Racing alongside Olympic sailors

  It’s a fact unknown to most people outside of yacht racing circles that the Cayman Islands has been represented in major sailing regattas around the world, winning an impressive number of trophies during the past few years.  

Powerplay, a TP52 racing yacht with sail number CAY52, owned and crewed by Cayman resident Peter Cunningham, has raced in some of the biggest regattas in the northern hemisphere.  

It was only after he sold his business, at nearly 70 years old, that Mr. Cunningham decided to pursue his next venture. “I wanted to have a boat and do the big boat series,” he said.  

This was a world away from racing dinghies or J22s. Racing big boats, he said, is like the Grand Prix of sailing – and he wanted to buy a racing yacht and enter the big five: the Key West regatta, the New York Yacht Club regatta, Cowes Week, Les Voiles de St. Tropez and the California Big Boat series.  

Although Mr. Cunningham had been sailing since he was a child, racing at this level was a whole different ball game. These regattas are where the best sailors in the world come together and compete on boats that are the yacht-equivalent of a Formula One race car – and Mr. Cunningham wasn’t planning to stand back and observe. He was going to be part of the team and he wasn’t going to let his age get in the way.  

After chartering boats to race in a few regattas, Mr. Cunningham started looking for a boat to purchase. He had seen TP52s (a class of yacht used for competitive racing) in Key West, but wasn’t initially keen on this type of boat. He wanted to be an active crew member, but, despite being fit and agile for his age, he wasn’t entirely confident about crossing the 15-foot space from one side of the boat to the other when tacking or jibing.  

“You need to be pretty athletic to get across those things and it’s a really powerful boat,” he said. The issue is if you fall over, he said, something that can happen to anyone.  

However, having given it a few tries, he found he was nimble enough to handle the boat, and so he put in an offer for, and subsequently purchased, a TP52. He painted a stingray on the hull, registered sail number CAY52 and named it Powerplay. In the 18 months he raced on PowerPlay, he only fell once.  

One of his objectives in entering the big boat series, was to find out what it was like, Mr. Cunningham said. And what he found, besides the speed and the competition, the sun and the wind, was the value of finely-tuned teamwork. 

“A lot of it is about anticipating,” he said. “You can’t wait for the communication. It’s almost like the orders are a confirmation that you’re doing the right thing. 

“To start with it’s petrifying because this is a major competition and I’m not a world class sailor,” he said of racing alongside the best in the world. “I’m not an Olympic champion, and these guys were really, really good.”  

His crew included five world champions, three Olympic medallists, and veterans of the America’s Cup. But if he wanted to sail, he just had to do it.  

“If you’re part of the team, you’ve got to perform,” he said. “At the beginning, I didn’t say very much. They told me what to do and I did it. After a few races they said, ‘Hmmm, you need to start talking.’ They began to feel confident that I knew what I was doing. 

“By the last two regattas, I was really a full part of the team and communicating,” he added. “Actually, that was one of the reasons we did better.” 

By better, he means that Powerplay placed first in the Rolex Regatta in St. Thomas, Cowes Week in the United Kingdom and Les Voiles de St. Tropez in France in 2012. The team also placed second in a number of other races. 

Despite the impressive results, Mr. Cunningham remains self-deprecating, crediting the crew with their success.  

“No way am I as good as some of the guys who sail professionally – it’s impossible” he said. “They’ve had incredible experience and I was not going to be able to match that, so you don’t try. But what you hope is that the team can make up for it.” 

Even if the few did cover for him in some senses, in his own way Mr. Cunningham’s participation has been valuable to the crew.  

“The fact they took someone like me, who was – for this kind of boat – a complete novice and was able to get to the stage where we won some big regattas – that’s going to do very well on their resumes,” he said. “For them, it’s a positive thing in their careers.” 

Nowadays, Mr. Cunningham said, one can make a career not only out of racing yachts, but boating in general – something that was not possible a generation or two ago. And with Cayman’s seafaring heritage, perhaps among the next generation of Caymanians there are some world-class sailors in the making.  

Mr. Cunningham said his plan was to dedicate two years to racing big boats. Those two years are now up, and today you are more likely to find Mr. Cunningham sailing around the North Sound. Having had a taste of big boat racing though, he plans to be back on the race circuit before too long – just as soon as his next business venture is up and running. 


With a stingray painted on the hull and sail number CAY52, Powerplay has represented the Cayman Islands in major regattas around the world. – Photo: Submitted

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