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


Pig Roast

Living aboard a boat gives you an entirely different perspective on the Islands.  Your whole world is water and if you love to swim and skin dive and scuba dive and just feel the wind on your face, sailing is the only thing, really, to do down here.

Probably the best sailing in the world is down here.  Sailors from all over the world come here to sail in the Caribbean, because it’s to sailing what—say—Garmish, Innsbruck, is to skiing.  Once you’ve sailed in the Caribbean—you’ve sailed!  The land is so interesting and the winds are great—steady trade winds blow all over these islands.

I am standing right now, standing in the sand in the darkness on the island of Dominica, deep in the heart of the Caribbean Islands down in the West Indies.  And they’re having a pig roast and I’ve just come ashore from a beautiful sailing yacht, the Sealestial.

In all my travels, having been many times to the Caribbean, I must say that this trip is very different from any I’ve ever taken, primarily because it’s on board a sailing ship.  This gives a flavor and a beat and a tenor to your life all day long down here that makes the entire trip a total experience apart from an episodic experience.

seaboat with name

These vessels are captained usually by intrepid Englishmen—almost all the charter captains are Englishmen who have gone tropic.  And they’re all licensed, master seamen and they sail these sailing vessels in and out of these islands like they’ve been here all their lives.  A different breed.  All through these islands you see people who are expatriates of all nationalities—British, Swedes, Russians, even an occasional American, and they’re all drifting in and out of these islands instead of melding into the background and into the scenery.  It’s that kind of a backwash of civilizations here.  There’s a kind of universal, unspoken, unheralded union around the world of people who are drawn inevitably to the tropics.  The absolute lure that the tropics have for some people is unmistakable.  And when you see it in action, you know that there’s never any come-back.  It reminds me a lot of Conrad’s stuff or some of the stuff that Somerset Maugham did.  You see many guys who in other years would be called “remittance men.”

We’re at a pig roast and any minute now the party is going to break out.  The music has been hot, the night is tropical and cool, the wind is blowing through the palm trees above me.  Truly an idyllic experience.  The band is now resting on its haunches, the rum punch is flowing freely, and it won’t be long before the first course of the first pig announces that it’s ready.  In the meantime, hang loose and watch out for that Caribbean rum punch that sneaks up on you like a godad about to spring out of the dark.

seal boat color frontjacket

So ends Jean Shepherd’s narrative of life during a yachting trip aboard the seagoing Sealestial–the final known radio description of his travel adventures. Although he visits several islands on this trip, it is the voyage on the boat that, for him, is the major adventure– literally, the traveling is the destination.

Stay tuned for a return to Maine and then

some final summing up comments

by Shep and others regarding

the importance of travel.



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