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In the 1930s, the United States and Cuba were occupied with a common enemy: Cuba’s dictator, Fulgencio Batista. The Batista regime was allied with the United States, and Washington was unhappy with this. A few years after his post-World War 1 Havana exile, Ernest Hemingway was recruited by the US Office of Strategic Services, the predecessor to the CIA. He was sent to Cuba to conduct covert operations.

Ernest Hemingway famously once stated that “a writer must be a hack first, and then a poet” and this quote has been quoted ever since. But did he really mean it? Or, was he just being funny? According to a book that claims to put a “whole new slant” on Hemingway’s infamous quote in the new book “Shadow of the Sun: Ernest Hemingway and the Actual Operation”, this statement is just as apocryphal as people believe.

During WWII, the illustrious author traveled the Caribbean aboard the Pilar in pursuit of U-boats.

The day I arrive at Cayo Guillermo, a little tropical island off Cuba’s northern coast in the Jardines del Rey archipelago, it’s eerily silent. The Covid-19 outbreak has wreaked havoc on the country’s tourism business, with most hotels shuttered and unoccupied. The Grand Muthu, which has 500 rooms but just 26 visitors, is the sole establishment open for business. One of them is me. 

I’ve been to Cuba 25 times, but this is my first time staying in Cayo Guillermo. I don’t have a lot of options. The rest of the country is still closed off during the first phase of its post-Covid reopening. I have an ulterior reason, however, because I have a copy of Ernest Hemingway’s Islands in the Stream stashed in my bag. 

During World War II, “Papa” Hemingway traveled here to look for German U-boats. He maneuvered his yacht, Pilar, around Cuba’s rugged northern cays with the help of a motley crew of fishermen, barflies, and semiretired practitioners of pelota, a Basque court sport. Pilar, ostensibly a fishing schooner, concealed grenades, machine guns, and rocket launchers. Hemingway romanticized the encounter in his posthumously published novel Islands in the Stream. However, like with so many Papa legends, the truth is frequently mixed up with folklore. 

The Time Ernest Hemingway Secretly Worked As a Spy in Cuba On the bridge going to Cayo Guillermo in Cuba, there is a statue of Ernest Hemingway. During WWII, the author patrolled these northern Caribbean waterways in search of German U-boats. Brendan Sainsbury (Brendan Sainsbury)

In Cuba, it’s difficult to avoid Hemingway. From El Floridita, the Havana bar where he allegedly downed 13 double daiquiris in one sitting, to his book-lined former home, Finca Viga, where you can look in through the windows at a 1950s freeze-frame of Papa’s life, the ghost of the country’s second-most revered Ernest—after Ernesto “Che” Guevara—is everywhere.   

Cayo Guillermo is a newest lure on the market. The cay was uninhabited until the early 1990s, but a recent hotel-building frenzy aimed at luring sun-drenched Canadian and European tourists has significantly changed its appearance.  

The five-square-mile cay now supports nine all-inclusive resorts and actively promotes its Hemingway connections, thanks to its saline mangrove wetlands and resident flamingos. A Hemingway shopping center and a wooden Hemingway jetty may be seen among the soft, sandy beaches and limestone headlands. I notice three monuments of the writer gracing the bridge connecting Guillermo and Cayo Coco on the ride from the airport. Later that afternoon, I walk over to Guillermo’s main beach, a blonde gem named Playa Pilar after Papa’s fishing boat-turned-spy-boat.

The beach, which is normally crowded with vacationers, is deserted. I like the solitude as I gaze out to sea, where Hemingway, loaded with wine, bait, and bazookas, traveled clandestinely on the Pilar in search of German submarines nearly 80 years ago.

During World War II, the threat of U-boats was very present in Cuban waterways. The country had declared war on Germany on December 11, 1941, the same day as the United States, and was swiftly dragged into the Battle of the Atlantic, which was then in the midst of a long spike.  

German U-boats were sinking roughly 15 Allied boats each month in Cuban seas by the spring of 1942. Due to a lack of firepower, the US Navy turned to local yachters for help, offering them cash to equip their boats with weapons. It was a chance too good to pass up for Cuba’s most famous resident fisherman.  

The Time Ernest Hemingway Secretly Worked As a Spy in Cuba Off the coast of Cayo Guillermo, now a developed resort, Hemingway outfitted his fishing boat Pilar for wartime service. (Ernest Hemingway Collection/John F. Kennedy Presidential Library and Museum)

Pilar’s transformation into an armed spy ship appealed to Hemingway’s sense of adventure. He considered himself fighting the curse of fascism and contributing effectively to the American war effort after returning to Cuba from reporting on the Spanish Civil War. Pilar would mislead German U-boats into an unguarded approach by appearing as a harmless fishing craft, then unload the heavy ammunition. 

If the mission seemed impossible, it was. Pilar’s prospects against a torpedo-wielding German submarine with an 88mm deck gun were slim to none. Even Hemingway subsequently agreed that the whole operation was “simply so impossible” that no one would believe it had happened, according to historian Nicholas Reynolds in his 2017 book Writer, Sailor, Soldier, Spy.

Despite this, Spruille Braden, the US envoy to Cuba, rubber-stamped the ostensibly fatal expedition, promising the writer ammunition, radio equipment, and secrecy. Braden, who had previously collaborated with Hemingway on the “Crook Factory,” a short-lived Cuban spying escapade, was said to be so impressed with Papa’s patriotism and detective ability that he went beyond regular rules to support him.

