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Surprise, Bamboozle, and Delight

Once upon a time in the sea off Tobago, the racing fleet lay at anchor in the velvet dark of a Caribbean night. Along the shore, the graceful boats of fishermen rested beneath the weight of sleeping pelicans. There was the sound of distant surf and the pulse of Calypso from unseen, maybe imagined, musicians. It was a night like that, soft as a myth upon the mind, romantic as a lone sailor’s fantasy. But before you settle down to an escapist’s tale of misty isles and fragrant winds and dreams of Paradise, realize if you will, the setting for this tale. Trinidad and Tobago. That crazy, unexpected little nation hard off the coast of Venezuela, that easily leads the world in its capacity to surprise, bamboozle and delight.

It was 1982, the night before the start of the Second Annual Tobago Race Week. And while the fleet lay at anchor, its captains and crews were ashore studying a chart of the race course, discussing regatta rules, drinking rum and listening to the two most popular Calypso songs in the island: No Toilets and Capitalism Gone Mad. There were skippers of boats from Grenada and Trinidad and Barbados and places to the north including the United States. I had been assigned to cover the event for a yachting magazine. My first chore was to find a boat to ride. Several of the captains favored to win, offered to take me aboard.

They assumed, because magazine editors usually equate news with winning, that I would surely want to focus my story on their boat. I was approached by the American captain Bill McAteer, skipper of the odds-on favorite, the professional racing machine called Immigrant, winner of several regattas to the north. I was approached by the skipper of the Bellatrix. She and her all-woman crew, pleasantly uniformed in identical flesh-colored bikinis, were among the favorites. But, as my wife, Betty, had been assigned as the events photographer, I doubted she would be pleased to photograph me among the ravishing crew of Bellatrix.

Then came Andrew, Duncan, Jango and Sex, captain and crew of a lovely French Beneteau 38 which they insisted could not possibly win. A quick survey of the crew’s red eyes, their seeming inability to stand upright for any length of time, and the rumor that their boat was weighted down with hundreds of cases of Carib, the fine island beer, confirmed their conviction that they were a favorite to lose. In a word, the crew was loose. How much more fun it would be to focus on this strange bunch than on the buttoned-down dandies destined to win. Sensing, perhaps, that I cared more for having fun than winning, they accepted me in their number.

Captain Andrew Kelshall, was the son of a legendary Trinidadian sailor. He wore a battered old captain’s hat like one Humphrey Bogart would later wear in The African Queen. Duncan Richardson, strategist and sail trimmer, was a pilot and crop-duster by trade who knew the winds by name. And there was Jango, a commercial diver by trade, and Sex, a young man from south Trinidad renowned throughout the island for two things. The other was that he could drink a Carib in 3.9 seconds.

I had my captain and my crew and a fine ship to sail on. As Jango, Sex and I raised our Caribs to toast our fine vessel, I asked them the boat’s name. Neither one could remember. Surprise, Bamboozle and Delight. The first surprise the regatta crews encountered was when they came ashore for the first time. Tobago is an island ringed with beautiful beaches and there was no dock ashore from the anchorage.

And so, a man named Mad Dog Aubrey designed a dock, a dock floating on oil drums. But as he brought passengers ashore in his Boston Whaler, the flaws in Mad Dog’s design became horribly apparent. After his passengers danced along the oil drum pontoons leaping wildly in the surf, they encountered the second, more serious flaw. While most floating docks have one end in the water and one end on land, the difficulty with this design was that both ends were in the sea. The passengers, with awful inevitability, would step off the other end into neck deep water. It was like watching a beachhead going horribly wrong.

Probably the biggest surprise about the Second Annual Tobago Race Week was that it would be held there at all. Nothing in Tobago, with the exception of goat racing, is very fast at all. It is a languid, quiet place. Racing implies speed and no one has been hurrying in Tobago since Robinson Crusoe was supposedly chased by cannibals here many years ago. I have been to the island many times and have only seen two clocks. Perhaps it’s significant that the racing fleet was anchored off Turtle Bay.

