Ernest Hemingway & The Key West Connection

“It’s the best place I’ve ever been anytime, anywhere, flowers, tamarind trees, guava trees, coconut palms…”

Ernest Hemingway traveled around the world and lived in different parts of the country but for the legendary American author, Key West was in a league of its own. 

The esteemed novelist first learned of the island city from longtime friend John Dos Passos, who told Hemingway and his wife, Pauline Pfeiffer, that they would love it. 

Hemingway’s first foray with Key West came in 1928 when he arrived via ferry from Havana, Cuba. 

According to the Florida Keys News Bureau, the quick stop turned into an extended stay when the car that was supposed to be waiting for them was delayed. 

As compensation for the inconvenience, the dealer offered the Hemingways accommodations at the Trevor and Morris Apartments above the dealership.

With the help of Pauline’s wealthy uncle, the Hemingways moved from their apartment to a large house at 907 Whitehead Street. It was in that Spanish colonial villa, in his second-story writing studio,  that Hemingway began writing “A Farewell to Arms.”

The 1929 novel shares a first-person account of an American soldier falling in love with an English nurse while serving in the ambulance corps of the Italian Army during World War I. 

“After ten years of meditation and digestive of his experience, Hemingway lays before his readers a work which is far from a mere war experience, nor a store of love and death during the war,” biographer Carlos Baker wrote. 

“A Farewell to Arms” became Hemingway’s first best-seller and marked his place as one of the preeminent modern American writers.

Other pieces partially penned in that home included “For Whom the Bell Tolls,” “The Green Hills of Africa,” “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.”

But the one novel that intertwined Hemingway and Key West was “To Have And Have Not.” The 1937 novel was Hemingway’s only story with a Florida backdrop and only his second novel set in the United States.

“To Have And Have Not” tells the story of Harry Morgan, a fishing boat captain from Key West, who under economic strain during the Great Depression turns to running contraband between Florida and Cuba.

The book was released to mixed reviews, and Hemingway himself admitted to it having some weaknesses. Frank L. Ryan, author of “The Immediate Critical Reception of Ernest Hemingway,” explained the criticism as such:

“To Have and Have Not (1937) was not well received. Almost all of the critics thought it signaled a decline. There was scattered applause for some features: the style, dialogue, and some of the narrative action; and concerted cheering for others: the bar-room scene; the main character, Harry Morgan; the bedroom scene involving Harry and his wife. However, the most serious and extensive concern of the critics was with two elements in the novel which were inter-related, the social theme and the structure…. On the whole, the adverse criticism was accurate in pinpointing the faults of the novel: the confusing shifts in point of view, the eagerness to destroy the rich and the powerful, the irrelevant attacks on literature through Richard Gordon, the writer in the novel. The major shortcoming of the criticism was related to the strong emphasis placed on sociological values by critics who seemed to be seeking accurate reflections of contemporary events. This is most clearly shown in the reluctance to view Harry Morgan as a symbolic figure, and the readiness to judge him in terms of his relevance to actual social problems. Delmore Schwartz’ view that Harry’s morality was inadequate because it could not be associated with a domestic situation is a little like rejecting Moby Dick because it is impossible to associate him with deep sea fishing from a rented boat.”  

Despite the negative press, the novel was adapted for the silver screen in 1944, starring Humphrey Bogart and Lauren Bacall. 

But Hemingway wasn’t all books and no play in Key West. If he wasn’t deep-sea fishing, “Papa” Hemingway was drinking with his “Mob” of friends at Sloppy Joe’s Bar. Hemingway became close with Joe Russell, the owner of Sloppy Joe’s, who was the inspiration for the character Freddy in “To Have and Have Not.”

Even though Hemingway left Key West in 1939, he left his mark on the island city. His house as designated a U.S. National Historic Landmark in 1968. Descendants of his six- and seven-toed cats still prowl the property. On a yearly basis, Hemingway look-alikes descend on Key West for the Hemingway Days festivities. 

In other words, Hemingway’s adventurous spirit forever lives on in Key West.