Others, such as Hemingway’s wife at the time, Martha Gellhorn, were less certain. After serving in Spain, Gellhorn was a daring war correspondent eager to return to Europe’s fight. Reynolds considered her husband’s overzealous U-boat monitoring as “simply a way for Pilar’s skipper to collect scarce wartime fuel for his boat so that he could fish and drink with his cronies,” according to Reynolds. Hemingway, undeterred, collected his squad and embarked on what he dubbed “Operation Friendless.” 

The Time Ernest Hemingway Secretly Worked As a Spy in Cuba Pilar now lives at Finca Viga, the author’s former Havana residence. (Picture Alliance/Peter Zimmermann via Getty Images) )

I decide to go out on the sea myself to get a sense for Hemingway’s U-boat adventures. I walk out to the beach in front of my hotel and convince a jobless Cuban boat operator to take me fishing. Thirty minutes later, I’m floating half a mile offshore on a small sail-powered catamaran, trying to reel in a recalcitrant barracuda and feeling very Hemingwayesque.

I recollect the dramatic ending of Islands in the Stream as I glance back at pancake-flat Guillermo, which is now lined with hotels. The American protagonist, Thomas Hudson, and his crew apprehend the desperate survivors in a mangrove-choked waterway beyond Cayo Guillermo after days of chasing a wrecked German submarine. A shootout ensues, and Hudson, a typical Hemingway hero, is mortally wounded. 

The truth for Hemingway wasn’t quite as heroic as his fiction. During his so-called war cruises in 1942–43, the author spent the better part of a year on the water but only saw one potential U-boat—from afar. Hemingway pursued the mysterious vessel, hoping to get near enough to fire his bazookas, only for it to speed up and vanish. 

That was the end of it. Hemingway and his crew spent the rest of their long patrols playing cards, lobbing grenades at marking buoys, and becoming more bored—and drunk. 

The battle was going against the Axis by the summer of 1943, and the threat of U-boats was diminishing. Hemingway was summoned to Havana by a coded letter. Operation Friendless had come to an end.

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The Time Ernest Hemingway Secretly Worked As a Spy in Cuba Hemingway poses with his sons and a defeated tuna, having been a more successful fisherman than a naval operative. (Ernest Hemingway Collection/John F. Kennedy Presidential Library and Museum)

Despite a 60-year economic barrier with the United States, Cubans adore the great American poet. Every state-run tourism firm worth its salt offers a classic Hemingway trip, and Havana’s principal port is named after him. 

Meanwhile, biographers disagree over how effective Hemingway’s Cuban war efforts were. Kenneth Lynn, author of a 1995 Hemingway biography, says that the whole endeavor was more of a “lark.” Reynolds writes that he “took the task seriously and put his heart into the project.” At the time, Ambassador Braden was effusive in his praise, believing Papa had made a significant contribution to the war effort. Captain Ramrez Delgado, the only Cuban to sink a German U-boat during WWII, was less enthused, dubbing the writer a “playboy who sought submarines on the spur of the moment.”

Personally, I’ve always liked Hemingway for his razor-sharp prose and engrossing stories, while also appreciating the exaggeration that surrounded his larger-than-life lifestyle. He wasn’t a coward, even if he was a star. The author fought valiantly in World War I, worked behind enemy lines in the Spanish Civil War, and then fearlessly reported from Normandy. 

Hemingway’s Cuban adventures were more of a blip on the radar for me. Naive? Yes. Desperate? Perhaps. Things might have turned out differently if his luck had turned out differently. Hemingway, like that other brave American novelist, Jack London, who had confidently headed off to the Klondike 50 years before, didn’t locate any gold, but he did unearth plenty of raw material for his writings.

To travel to Cuba, US residents must apply for a “general license” in one of the 11 categories mentioned by the US Treasury Department (use the search tool and type “Cuba”). The “support for the Cuban people” category is suitable for independent travelers with no specific ties.


Only private accommodations are now available to US citizens; the closest ones to Cayo Guillermo are in the mainland town of Morón. Gran Muthu is one of the nicest hotels on Cayo Guillermo for non-US nationals. The privately managed Hostal Peregrino and the art deco-themed Casa 1932 are both highly recommended in Havana. 

Several seaside restaurants specialize in fresh fish. Lobster, shrimp, and red snapper are served at Ranchón Flamenco in Cayo Coco.


El Floridita (Obispo No. 557) and La Bodeguita del Medio are two of Havana’s most famous Hemingway-inspired bars (Empedrado No. 207).

Take a day excursion with Havana Super Tour to explore all of Hemingway’s attractions, including his home, Finca Viga.

On Cayo Guillermo, fishing trips can be arranged at any of the cay’s hotels.

This story appeared in the World War II magazine in June 2023. 

In the early 1930s, Ernest Hemingway, a seasoned journalist and fiction writer, was increasingly motivated by events in Europe. He had already returned to the United States in 1928 and published the short story, For Whom The Bell Tolls. The book was the first of several classic works that Hemingway would publish during the 1930s. Hemingway would go on to be known as one of the most influential writers of the 20th century. To this day, Hemingway remains popular with readers and critics alike.. Read more about ernest hemingway death and let us know what you think.

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