Two Cuban boats are seen off the coast of Cuba in the Straits of Florida on May 31. (Noah Friedman-Rudovsky/For The Washington Post)

IN THE STRAITS OF FLORIDA —The waters off the coast of Havana were remarkably deserted for a city of 2.2 million. A lone fisherman was bobbing on a piece of foam. Two more waved from a battered skiff.

The ocean floor drops off less than a mile out, and the water turned an electric shade of blue. This is where Ernest Hemingway came to hunt his “monsters.”

“I can’t wait to get out of here,” said Kurt Winters, pointing his boat at Key West, Fla., 97 miles north. During nine days in Cuba, his crew caught only one marlin. He pushed the throttle.

Aboard the boat were five crew members and seven passengers, among them two Hemingways, John and Patrick, grandsons of Ernest.

Winters’s gleaming 50-foot Hatteras sport fishing model, Therapy 2, had come to Cuba for the 65th annual Ernest Hemingway International Billfishing Tournament, May 25 to 30. It was one of eight U.S.-flagged boats to make the trip, navigating an ocean of bureaucracy to get there.

Their visit seemed like one more sign of a new era in U.S.-Cuba relations, or maybe a return to an older one, at least for the deep channel of water between the two countries, the Straits of Florida. Hemingway likened its powerful Gulf Stream current to a river in the ocean. It is still a restless, wild place.

The straits were a symbol of U.S.-Cuba intimacy back then, easily crisscrossed by weekend boaters and car ferries. After Fidel Castro’s 1959 revolution, the busy river became a separation barrier, a 90-mile moat, then a watery graveyard for Cubans desperate to cross it.

Those rafters are some of the few Cubans who have glimpsed their capital from this vantage: the hazy outline of the old Spanish fortifications at the mouth of Havana Bay, the domed Capitolio, the 1950s-era mafia hotels of the Vedado district, and farther west, the blockish Russian Embassy tower, once teeming with Soviet agents.

Now the Obama administration is moving to restore relations with Cuba after 54 years. It has authorized passenger ferries to run again whenever the Castro government is ready to receive them. American pleasure boats like Therapy 2 may soon be making this trip more and more. This is the view of Havana they will see.

Winters barreled in the opposite direction, rolling with the swell and racing toward the 12-mile boundary where it would exit Cuban waters.

Immigration agents and inspectors in Havana had squeezed Winters and his crew for several hundred dollars in bribes, he said, shaking them down as they arrived and again when they left. Some of the U.S. boat captains had to pay even more. Winters was disgusted. “Cuba was on my bucket list,” he said. “I’m never going back.”


Patrick Hemingway, a grandson of Ernest Hemingway, puffs on a Cuban cigar en route from Havana to Key West. (Noah Friedman-Rudovsky/For The Washington Post)

Two people aboard the U.S. sport fishing boat Therapy 2 watch Cuba fade into the distance on their way to Key West. (Noah Friedman-Rudovsky/For The Washington Post)

The Therapy 2 and other U.S. boats had moored at the communist government’s Hemingway Marina, in a city whose state-run tourism industry offers Hemingway mojitos, Hemingway daiquiris and visits to the Hemingway estate, Finca Vigía, where the legendary American lived most of his last 20 years.

Cuba’s Hemingway industrial complex “is sort of overkill,” said Patrick Hemingway, but he has always felt like an honored guest during the eight visits he’s made to the island since 2005. The 49-year-old said he detected a palpable excitement this time, his first trip since the announcement in December that the two countries would restore relations.

“My Cuban friends seem happier,” he said. “They want change, and there is really a feeling that things are possible.”

It was the first crossing to Key West for Patrick and John, too, the trip their grandfather made many times in his beloved, black-hulled “fishing machine,” Pilar.

There is a famous picture of the grizzled, white-bearded American in May 1960 in Havana, shaking hands with a beaming, black-bearded Fidel Castro, age 33. That was the 10th annual Hemingway fishing tournament, and Castro, naturally, had won the contest, hooking the biggest fish. It was the only time the two men met. Hemingway killed himself in Idaho a year later.

He left Pilar to his trusted Cuban fishing companion, Gregorio Fuentes, and the boat is now dry-docked at Finca Vigía, on display for visitors.


Hemingway and Cuba’s Fidel Castro after Castro won the individual championship in the annual Hemingway Anglers Tournament on May 15, 1960. (AP)

Hemingway in 1956 with a 14-foot black marlin weighing more than a thousand pounds, which he caught during a month-long fishing trip in Peru. (AP)

Despite his rupture with the United States, Castro had told Hemingway that he was welcome to continue living in Cuba. Hemingway had donated the gold medal from his 1954 Nobel Prize in literature to the Cuban people.

