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

Tracking Hemingway in Cuba is like probing Graceland for signs of Elvis. In any building that stands the slightest chance of hosting a tourist, his image is more ubiquitous than Fidel Castro's. We spent our first three nights at one of Havana's most prominent Hemingway shrines, the flamingo-pink Ambos Mundos Hotel, in which he penned 'For Whom the Bell Tolls' during the 1930s. Papa paid $2 for room 511 on his first night in Cuba in 1928 and kept the room for more than a decade, until he bought Finca Vigía (Lookout Farm), outside Havana, in 1939.

I took in the hotel's photographic ode to Papa our first night as Antonin gleefully pulled on a Cohiba Robusto in the open-air lobby. The collage documented Hemingway's time in Havana in reverent detail: Papa in front of his boat, the Pilar, with one of 52 marlin he caught in the summer of 1933; at the gold-friezed Floridita restaurant where he entertained Errol Flynn, Gary Cooper, and Spencer Tracy; with the captain of the Pilar, Gregorio Fuentes, on whom he based the protagonist in 'The Old Man and the Sea.' (Fuentes died in 2002 at age 104.)

All Hemingway trails eventually lead to a bar, so on our second afternoon we sidled up to one of Papa's favorites, the seedy Dos Hermanos on Avenida del Puerto. The Spanish poet García Lorca and Al Capone also favored the mahogany-trellised joint. As the sun dropped behind the colonial mansions of Old Havana in a heavy yellow mist and musicians walked in off the street to join the band, an aging barkeep served us cool mojitos with fresh mint and bitters.

The Dos Hermanos and the Floridita, the bar Hemingway made famous by downing 12 daiquiris, its flagship creation, in one sitting, served as the unofficial headquarters for the sub-hunting mission. During just the first half of 1942, German U-boats sank 397 Allied freighters in the Atlantic and the Caribbean, causing George C. Marshall to proclaim the entire war effort to be in jeopardy. Beginning in June 1942, the U.S. Navy mustered some 2,000 private yachts to "passively" patrol the East Coast and Gulf of Mexico, from Maine down to Texas.

Hemingway had already been heading an antifascist spy ring at the behest of American ambassador Spruille Braden. Now Papa volunteered the Pilar for sub-chasing duty and took the civilian patrols a step further by convincing the Office of Naval Intelligence to outfit the fishing boat with Thompson machine guns, hand grenades, a radio, a bazooka, and all the government gasoline she could take.

The general scheme of "Operation Friendless," named for one of Hemingway's cats, was to lure a U-boat alongside with the promise of fresh food and water. When the crew emerged, the sub hunters would open fire and throw explosives-packed fire extinguishers down the U-boat's hatch. The Pilar would then radio Guantanamo Bay and a navy frigate would fish the survivors from the sea, elicit communication codes from them, and wipe out the German undersea fleet. Simple.

The weathered teak decks of the 38-foot Pilar didn't appear up to the task when I inspected them the following day at the Finca. The boat now sits on the tennis court of the Hemingway estate, which has been preserved as a national museum. Through a stand of palms I watched Antonin snoop around the pool in which Ava Gardner reportedly swam naked. On top of the hill sat Papa's colonial home, the southwest corner holding the room in which he typed Islands and scripted articles for 'Colliers' for $1.25 a word. As I inspected the rickety wet bar Hemingway had rigged on the Pilar's flying bridge, the idea of broadsiding what was then the world's most advanced fighting machine with a wooden fishing boat seemed absurd, if not insane.

Hemingway knew this on some level, so he assembled a nervy crew to man the Pilar's first three-month patrol. The core came from his "Crook Factory" of spies – "a bizarre combination of Spaniards: some bar tenders; a few wharf rats; some down-at-heel pelota players and former bullfighters," by Braden's account. In addition, the roster included businessman Winston "Wolfie" Guest, Fuentes, two Basque jai alai players nicknamed "Paxtchi" and "Sinsky" (to throw the grenades), and a marine communications expert named Don Saxon. When Papa's children visited, they joined in as well.

Hemingway carefully maintained the Pilar's cover as a research vessel (which he used in 'Islands' as well), writing to his son Patrick, "All the scientific projects are in fine shape and everything will be okay with them." The scientific research made it imperative to keep fishing lines in the water at all times. So on November 20, 1942, as a slightly batty Hemingway motored the Pilar past the embattlements guarding Havana Harbor, the world's greatest and most heavily armed fishing trip was about to begin.