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

The lighthouse signaled the beginning of Hudson's final pursuit of the Germans. It also marks the end of our bonefishing expedition, when it turns out that we'll have to traipse across sharp coral and hot sand, on foot, under the broiling sun, all in order to catch an inedible fish. Our enthusiasm wilts, and we bid Gonzalez (and our $75) farewell.

We follow Hudson's/Hemingway's trail farther the next day, to the cut between Coco and Guillermo where the Germans supposedly passed. A bridge now spans the gap, and we continue along Guillermo, searching for one of the beaches Hemingway and Jane Mason frequented on their trysts. Instead, we find a Disneyesque gas-powered locomotive, dispatched from one of the resorts, marking the entrance to Playa Pilar. While Antonin browses the last chapter of Islands under a palapa, I explore the rocky point at the northwestern tip of Guillermo.

We've been starving all week, thanks to several poorly thought-out laws Castro imposed to foster tourism. Every piece of food a tourist eats must be inspected by the government, and thus sits in a warehouse, getting stale, for at least a week. Fishermen can only keep the head and tail of any fish they catch; the meat must be turned over to the state immediately. And Cubans are not allowed to eat lobster, to ensure that officials have enough frozen, rubbery tails to serve to tourists. So it is more with a sense of appetite than sport that I notice a school of plump Cuban jacks swimming off Guillermo.

An hour later I'm back, fly rod in hand, clambering 30 feet down a razor-sharp coral cliff to cast for dinner. When a dachshund-size tarpon removes my fly with a flick of its head, I opt to join a Spaniard who has arrived with casting gear and a bucket of Rapala lures.

Over the next two hours, I take part in a Monty Python version of 'The Old Man and the Sea.' It takes Pedro two casts to hook his first 30-pound tarpon, but then the oafish hotel manager almost expires reeling the beast in. Twenty minutes and several thrilling tail-walks later, he finally wrestles the fish to the edge of the cliff, at which point he explains in a frighteningly high-pitched wheeze that it's my job to scale down to the water's edge and gaff the fish one-handed. Soon after, he reels in a second 30-pounder, collapsing dramatically on the ground as I lug it, too, up the cliff. I have a brief respite when he hooks a mere 15-pound barracuda, but I'm soon faced with the most difficult endeavor of the afternoon: hefting the 75-pound catch back to Pedro's Audi, where he hurriedly bids adieu and zips back to his hotel with all the fish in his trunk.

After a week in the surrealistic world that is Castro's Cuba, I am beginning to think that Cayo Contrabandos might not exist. Meanwhile, Antonin has begun explaining to complete strangers the improbable factors that miraculously aligned to make me into an asshole and a shithead simultaneously. Thankfully the manager of the marina signs an inch-thick ream of paperwork and nonchalantly nods his head toward a boat tied to the pier. A second miracle comes when our rakish, mustachioed skipper, Jesus Lucio, tells us he grew up in Punta Alegre and has boated around Cayo Contrabandos most of his life.

Jesus drops both throttles and points the 40-foot Toro due north. We tool past the crowded beaches of Coco, the Parque Natural, and Guillermo and swing west into the deep blue waters off Isla Media Luna, finally taking in the seascape that beguiled both Hemingway and his fictional Hudson. Fifty miles to the southeast is Cayo Confites, where Fuentes babysat Hemingway's children when he wasn't captaining the Pilar; to the northwest is Cayo Frances, where Hudson communicated with a U.S. Navy outpost. Off the port bow, Jesus points out a boiler from a tanker sunk during WWII. Directly astern I see "the bight where [Hudson and his first mate, named Willie] had anchored and the beach and the scrub trees of Cayo Cruz that they both knew so well. . . . ."

After clandestinely trading a half bottle of rum to some fishermen for a hunk of fresh tuna, our best meal of the trip, Jesus points out Contrabandos. The tiny two-acre island hovers over the Caribbean like an emerald stepping stone. Mangroves crowd the western tip and a long coral point juts east toward Coco and Guillermo. I spot several sticks marking the sandbar on which Hudson runs aground in 'Islands'; Jesus avoids Hudson's fate by maneuvering along a deep channel leading to the island. There he rafts up with a fishing boat, the same model used by the "lobster police," in the lee of the key.