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Back in the early ’80s, before I earned my journalism degree, when I was a passionate sailor fueling my habit tending bar in Boston, a magazine then called Yacht Racing and Cruising placed an ad for an entry-level editor. I sent a letter and resume—thin as it was then—and the editor invited me down to Connecticut for an interview. At the time, I’d had little interviewing experience and wasn’t well versed in the finer points. The editor asked me something like, “Do you see sailing as a competitive thing or a romantic thing?” Without hesitation, I answered, “Definitely a romantic thing.” Whoops.

As I recall, at the time, the magazine was pretty much exclusively about racing. I’d raced a bit, but I preferred tooling along in a summer sou’wester, barefoot and shirtless, sipping a beer and making the boat go as fast I could on whatever point of sail kept me in the sun. Never far from my mind and fancy were all those who came before me in all those beautiful wind-powered machines enduring hardships, pursuing riches and chasing adventure.

I’ve never been one to mix relaxation and competition, save the occasional light wager on the golf course or besting another guy to a random buoy or back to the yacht club bar. I get it though. A few years back, I spent a week at the St. Barth’s Bucket, a superyacht sailing regatta in the Caribbean. I sailed on three distinctly cruisy boats—96-foot (29.2-meter) S&S/Derecktor Altair, 169-foot Dykstra/Royal Huisman Meteor and 184-foot (56-meter) Holland/Perini Navi Zenji. I found their owners, who were, save one, primarily cruisers and pretty much engaged in the racing (two of them had paid professionals flown in for the event), which was kind of cool. While I wasn’t at the wheel, or even pulling strings, my latent competitive side emerged and I found myself tracking the competition in our classes.

For all the fun that was, the best part was scanning the horizon for the big classics and faux classics such as Adela and Elena of London as they wound through their labored tacks looking every bit like yacht racing in the days before modern maxis and hyper-cats capable of highway speeds. To be sure, all the owners were doing their best to win, but the whole thing still had a relaxed vibe. The Bucket’s mantra always has been “Win the Party.” That’s more my game.

Thinking back, as I stood on the docks in Boston in 1976 watching the fleet of tall ships parade down the harbor in the Bicentennial Operation Sail event, I was taken with a sense of nostalgia, squinting to imagine the scene from that wharf a century earlier when sailing ships were still used for commerce. Those ships were always pushing to beat their competition to a shrinking number of cargoes still economical to be shipped under sail—fertilizer, lumber and other low-value bulk materials. It occurs to me now, those guys were always racing and in conditions you could hardly call relaxing.

I still like to get the best out of a boat and beat the boys to the bar, but I’ll take that laid-back, shoeless, shirtless, sun-drenched sailing any day. Probably a good thing I didn’t get that job.