True Confessions of Professional Captains

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Photo by: David Pollard

Admit it. You’ve watched that gorgeous 125-foot yacht coming alongside the dock, her authoritative thrusters positioning her perfectly between two other gleaming megayachts, and her captain, wearing a starched white shirt adorned with official-looking epaulets, standing at the wing controls, calmly giving orders to his young, attractive female crew. You want his job.

Or perhaps you’ve taken your wife and kids aboard a small tour boat to see your favorite city’s waterfront sights, and instead of paying attention to your tour guide, you’ve watched the captain as he deftly controls gear and throttle, using prop wash to precisely maneuver his vessel. He sounds his boat’s baritone horn as he exits the loading dock and heads out into the busy harbor, while his passengers, thrilled to be out on the water, look at him in awe. You’re thinking, “I can do this when I retire. And I’d look good with a white beard too.”

Maybe you’ve had fantasies about selling your house, buying a bigger boat, getting your captain’s license and convincing your wife that she would love serving dinner and drinks to guests who have chartered your boat for private cruises. You could “work” six months a year; the money from charters would take care of your boat expenses, and you could spend the other six months in the islands drinking cold Kaliks and eating fresh conch. What the hell. Carpe diem.

Well, before you quit your day job, maybe you should know what it’s really like to be a professional captain. Yes, there are reasons to be envious of these jobs, but there are surprises and challenges that no seamanship school or captain’s study program can prepare you for. Here are some tidbits from professional captains — their names and particulars have been changed to protect their identities, but their stories are true.

The Couple
Bob and Sue had had enough of their first careers, and once their children were on their own, they sold their home, bought a 50-foot sailing cat and moved aboard. They planned to run a charter business for half the year and go sailing the other half.

Bob is a talented fix-it kind of guy, which is a good thing, because their cat wasn’t new. It was a boat “with potential.” For the first year, every time I visited their boat, Bob was either hanging upside down in the engine room or hanging right side up from the top of the mast. Each week he’d make a list of what needed to be upgraded or replaced, but the list continued to grow.

While Bob was virtually rebuilding their boat, Sue set up the galley and salon for entertaining. To enhance the marketability of their new charter company, she obtained her state license as a minister so that wedding ceremonies could be performed afloat. She also created a color brochure and pitched all the local hotels, restaurants and marinas for referrals.

Their first charter was a wedding at sea. The wedding couple insisted on being married while sailing directly beneath the Chesapeake Bay Bridge, which on a summer Saturday afternoon can be like driving the New Jersey Turnpike the day before Thanksgiving. As Bob was dodging tankers, sport-fish boats, tugs, barges, racing sailboats and skiffs trolling in the main channel, Sue thought it would be a nice touch if she engaged the wedding party in some pleasant ice-breaking conversation. Approaching the groom’s mother, she asked, “So I bet you’re excited. Tell me how your son and his bride-to-be met.” Flicking a cigarette onto the cockpit sole, Mom replied, “Hell if I know, I just met her.”

Things went downhill from there, at least with this charter. But Bob and Sue’s tenacity paid off, and they eventually developed a nice little business. Sue adds, “Don’t try this if you really need the income to live on. It’s a lot of work, but it can earn just enough to go cruising for a couple of months.”