Mike Hennessy is taking time off from his job as managing director of capital markets at Morgan Stanley Smith Barney LLC for a high-speed jaunt through the Graveyard of the Atlantic.
Hennessy, 45, is scheduled to steer his 40-foot racing yacht, “Dragon,” out of Charleston Harbor in South Carolina at 6 p.m. local time today in a race against 14 other Class 40 sailboats to New York in the first leg of the Atlantic Cup. The regatta ends in Newport, Rhode Island, on May 27.
In the 640-mile (1,030 kilometer), 80-hour leg to Manhattan, Hennessy and his crew, yacht designer Merfyn Owen, must navigate the waters of the Graveyard off North Carolina’s Cape Hatteras, where severe weather and shoals have combined to sink hundreds of ships since the 1500s. Winning the race, in which he placed second last year, also requires a good finish in a shorthanded leg up the coast and a crewed inshore regatta off Newport.
“Sailing offers a lot of really great challenges,” Hennessy, who works for Morgan Stanley (MS:US) in Purchase, New York, said in a telephone interview. “It requires you to have a certain ability to manage information flow. You’re dealing with a tremendous amount of data from the wind, the environment, navigational choices. It requires a great deal of self-reliance. And it requires a wide knowledge base to do it safely.”
This year’s Atlantic Cup includes the largest fleet ever assembled in the U.S. for the Class 40, a boat designed in France in 2005 to make solo and shorthanded ocean racing accessible to amateur sailors, says Owen, who designed Dragon at his U.K.-based Owen Clarke Design LLC.
Class 40s retail for about $260,000, with top speeds of about 20 miles an hour (32 kph).
The other teams include France’s Halvard Mabire, whose resume includes five around-the-world and 32 transatlantic races, and the U.K.’s Peter Harding, who won the Fastnet Race in 2007 and the Class 40 championship in 2008.
Hennessy and Owen said they like their chances. They won the double-handed division of the Newport-Bermuda race in 2010, and Owen said that sailing together has helped both.
“It’s a good way of transferring knowledge, and I get feedback coming the other way,” Owen said in a telephone interview from Charleston. “The whole class was designed for non-pro sailors. They’re exciting, but not impossible to handle.”
Hennessy grew up on the water in California, Rhode Island and Connecticut. He rowed in college and enjoyed meandering from harbor to harbor along the New England coast in a 35-foot yacht. One summer, he said, he tried the 190-mile Around Long Island Regatta and “decided to start pushing myself a bit harder.” He got into racing shorthanded by default.
“I started out in fully crewed races, then pretty rapidly figured out that it’s a lot easier to get ready to race if you don’t have to find a crew,” Hennessy said.
He sailed alone to Bermuda to see if he liked it, then raced single- and double-handed for a few years. By 2006, he’d reached the potential of his racer-cruiser hybrid boat, decided to commit to distance racing and commissioned the boat from Owen.
Hennessy spent 2008 sailing that around his home port of Mystic, Connecticut. By 2009, he was doing local regattas, then the Newport-Bermuda race. In 2011, he finished second in both the Transatlantic Race and the Atlantic Cup.
“I started out very, very carefully,” he said. “It was a very new experience for me. It was definitely a steep learning curve, but also a lot of fun.”
Grown to Love
He’s grown to love what initially terrified him about the boat -- its envelope’s-edge combination of performance, power and speed.
Hennessy spent weeks prepping the boat in Charleston, laying in supplies and studying the route. From Charleston, he and Owen will round North Carolina’s Outer Banks, pass Norfolk and Virginia Beach, and head up the Maryland, Delaware and New Jersey coasts.
“We’ve got to decide where to enter the Gulf Stream and how close to cut it to Cape Hatteras,” Hennessy said, referring to the warm Atlantic Ocean current that runs up the East Coast of the U.S. and Canada. “If the weather system is going northwest, the seas get really heavy there.”
Owen said he expects a tactical race with shifting wind patterns, before a sprint from New York to Newport. The inshore races in Newport will be key, he said. For those, Hennessy has Chris Museler, who won nine U.S. Sailing championship medals from 1998 to 2009, prepping the crew.
For now, the two men have to get to New York, taking turns at the helm, handling the large square-top mainsail and even sleeping and eating. The sprint from just off Ellis Island in New York Harbor to Fort Adams in Newport begins May 19.
“It’s some beautiful sailing and also insanely challenging,” Hennessy said. “But you always talk about your bucket list, and it’s pretty cool to do it.”
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