Returning to Key West from an African safari in 1934, Ernest Hemingway stopped off in New York to take a few meetings. At one with the editor of Esquire, Arnold Gingrich, Hemingway was given a $3300 advance for some short stories. He promptly took himself out to Coney Island to the Wheeler Shipyard and used the cash as down payment on a customized yacht.

Wheeler was known and rewarded for producing exceptional hand-crafted wooden boats. It had begun producing a pleasure yacht called the Playmate in 1920 and been very successful (the model would be produced until 1939.) Hemingway’s modifications to the 38-foot version he ordered included a live fish well and a wooden roller spanning the transom to aid in hauling fish aboard. He also requested extra large fuel tanks (diesel) so he could stay at sea for longer periods of time. The boat had two motors  a 75hp for traveling and a 40hp for trolling. And he requested a flying bridge. The photo on the opening page shows Hemingway atop that flying bridge as thePilar pulls out of Havana harbor.

The finished yacht cost $7500 and was brought to Key West and christened the Pilar. (Not only the name of the heroine in For Whom the Bell Tolls, Pilar is also the nickname for then-wife Pauline.) Through Key West friend and hardware store owner, Charles Thompson, Hemingway gained permission to dock her at the Navy Yard (the Navy was barely using it at the time.) This put the ship at dock only a few blocks from Hemingway’s home on Whitehead Street. The photo at the top of this page is of Hemingway and Carlos Gutierrez on the bridge of the Pilar in Key West, 1934. Photo courtesy of JFK Library.

Hemingway and Martha

Hemingway met Martha Gelhorn, a journalist who became the third Mrs. Hemingway in Key West.

In 1940, when Ernest and Pauline divorced and he subsequently married Martha Gelhorn (whom he’d met at Sloppy Joe’s,) they relocated to Cuba and built Finca Vigia (Lookout Farm)  the home on a hilltop overlooking Havana where they lived for more than 20 years. Pilar was docked at Cojimar.

Hemingway spent his mornings wrestling with his typewriter and his afternoons wrestling with marlins in the Gulf Stream. He downed daiquiris at The Floridita bar, shot pigeons at the Club de Cazadores, and trolled the Caribbean for German submarines (inspiration for 1970’s Islands in the Stream, about an American artist who pursues German U-boats in Cuba). The writer often sailed to Havana to buy international newspapers (material for 1937’s “To Have and Have Not,” about a rum runner shuttling between Cuba and Key West).

Much of Hemingway’s time in Cuba was spent writing thousands of letters, for which he kept a second desk. In 1944, Martha convinced him to leave scribbling behind and join her in covering World War II in Europe. In London, he met Mary Welsh, the petite Minnesota journalist who was to become his fourth and final wife. After Hemingway’s 1946 divorce from Martha, the pair returned to Cuba, exchanged vows, and shared their home with some 57 cats.

In 1951, Hemingway hammered out a story that had occupied him for two decades — the tale of an old Cuban fisherman who spent four days fighting a swordfish only to lose it to sharks. “The Old Man and The Sea,” published in a single issue of Life magazine, won him up to ninety fan letters a day — plus the 1953 Pulitzer Prize and the 1954 Nobel prize for literature.

Hemingway brought all of his famous friends who visited him in Havana to The Floridita, his favorite bar. Here he entertains Spencer Tracy (left) and Mary, his fourth wife (right).


Pilar was an integral part of Hemingway’s life. Above, in 1950, he’s shown in the onboard cabin. When he left Cuba in 1960 with fourth wife, Mary, he knew he’d be back. But the Bay of Pigs invasion in 1961 cut off his return and separated him from his beloved Pilar. After Hemingway’s death in July of that year, his widow gave the ship to Gregorio Fuentes who had served as her captain. Fuentes also served as the basis for the character in The Old Man and The Sea and passed away in 2002 at 104.

The Cuban government is now owner of the Pilar.


Today, Finca Vigia is a museum. Pilar is on display atop the tennis courts with a walkway encircling her so visitors can view the interior. Attempts by Americans to aid in the restorations have been stymied by politics, even though

the home is listed as “endangered” by the U.S. National Trust for Historic Preservation. Hopefully, things will change and soon we can walk through the front door of that other tropical Hemingway home.