Surely every amateur sailor’s dream is to race with a yachting star. What could you learn from an Olympic Gold Medallist? What secrets of speed could you glean from an America’s Cup skipper? There’s one unique event that gives ordinary sailors the chance to find out – the annual Bitter End Yacht Club Pro Am Regatta, a week of racing and partying in the Caribbean sun.

This year’s Pro Am, the 23rd, started yesterday on the clear turquoise waters of the British Virgin Islands where the BEYC is idyllically situated. The skippers are a roll call of ‘rock stars’ – Paul Cayard, Ken Read, Keith Musto, Zach Railey, Anna Tunnicliffe, plus ‘wild card’ amateur Craig Albrecht. The Amateurs are guests at the Bitter End Yacht Club hotel, allocated to skippers by lottery each morning, and everyone gets a chance to sail with their most admired Pro by the end of the week.

Race one is sailed in a menagerie of local cruisers, a warm-up for the more intense competition of day two onwards in small matched keelboats. When my name came up to crew for Paul Cayard, America’s Cup veteran, winner of the 1998 Whitbread Round the World Race and runner up in the 2005-06 Volvo in Pirates of the Caribbean, I imagine the thrill was the same as for a club golfer having the chance to play a round with Tiger Woods.

I was curious to see how Cayard would manage a crew of mixed experience including serious racers, beginners, his daughter 19-year-old Allie Cayard, and me pointing a camera at him and quizzing him, all the while trying to get a Moorings 4000 charter catamaran – a luxurious craft literally designed for comfort rather than speed ­­- into racing mode.

Firstly, from the eight Amateurs aboard he picked a helmsman he knew was good from previous Pro Ams – Jim Durden, a keen Martin 242 sailor from Southern California. With the helm in good hands, Cayard allotted trimming spots to those who wanted them, and from then on focused totally on calling the start.  A couple of timed runs had us on the line right on the gun, in touching distance of rival Ken Read in an identical cat. Frankly, it was nail-biting. Jim the helmsman who was carrying out Cayard’s instructions to the letter, said, ‘it was one of the best executed starts of my life.’

The first leg was a run down the hilly coast of Virgin Gorda, contending with a current and lots of shifts, puffs and dead spots. Cayard’s eyes were everywhere. On the water, on the topography, on the sails, on the rest of the fleet.  Constantly talking to the helmsman, ‘Jimmy, bear off in this puff. There’s a nice solid puff here, take it down my friend!

Always looking ahead, ‘we’re going to get lifted’ he said. ‘How do you know’ I asked, ‘the wind will bend round that point’, he replied.

I asked Cayard whether he does much of the tactics when he’s helming a boat and he said, ‘the chess game is in the tactics. I’m doing it more and more. Look now, the boat in front has gone inshore on the straight track to the mark but there’s less wind in there. I’m willing to risk the extra hundred yards we’ll sail by staying out here in the breeze.’

We beat Ken Read, the multiple J24 world champion and second overall in last year’s Volvo race,  in leg one, and teased him a little over barbeque lunch at the beautiful Baths. But Read joked, ‘you watch out, I have something up my sleeve for the leg back.’

He did, a boat that would point! All the fine trimming in the world couldn’t get our cruising cat to go well to windward on port tack. Cayard continued to gently motivate the crew and call the wind and tactics but eventually groaned, ‘this is painful’.  In the end neither Cayard nor Read won the catamaran class, honours going instead to Tom Leweck on a Leopard 4500.

In the IC24 class Britain’s veteran Keith Musto beat the two young American Olympic gold and silver medalists Anna Tunnicliffe and Zach Railey, and the cruiser class was won by Brad Dellenbaugh.
Back ashore at the first of many parties the week has in store, I reflected on how Cayard does what he does. He stays calm, he looks out of the boat all the time, he’s constantly quietly instructing the helmsman and trimmers, he’s always anticipating what the wind’s going to do next. He’s always focusing 100% on the race. No doubt he has a touch of magic when he’s on the helm that defies analysis.

Over the rest of the week the skippers will be locked into intense ‘triple racing’, a hybrid of match-racing and team-racing. Very exciting for Amateur crews and spectators alike.