May 2009
By David Roper
Years ago, back in my boat delivery days, I was hired to help a couple head off on the first leg of their dream. They were an anxious pair, long on their romantic vision of “escaping and living the dream,” and short on the practical part: sailing. That didn’t stop them, though.
They were excellent at severing ties: They had sold their house, sold both their cars, quit both their jobs, and even cancelled their marina slip. They had read all the escapist literature, and even poked out on the bay a few times, but never too far from shore. Nervous about the first leg, they had hired me at the last minute.
Forty miles out, on the way to Norfolk, it got rough and unpleasant, the wind brisk and astern. The following seas eyed their odd vessel hungrily. Strange creaks and groans began to emit from both the vessel and its owners. The missus came up to the cockpit, looked around frantically, and shrieked, “Where’s the land? Oh my God. Where the hell is the goddamn land.”
Anyway, what happened next is a long story, but the short version is, I was told to “turn around and take us home.” So we motored upwind into steep seas for 11 hours, back to the marina where we had started. The owner sat next to me in the cockpit, looking aft and downwind at his vanishing dream. He never let go his grip on the big cockpit cleat beside him. He said nothing. He didn’t have to: His white knuckles said it all. In less than one 24-hour day, the dream was over.
Robert Persig, author of the 1974 mega best seller, Zen and the Art of Motorcycle Maintenance, bought an offshore sailboat with some of the profits from his book, and headed for “The Dream.” Years later, he wrote an essay about it saying that all that really happens when one “escapes” the realities of life ashore is simply the substitution of one set of shore-based problems for a new set of ocean-based problems. There is no real escape of problems, pain, pressure, discomfort and worry, only a different set of each, he said.
If you understand that, that’s fine. If you understand that you don’t leave your soul or your past behind when you sail away, that they go everywhere with you, that’s fine. Otherwise, to quote Persig: “All this is just running away from reality. You never realize how good that friendly old nine-to-five job can be. Just little things – like everyone saying hello each morning, or the supervisor stopping by to get your opinion because he really needs it. And seeing old friends and familiar neighbors and streets you’ve lived near all your life. Who wants to escape all that? Perhaps what cruising teaches more than anything else is an appreciation of the real world you might otherwise think of as oppressive.”
In 1980, when I captained a cruise ship on the Mississippi River in St. Paul, I had a friend who owned a barge company. He’d built it up from scratch, into a successful business over many years, but he’d always talked of “getting out of here,” building his dream boat, heading down the Mississippi and then to the Caribbean. Finally, he did it. He sold his company and left. Six weeks later he was back.
“The islands all started looking the same,” he said. “I’d get up, worry about the anchorage, worry about where I would get water, worry about the next front coming through, and then worry about my next destination, which I wasn’t even particularly interested in going to anyway. One island started to look like the last one. I needed some sort of goal. After a while, the goals I did have began to seem empty. I missed my business and all its challenges.” My friend sold his boat, came home and bought back his company.
Tristan Jones, who wrote numerous books of his picaresque life sailing the oceans of the world in low-budget craft, grew weary of his nomadic lifestyle also. Towards the end he discussed his thoughts about “the dream” and “paradise.” Why, he wondered, was turquoise water and an endless white sand beach considered “paradise?” What do you get with paradise, anyway? Challenge? Nourishment? Intrigue? If you anchored off it, or sat on it for, say, several days, wouldn’t “paradise” be eclipsed by boredom? Wouldn’t it then be time to escape paradise?
Well, he’s almost convinced me. But maybe I’ll give it just one try and see for sure. I’ll see you by that fourth sand dune on the left, the one with the palm tree. (Bring the brie; I’ve got the wine.)
Dave Roper sails out of Marblehead, Mass.



We have complete issues archived to 2009. You can read them for free by following this link.