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

On a cool spring day with the trade winds whipping whitecaps across the Bahía de Perros, it's obvious what drew Hemingway to the palm-crowned islets of the Jardines. The keys range from the size of a traffic circle to 4,000-acre Cayo Romano, and many are interconnected by shifting shoals and sandbars. They appeared, he writes of the archipelago, as a "line of green keys that showed like black hedges sticking up from the water and then acquired shape and greenness and finally sandy beaches."

The chain officially begins in the province of Matanzas and stretches 289 miles southeast to Camagüey. The area is a waterman's Eden, with more than 1,000 marked dive sites and enough anchorages and beaches to explore for months in a yacht or sea kayak. The nearby coral reef is one of the largest continuous reefs in the world and shelters some 900 species of fish. The waters bordering the Old Bahama Channel are known to offer some of the best deep-sea fishing in Cuba, while the inshore flats harbor mythically large bonefish.

Hemingway had been exploring the Jardines for years, since buying the Pilar in 1934 for $7,455 from Brooklyn's Wheeler Yacht Company. The boat was constructed with an oak frame and equipped with a custom fighting chair, a 75-horsepower Chrysler engine for cruising, and a 40-horsepower Lycoming for trolling. 'For Whom the Bell Tolls,' published in 1940, had made Hemingway into America's most celebrated writer; it was to Cayo Romano, Cayo Guillermo, Cayo Coco, and the islands around Nuevitas where he went to escape his newfound fame. ("Book selling like frozen daiquiris in hell," he wrote to his first wife, Hadley Mowrer, in January 1941.)

Papa researched many of the 'Islands' passages with his lover, Jane Mason, a notoriously wild millionairess. Fishermen say he'd hole up with her in a shack for days, leaving only in the afternoon to hunt birds with a shotgun while Mason collected seashells. Fishing and boating were also a salve for his gnawing depression, and he took to them passionately, losing himself in the Jardines for months at a time, getting to know local fishermen and collecting material for what would become his most famous and most puzzling novels.

From Havana we follow roughly the same course Hemingway did on his voyages to the Jardines, albeit on land in a Czech Skoda station wagon. Instead of navigating reefs and squalls, we dodge livestock, suspicious police, and wizened farmers peddling blocks of salty cheese in the middle of the six-lane A-1 highway. Between comments on my erratic, hungover driving, Antonin tells stories of being taken hostage in Afghanistan and following the U.S. invasion of Iraq via Kuwaiti rental car. He refused to be embedded, and on several occasions came close to getting killed.

As we approach the Jardines, we can see that much has changed since the Pilar sailed here. The most dramatic transformation came when Soviet subsidies dwindled and Castro turned to tourism to fill the void. In 1988, the first of a network of pedraplenes ("roads on the sea") was completed to Coco, and over the next 10 years 3,000 rooms went up on Coco and neighboring Cayo Guillermo. To visualize our base at the Tryp Cayo Coco, one of 11 "all-inclusive" resorts on the two keys, imagine Captain Merrill Stubing T-boning the Love Boat into Gilligan's Island, building wooden staircases to the beach, and hiring a crew of hyperactive dance instructors to yell at guests 14 hours a day through remote headsets. With 502 rooms, six restaurants and bars, a discotheque, gymnasium, amphitheater, tennis courts, free drinks 24 hours a day, and the best Tom Jones impersonator in Latin America, the Tryp stands as a testament to Castro's Vegas envy.

After one dispiriting night there, we escape with a fly rod. Our fishing guide, Orlando Gonzales, meets us outside a neighboring hotel with a neatly packed backpack and a shirt advertising Coco's "Parque Natural," a scruffy brush patch on the island's old airport. Thanks to Castro's intense paranoia, maps in Cuba are almost nonexistent, and asking directions, even from locals, often leads to more questions than answers. (A car rental agent aptly named Morón told us a two-hour drive would take two days.) Lucky for us Gonzales navigates by watching the ocean, and he leads us directly to the yellow-and-black-checkered Diego Velázquez lighthouse by which Hudson and Hemingway navigated the archipelago.

"[Hudson] looked up at the white-painted house and the tall old-fashioned light and then past the high rock to the green mangrove keys and beyond them the low, rocky, barren tip of Cayo Romano," Hemingway writes.

We can see Romano from the lighthouse's parapet, as well as 5,000 square miles of ocean and beach that Cuba's tourism boom hasn't touched. From the tip of Cayo Cruz to Coco and Guillermo, the water between the keys deepens from aquamarine to green-blue to navy. On the horizon, towering thunderheads ink the ocean black beneath them while breakers billow in front of a lone tanker cruising the Old Bahama Channel.