Visiting Hemingway's Islands in the Stream
Credit: The Ernest Hemingway Photograph Collection / John F. Kennedy Presidential Library

"Thomas Hudson looked at the sky and saw the long white hackles of clouds of the east wind. Then he looked ahead at the point of the main key, at the spot of key and the flats that were beginning to show. There he knew his trouble would start."

– Ernest Hemingway, 'Islands in the Stream'

We need a boat. It seems reasonable that a marina would be a good place to start. There's a dock, a row of four charter fishing vessels, and the ultramarine Caribbean lapping at the pier. Photographer Antonin Kratochvil and I are even holding a reservation slip with our names and today's date on it.

Yet commandeering a ship in the only communist nation in the Western Hemisphere – where on the eve of his 80th birthday, the president is sickly and half his constituents would gladly swim the 90 miles to Key West – is proving troublesome. We've been sitting in our rental car for three hours, very much on land and very hot. As two portly cops circle us in a tiny Russian-made police car, I wonder if our 1,500-mile pilgrimage to find the island where Hemingway ended his last novel has come to an abrupt halt.

"Papa would've found a boat, asshole," Antonin says. His other pet name for me is "shithead," or, in his Czech-accented English, "sheethead." On very special occasions, like when I lure a young female traveler back to our hotel or when I manage to avoid wrecking our rental car in a pothole, he combines the two: "Way to go, asshole-sheethead!"

With four marriages and 30 years of war-zone photography under his belt, Antonin stands as the closest facsimile to Hemingway I've found thus far. Which is to say he knows how to stay alive in a foreign country, is ornery as hell, and makes the perfect partner with whom to search for the elusive Cayo Contrabandos.

The island is one of 2,500 in Cuba's remote Jardines del Rey archipelago, a stunning string of keys off Cuba's northern coast some 300 miles east of Havana; it is also the setting for the closing scene of Hemingway's last novel, 'Islands in the Stream.' The Jardines were Hemingway's favorite getaway during his 30-year love affair with Cuba, and they were also the site of his storied World War II submarine-hunting mission, during which he outfitted his fishing boat with U.S. Navy-issue machine guns, hand grenades, and explosives, and set out to sink a German U-boat.

When he sat down to write 'Islands in the Stream' after the war, Hemingway reimagined the mission through the eyes of his alter ego, the stoic painter-warrior Thomas Hudson, who heroically pursues a crew of shipwrecked German submariners in the Jardines. The book is a wild exaggeration of Hemingway's real-life 1942 operation, in which Papa and his crew passed the time playing poker, drinking rum, and tossing hand grenades at sharks. In the final scene Hudson, who like Hemingway suffered from manic depression and was frustrated at being sidelined in WWII, takes a machine-gun blast to the chest in an ambush off Contrabandos. The scene is masterfully rendered, and it eerily foreshadows Hemingway's own death by shotgun. It also made me wonder if finding the island might shed some light on the mystery and tragedy that enshrouded the end of Hemingway's life.

'Islands' proved to be a monster of a novel that Hemingway never finished. His fourth wife, Mary Welsh, found the manuscript in a bank vault in Havana after Hemingway's suicide in 1961, and she had it published in 1970. In his manic editing of the book before he died, Hemingway had removed two sections unrelated to Hudson's sub hunt. One of those became a slim volume called 'The Old Man and the Sea,' which clinched his Nobel Prize in 1954.

Then he returned to work on 'Islands,' his homage to the palm-fringed fishing paradise where he spent some of his last best years and a perfect blueprint for two closet Hemingway junkies like Antonin and me to bird-dog Papa's last great adventure.

Which we are set to complete, if only we can find a boat, a point Antonin makes roughly every 15 minutes. What I haven't told him is that every person I've interviewed on the trip has suggested that the conveniently named Contrabandos may well be one of the few details in 'Islands' that Hemingway made up.