Sailing with a Legend

Even a celebrated sailor like Gary Jobson runs into trouble sometimes. In this case, Cruising World’s Herb McCormick was on board, just trying to keep up.

To this day, National Sailing Hall of Famer Gary Jobson is one of the most vocal and influential voices furthering the sport of sailing. Jobson motioned for me to step aboard his pretty, impeccable C.W. Hood 32, Whirlwind. Before anything else happened, and plenty was about to, he offered a thought.

“I’m a lot different than a lot of professional sailors,” he said, referring to his peers in the America’s Cup and the upper strata of inshore and offshore sailboat racing. “I really like to sail.”

Boy, does he. Jobson is a winning member of the 1977 America’s Cup and historic 1979 Fastnet Race crews; an author, filmmaker, television producer, award-winning TV commentator and fellow Cruising World editor-at-large; and a member of the National Sailing Hall of Fame who still regularly competes in major regattas. He annually gives more than 100 lectures for yacht clubs and other venues. On top of all that, he also takes several dozen lucky folks for daysails on the Chesapeake Bay each year from his home in downtown Annapolis, Maryland.

And now, it was my turn.

Given the sporty forecast for that Sunday afternoon this past October, a cold northerly gusting over 25 knots was already raking the bay, I was prepared for a cancellation, but Jobson waved me off. “It’s supposed to ease off later,” he said.

And with that hopeful ­sentiment, Whirlwind was eased from her lift into the drink and we were off. It was a short motor under the boat’s silent electric auxiliary from its Spa Creek berth to the ­nearby drawbridge for the 12:30 opening. Jobson mentioned that he maintains fine relations with its tenders. “Good guys,” he said. “I drop off a case of Heineken every year to show my appreciation.”

With the bridge negotiated, up went the mainsail, and as we fairly sizzled past the seawall fronting the US Naval Academy, Jobson laid out the day’s itinerary. It would be a tight reach up and under the Chesapeake Bay Bridge to the Sandy Point Lighthouse, a spinnaker run to the Thomas Point Lighthouse, and then a beat back to the city.

Given the conditions, this seemed quite ambitious to me, but I was sailing with Gary Jobson. What the hell did I know? – Full story