John Hemingway, 54, author of “Strange Tribe,” a memoir about his family and its troubled personalities, said of his grandfather, “I don’t think he could have stayed.”

“He wouldn’t have liked the control,” he said. “That’s why he liked the sea. It doesn’t belong to any country. You get out here, and you’re totally free.”

His grandfather made this same crossing from Havana to Key West on a ferry in 1928. It was Hemingway’s first time in the two places that would be home for most of his adult life. Hemingway bought the 38-foot Pilar from a Brooklyn shipyard in 1934 with an advance from Esquire magazine, according to “Hemingway’s Boat,” the definitive history of Pilar.


The straits, and the fishing, lured Hemingway farther south, and he moved to Cuba six years later. For the next two decades he wrote, drank, entertained — and seduced — aboard the boat. During World War II, he outfitted Pilar with grenades and a machine gun to hunt German
U-boats when he wasn’t hunting marlin.

Patrick and John’s late father, Gregory, the third of Hemingway’s sons, spent summers in Cuba, fishing on the boat. Gregory would struggle with mental illness, addiction and gender identity issues much of his life, dying in a Miami police holding cell in 2001.

Neither of the grandsons is a dedicated deep-sea fisherman, but they said they were happy to lend the family name to the cause of greater U.S.-Cuba cooperation, especially for the sake of marine conservation and research in the straits, a highway for global commerce and aquatic life alike.

“Cuba’s north coast is a spawning ground for the tarpon, turtles and billfish that go to South Florida, but there’s still so much we don’t know,” said Jeffrey Boutwell, who organized the trip to promote scientific cooperation between the two countries.

What is known is that the great beasts Hemingway landed — monster blue marlins as heavy as 1,000 pounds — have mostly disappeared. The U.S. boat that won this year’s Hemingway tournament caught 11. Other U.S. captains like Winters found the Cuban waters thin.

About 30 miles out of Havana, the city’s skyline dropped below the horizon. Here the Gulf Stream runs fast, pulling warmer water from the Gulf of Mexico into the open Atlantic. Freighters and oil tankers chugged southward, and a pair of cruise ships passed by.


Images of Ernest Hemingway are still popular in Cuba, like this mural at the marina in Cojimar. The seaside village was a favorite of Hemingway's and was the inspiration for the fishing village in “The Old Man and the Sea.” (Noah Friedman-Rudovsky/For The Washington Post)

There were only two Cuban fishing boats in the Hemingway tournament this year. The government tightly restricts Cubans’ access to the sea, hyper-vigilant for unauthorized departures. Washington’s so-called “wet-foot/dry-foot” policy means any Cuban who reaches U.S. soil can stay, while those intercepted en route are sent back. Havana says the policy encourages risky, illegal crossings.

But Cubans on rafts and small boats know that if they catch the Gulf Stream in the right place it’ll carry them up toward the Keys. Or push them into the open ocean. It is impossible to make the crossing and not think about how terrifying it would be to traverse the straits this way.

Winters bought his $1.5 million boat from a Cuban American businessman who had made the journey as a rafter two decades earlier. His wife didn’t survive. He had named the boat Miss Rosie in her memory, Winters said.

Again the waters changed 30 miles from Key West, the shallower depths turning the surface a pale, iridescent green. American fishing boats began to appear, then sailboats, Jet Skis and windsurfers. The marinas of Key West came into view, crowded with million-dollar yachts and vacationers. Winters’s crew bellowed a rendition of “God Bless America.”

The other side. Another world.

“Brother,” Hemingway wrote in “To Have and Have Not,” “don’t let anybody tell you there isn’t plenty of water between Havana and Key West.” Certainly there was even more than that now.

But the straits had shifted before. They were the subject of what is believed to be the author’s longest-ever published sentence, 424 loosely punctuated, cascading words, too many to reprint in full.

“ . . . this Gulf Stream you are living with, knowing, learning about, and loving, has moved, as it moves, since before man and that it has gone by the shoreline of that long, beautiful unhappy island since before Columbus sighted it,” Hemingway wrote in “The Green Hills of Africa,” published in 1935, referring to Cuba.

“ . . . that stream will flow, as it has flowed, after the Indians, after the Spaniards, after the British, after the Americans and after all the Cubans and all the systems of governments, the richness, the poverty, the martyrdom, the sacrifice and the venality and cruelty are all gone . . . ”