A Legendary Sail

Even a celebrated sailor like Gary Jobson runs into trouble sometimes. In this case, I was on board, just trying to keep up.
Gary Jobson
To this day, National Sailing Hall of Famer Gary Jobson is one of the most vocal and influential voices furthering the sport of sailing. Herb McCormick

Gary 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?

We never did make it to the first lighthouse (did I mention the weather?), but Jobson wanted me to have a spell on the tiller under the kite, and expertly set it from the cockpit, which was cool. “I do foredeck, but not on the foredeck,” he said. 

And man, did Whirlwind ever haul the mail, slicing downwind in double-digit fashion as I steered for dear life. I enjoyed a lot of great sails in the past year, but none better.

It was all going swell until we rounded Thomas Point Lighthouse and turned back upwind. The breeze had not eased off. We took a couple of waves aboard that pretty much filled the cockpit. The motor’s battery was swamped and fried, along with the bilge pump. There was much bailing. 

A crew of midshipmen on an Academy race boat idled alongside for a bit to make sure we were OK. They of course had no idea who I was, but I’m sure they realized: “Whoa. That’s Gary freaking Jobson.” Amid the chaos, it was pretty amusing. 

There was just one last bit of drama. Under sail on the last wisps of the fading northerly (at last!), we eked through the drawbridge at the 4:30 opening. Gary had been counting down the minutes from a quarter-mile out, and I was sure we’d be late, but I’m certainly not in any Hall of Fame. The bridge’s rails were of course lined with stranded refugees from the Annapolis Sailboat Show waiting to move, and I have no doubt that at least a few made the same “Is that who I think it is?” connection as the middies. 

Had the tender left the bridge open for a few extra ­moments as a favor as we passed through? Perhaps. “I’ll bring up another case of Heineken tomorrow,” Jobson said. 

As a sailor, I’ve been a lucky lad to knock off more than a few of my bucket-list voyages. And now I have another. I’ll always be able to say that I sailed through the Spa Creek Bridge on a windy day with a legend.