Home » Transportation » JEAN SHEPHERD–Travel– The Windward Islands Part 1 of 2

JEAN SHEPHERD–Travel– The Windward Islands Part 1 of 2



sea boat map

The last known adventure Shepherd makes to far-off places is his 1975 trip to a group of small Caribbean islands from Martinique down to Trinidad, including among others, Barbados, Tobago and Grenada, all known as the Windward Islands.  Only a bit more than a year before the end of his nightly broadcasting, he speaks of the trip on several radio shows, focusing in good part on the actual voyage there aboard one of three sailing ships, each more than sixty feet long, with beams about sixteen feet.  Unusual for him, the main adventure is not the destination, but the pleasure of getting there—on a relatively small ship, powered by the wind and auxiliary engines.  In a way, this journey is the destination.  He may have thought that this might be his final travel tale. (In early 1977, when he left radio in New York, he and Leigh Brown married and moved to Florida, where they lived for the rest of their lives.)

He speaks of mankind’s need to go from place to place and he mentions some of the great explorers who traveled to far-off lands.  With implied rationale for his own inclinations, he speaks of what he considers the inherent nature of man to be nomadic—and maybe even, take off for a tropical isle forever.

His reference to American history’s tradition of people leaving relative safety to perform the scary feat of crossing the seas to brave an unknown land, weds him to an important tradition of the land and people he loves.  The subject neatly caps off his two-decades of quests to encounter the unknown—his constant urge for expanded intellectual as well as emotional fulfillment through new adventures.


Last week I spent a fantastic time.  The whole object of my trip was to retrace a portion of one of Columbus’ voyages.  For those of you who are just tuning in on us and don’t know what this is all about, I’ve been privileged—I’ve been invited by a group of yachtsmen who decided this year to retrace the route that was taken throughout the Caribbean Islands by Christopher Columbus when he discovered the Americas.  Retracing his journey throughout the Caribbean—we’ve been to several islands that he landed on.  I’ve read letters and notes and so on about the various islands.  For those of you who have never spent any time on a sailing vessel, you just don’t know what you’re missing.

seaboat full image

The Sealestial

Oh, what a great sound! [Shep plays a bit of audio of rushing ocean water he recorded] That’s the sound of the turbulent seas hurling past the hull of the Sealestial in a force-5 wind, the sun standing high overhead, the time, one-fifteen P. M., or, if you prefer, thirteen-fifteen.  The flying fish appearing before the bow, en route to the island of Guadalupe.

I think people basically, all of us—I don’t care who you are—man is a nomadic creature.  Not all animals are.  In fact, not many are.  They’re very rare.  Most creatures remain pretty well anchored to their specific range and they don’t move out of it.  You don’t see polar bears hitchhiking along Route 95 down through the Everglades.  Who is it who does that?  You guessed it, right?  It is not the dromedary.  One rarely sees an elephant trying to make his way up to the arctic wastes—just because they’re there.  No.  Who is it who does that?  Man.

Mankind, humankind—they are that.  Now you can say to yourself that you are not, and you wouldn’t be kidding yourself, but everybody has an itch down inside of himself to move over the globe.  Only man is attempting to land probes on Venus, to step on the surface of the moon.  There’s never been a recorded squirrel who looked up at the sky and said, “One day, squirrel-dom will land on Mars.”  It’s man.

Through much of human history, going all the way back to the very earliest days that we know of, prehistory days, much of man’s history is the history of his travels.  The Great Age of Exploration.  Remember when you read that in school?  In fact they named that The Age of Exploration, when people like Francis Drake and Hendrick Hudson, John Cook—now there’s a great man.  These were people who did what all of mankind secretly always wanted to do.  See what’s on the other side of the next hill.

seaboat drawing0007

And there’s no people—no people in the history of man, outside of possibly the Bedouins—that have been more driven by this curious urge—than Americans.  Maybe, perhaps, it’s because of our antecedents.  You know we’re coming into the big year of the bicentennial, and not much has been said about what makes Americans different from the rest of the world.  For one thing, in the very beginnings of America the continent was settled by people who took a fantastic chance.  Imagine what it would be like to leave everything, even if it’s bad.  To leave everything—your entire heritage, you physical homes, whatever security you had through having people, friends, relatives—and just head out into the roaring unknown.

I don’t mean just pull up stakes and move to Australia, which you may just think to do today.  That’s not the same as pulling up stakes and heading out across an incredibly dangerous sea in an inadequate vessel and fantastic hardships into the unknown.  Literally the unknown.  And that’s what our country was started with—with people like that.  Even people who came later were pulling up stakes, giving up everything, and coming to another country—in which they didn’t know where they would land or what they would do.

They didn’t know whether it would work out.  A lot of them stayed where they were.  What was the difference?  No moral judgment, they just were different kinds of people.  This is one of the reasons why the car is more important to Americans than it is to other people in the Western World.  Because we still remain basically a nomadic people.  We want to keep on the move.  People think in terms of when they retire—do they leave their hometown and go somewhere else?  It’s Americans who do that.  So, we’re different, and why do we do this?  For one thing, a lot of people that, when their job is over—now they can do what they’ve always secretly wanted to do.  Move endlessly over the landscape.  How many times have you heard people say, “Well, what I want to do when I retire is get myself one of those Winnebagos and I just want to travel all the time.”

seal boat color frontjacket

Sources of some material:

I discovered on the Internet that author and political observer William F. Buckley, Jr, was an avid sailor, taking a number of yachting voyages with friends and writing about the experiences. For the last of his three books on his boating trips, Racing Through Paradise (Random House, 1987), his boat of choice was “Sealestial” the same yacht that Shepherd had sailed on in late 1975. Taken from that book, images of Sealestial are by Christopher Little, the map by David Lindroth, and the descriptive paragraphs that follows are by Buckley:

I have found Sealestial the (almost–she is not air-conditioned) perfect cruising boat. And here is what you get when you charter a boat like Sealestial:

First, the tangibles. There is a crew of four. A skipper, a first mate, a stewardess, and  cook. There are three cabins. In descending order of luxury, the owner’s cabin, which includes a dressing table, a huge stuffed chair for reading and working, a private bath including shower; a smaller but commodious cabin with hanging lockers and two bunks, sharing a shower and separate toilet with the third cabin, slightly smaller but entirely comfortable….

The main saloon, as boat people call what at home would be called the living room, is square and would hold, comfortably seated, sixteen people….

Stay tuned for Part 2


Happy 100th, Ol’ Blue Eyes


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