effort. Either way, it was an incredible afternoon well spent. It turned out to be a great addition as one of the top things to do before you die.

This America’s Cup Sailing Regatta is an excursion option when sailing to St. Maarten with Celebrity Cruises. You can also book direct through 12 Metre Challenge who sail in either St. Maarten or Cozumel.

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