O Captain Your Captain

Don’t let a lack of sailing chops—or even a boat—stop you from experiencing the euphoria of racing along under spinnaker, wind whipping massive sails, another beautiful yacht eating your wake. Instead, leave it to pros like Tony Rey, a veteran of the America’s Cup, Olympics, Volvo Ocean Race and multiple Maxi campaigns (see above) and president of Cloud10 Racing in Newport, R.I. “We’ve set up boats and crews in two St. Barts Bucket Regattas,” Rey says. “One year, the client had zero sailing experience—and we won.”

Rey, who’s also one of the sport’s most sought-after trainers, is able to source the most advanced race boats for charter, such as the Super Maxi Leopard

3 (left), then assemble a professional crew and handle details like insurance, travel, logistics—even five-star accommodations. The skipper experience isn’t cheap; depending on the boat’s size and crew, the adventure can cost between $100,000 and $500,000. “Race boats that can win aren’t just sitting on the shelf,” Rey says. “You need to know what’s out there, then put together the right crew.”

Having started the business around 10 years ago to “open up sailing” to high-net-worth individuals, Rey has seen a range of clients and goals. “Some might bring family and friends who serve as crew,” he says, while

“others do post-race charters with just the captain, chef and a few of the yacht’s crew, so they can see the Med or Caribbean with their families.”

An adrenaline-fueled racing experience is sure to be the memory of a lifetime, but of course victories can’t be guaranteed, especially sailing against fiercely competitive owners who have assembled their own highcaliber crews. But dreams do come true—even if, as Rey says, the novice’s St. Barts win was something of a fluke. “It was a big, stable yacht and the racing was mostly straight-line sailing, without a lot of maneuvers,” he says. “We taught him as we raced. For him, it’ll always be a dream event.”