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Walking the Plank: Jonathan Boulware

Capt. Jonathan Boulware started his sailing life in traditional small boats at Mystic Seaport in Connecticut, where his father worked, and was for many years a tall ship skipper. As a captain and educator he has sailed the waters of New England, the North Atlantic, the Caribbean and Southern California. These days, Boulware has the biggest command of his career, at the helm of the South Street Seaport Museum in New York City. As executive director Boulware has returned the museum’s focus to the waterfront, to the ships and piers that built the Big Apple, and to vibrant programming both ashore and afloat. 

Photo by Sam Dole.

“While I’ve had great experiences at sea, and while many of those were life-altering, what I’m doing right now at the Seaport Museum is really a great privilege,” he says. “Best moment? Right now.”

First memory of being on a boat: Family lore has it that I was out sailing at night in Fishers Island Sound when I was 3 days old. My memory of that particular voyage is poor.

First boat you owned or skippered: My first command as a fairly newly licensed captain was the lovely 1928 oyster dredge schooner A.J. Meerwald, sailing with students from Bivalve, New Jersey, and Philadelphia. But I also remember another first. The day I figured out how sailing worked was in the Mystic River in a Pete Culler “Good Little Skiff,” and I was probably 10 or 11. I had sailed downwind and struggled mightily to get back, hitting the bank and shoals and all manner of things along the way. And then it clicked! I found the balance of sheet and tiller and weight, and I was suddenly able to go to weather. It was as exciting as if I’d been flying.

Last or current boat: Sadly, I spend a great deal of my time now sailing a desk. The Seaport Museum has a remarkable fleet, though, and I do get out in the 1885 Pioneer from time to time. Lettie G. Howard is a past command, and she’ll always be one of my greatest loves.

Favorite boat you’ve owned or skippered: I truly don’t have a favorite. I love Lettie for her sweet lines and incredible handiness. I love Tole Mour for her confidence at sea. I just sailed a dinged-up rental Rhodes 19 in Provincetown [Massachusetts] Harbor and had some of the most fun sailing that I’ve had in years.

Your dream boat: I’m a bit focused right now on the efforts at the Seaport Museum, so my thoughts go right to Wavertree. The current $13 million restoration will get Wavertree very, very close to being able to sail in New York Harbor. She’s a mighty three-masted, full-rigged sailing ship, and there may well be an opportunity to sail her. That’s at the top of my list.

Most rewarding professional experience: I’m right in the middle of it! I’m working with a dedicated team of sailors, staff, volunteers and the community to rebuild a very important institution in a very special place in the world. I walk to work. My son is growing up at South Street. And we have a collection of interesting and active vessels run by a really stellar group of people.

Scariest adventure aboard: Probably aloft in an April gale in the North Atlantic with broken gear swinging about. Not sure that it was the scariest at the moment; there was work to do, so we were focused. But in hindsight it was one of the most dangerous.

What you love about sailing: It’s actually not the sailing. Sailing is fine, but it isn’t inherently better than skiing or surfing or hiking or chess. What I love most is the positive impact that voyaging under sail has on individuals and groups of people. The timid must step forward. The bold learn that caution can be a virtue. And invariably all emerge from a passage — the more challenging the better — feeling that something real has been achieved that could not have been done alone.

Favorite destination so far: San Miguel Island in California’s Channel Islands. It’s like someone took a little piece of Ireland and stuck it in Southern California waters. The first time I arrived there it was in dense fog, and I could hear the surf pounding the island before I could see it. We anchored hearing the surf but without seeing land. When it cleared it was the most beautiful, rocky, rugged vista. I still have an abalone shell I picked up while free-diving there.

Favorite nautical book: When I was a kid I read and reread a book called Windsong Summer [by Patricia Cecil Hass]. I was entranced by the idea that a teenage boy could voyage by himself on a small sloop. As an adult, though, I’m a perennial Conrad fan. Youth and Typhoon are my two favorite stories.

Favorite quote about the sea: Back to Conrad here. From Youth: “Between the five of us there was the strong bond of the sea, and also the fellowship of the craft, which no amount of enthusiasm for yachting, cruising and so on can give, since one is only the amusement of life and the other is life itself.”

This article originally appeared in the October 2016 issue.