In spite of Mad Dog Aubrey’s double-ended dock, and the fact that the officials in Tobago were still getting the hang of organizing international regattas, the first race began on schedule. And my captain and crew performed in a rather unexpected manner. Although each morning the flagons of rum were raised before the anchor was, our powerful French boat sailed beautifully. The captain was relaxed, his orders sung out like melodies. Sex handled his duties with joyous abandon. Jango executed his sail changes, jibs and tacks and jibes with easy, though tipsy, grace. Duncan, who knew the names of the wind, created marvelous strategies. The mighty Immigrant was dismasted in crazy, but moderate winds in the first five minute of the first race. We flew passed the essentially naked women of Bellatrix on all points of sail, and on a beam reach only Guaicaipuro, a trimarand built in St. Vincent could beat us. Although neither captain nor crew had a fire in their belly to win, and the bilges contained maybe a thousand or more pounds of booze, our gallant vessel finished third in the first race and second in the next. What a strange feeling it was as we ghosted in passed the dismasted Immigrant and back to our mooring. “With just one race to go, we just might win it all,” Captain Kelshall said, as we stepped off Mad Dog’s dock into Turtle Bay.

Over the first two races, our boat had made a name for itself. I only wished I knew what that name was. I was too embarrassed to ask the captain outright. But you don’t go down to the sea and sail toward glory in the U.S.S. What’s-Its-Name. I tried to lean over the transom, reading the nameplate upside down, but I nearly fell overboard. Then I thought of the race committee computer. This, too, was futile. The children of the race committee were using it to play Space Invaders.

As we approached the start of the final race, I detected a small difference in the mood of the captain and crew. A certain business-like formality that had not been evident before. The captain still wore his wonderful old hat, but there was a certain abruptness in his movements. Duncan, who knew the names of the winds, seemed tense, less relaxed. Orders from the captain were shouted, not spoken gently as on the first two races. I began to realize what was wrong. It was a kind of curse. Although none of us would admit it, we all wanted desperately to win.

Our start on the last race was not good. As we flew after the others on a windward leg, I realized why the Second Annual Tobago boat race was so delightful; why other regattas to the north seemed trendy and forced by comparison. The answer lay among the soft mountains of Tobago and beyond in Trinidad where Calypso and steel band were born. Regattas like Antigua, fine as they are, impose themselves on an island. They are events essentially foreign to the community, a gathering of strangers who act out an assigned role each year. The power of this place, Trinidad and Tobago, is so overwhelming that it imposes itself on any event that comes its way. This tiny island nation, with a population smaller than the city of Peoria, creates new art forms, cutting-edge technologies., Olympic Champions, poets, Broadway actors, Nobel laureates, circumnavigators and statesmen with astounding regularity. Antigua is a race. Tobago is a profound human experience rich with the spirit of adventure.

But, now, winning the regatta was within our grasp. We were gaining on the leader and nearing the final mark. If we could cut it close on this tack…well, we just might win. But if we cut it too close, hit the mark, we would be penalized and would probably finish far back in the fleet. And then, incredibly, it happened.

“You hit the mark, Andrew.”

“Yes, Duncan, I hit the mark.”

We were devastated. What had begun as a lark had become a near desperation to win. And we all knew, Andrew, Duncan, Jango, Sex and I, that we had bamboozled ourselves.

As we sailed back past the dismasted Immigrant, and the naked crew of the Bellatrix, her captain hailed our boat.

“Maybe next year, L’Antillaise.

L’Antillaise. L’Antillaise. What a beautiful name.

Marshall Riggan has been writing and telling stories for over a half-century, several of which were turned into movies and television documentaries. He has enjoyed going on sailing adventures for over four decades. His books, Sulu Sea and The Last Traveler, can be found at