I’ve been fascinated by Ernest Hemingway since the day I discovered him in grade 9 English. The clean, simple prose of The Old Man and the Sea captivated me, as did his life on the Italian Front during the First World War and in Spain during the Spanish Civil War. His tortured relationships with his four wives and other writers added to the psychological complexity of the man who arguably had the greatest influence of any writer on 20th-century American literature.
On and off over the past 27 years I have sought out and visited the bars, homes, hotels and tropical saltwater fishing spots that were so much a part of his life.
Toronto, Canada
Hemingway was first invited to Toronto in 1920 by Chicago businessman Ralph Connable, who oversaw the expansion of Woolworth stores across Canada. Ernest first moved into the Connable home at 153 Lyndhurst Avenue in Toronto’s fashionable Forest Hill and, after being introduced to an editor at the Toronto Star, began writing for them.
Later, Hemingway moved to 592 Sherbourne Street, which is now the Clarion Hotel Selby Downtown. Today, fans of Hemingway can rent his old room, which has retained the architectural features of his era. Hemingway and his first wife, Hadley, also resided in one of the apartments at 1599 Bathurst Street.
Paris, France
In December 1921, Hemingway became a correspondent for the Toronto Star in Paris. There, Ernest and Hadley moved into their first apartment at 74 rue Cardinal Lemoine. Far from luxurious, it had no running water and the toilet consisted of a slop jar in a closet.
Around the corner, a brasserie at Place de Contrescarpe is where the opening paragraph of A Moveable Feast is set. James Joyce, one of Hemingway’s true lifelong friends, lived across the street at 71 rue Cardinal Lemoine. A 20-minute walk away to 27 rue de Fleurus is the former apartment of Hemingway’s literary mentor, Gertrude Stein.
If you’ve ever bought a book at Shakespeare and Company at 37 rue de la Bucherie in Paris, believing it is the store that Sylvia Beach once owned—and where James Joyce had Ulysses published and Hemingway hung out—I have some disappointing news. The new location doesn’t have anything to do with Sylvia who, in fact, closed her store in 1941. The real Shakespeare and Company was first located at 8 rue Dupuytren and later moved to 12 rue de l’Odeon.

La Closerie de Lilas in Paris is where Hemingway and F. Scott Fitzgerald planned their disastrous trip to Lyon, France.
For some serious drinking, Hemingway would frequent Brasserie Lipp at 151 Blvd. St-Germaine, which today still has the feel and look of a 1920s brasserie. Across the road from Brasserie Lipp, at Les Deux Magots, Hemingway and James Joyce would pound a few back. To see where Hemingway and F. Scott Fitzgerald planned their disastrous trip to Lyon, make your way to La Closerie de Lilas at 113 rue Notre Dame-des-Champs.
Key West, Florida, U.S.A.
In 1928, Hemingway and his soon-to-be-wife, Pauline, left Paris and visited Key West, Florida. Hemingway loved the heat and warm ocean breezes, and was soon introduced to deep-sea fishing. In Key West, Papa spent a great deal of time drinking at Sloppy Joe’s—not to be confused with the newly rebuilt Sloppy Joe’s in Havana. As well, the current Sloppy Joe’s in Key West is actually the second bar of the same name. To find the original Key West Sloppy Joe’s, round the corner where you’ll find Capt. Tony’s Saloon.

There are three Hemingway-related Sloppy Joe’s bars, the first two are in Key West, Florida while the third is in Havana, Cuba. Above is the second Sloppy Joe’s which most people are familiar with while the original is around the corner and is now known as Captain Tonys Saloon.”
North Bimini, Bahamas
Between 1935 and 1937, the Compleat Angler Hotel on North Bimini, Bahamas, was where Hemingway spent his time fishing, drinking and machine gunning sharks from a dock. Unfortunately, the hotel burned down in 2006, with the hotel’s owner losing his life after saving a guest.

The Compleat Angler Hotel on North Bimini, Hemingway’s home away from home while in The Bahamas during the 1930s.
Havana, Cuba
Hemingway began living in Cuba at Havana’s Hotel Ambos Mundos in 1932 and lived there off and on until 1939, claiming it was the best place to write. You can visit room 511 where he always stayed. There you’ll see some of his fishing gear, a Remington typewriter, which he apparently used to write For Whom the Bell Tolls, and the bed where he had a steamy love affair with Jane Mason, which lasted for several years while he was married to his second wife, Pauline.

The third corner room from the top is Room 511 at Havana’s Hotel Ambos Mundos which Hemingway rented for a several years before permanently settling in Cuba.
Papa loved his rum and just a short walk from Hotel Ambos Mundos you will find his favourite watering hole, El Floridita. At the end of El Floridita’s bar is a life-sized bronze statue of Hemingway placed at the spot where he would always drink.
A short stagger around the corner from El Floridita is the stunningly beautiful, newly resorted 1926 art deco Bacardi building—the former headquarters for Bacardi Rum. When the Bacardi family fled Cuba after the 1959 revolution, Bacardi was nationalized and has since become Havana Club. It was Bacardi that hosted Papa’s Nobel Prize party. Across the street is a small, dilapidated bar that Hemingway occasionally frequented.
In 1939 Martha Gellhorn, then Hemingway’s love interest and soon-to-be third wife, was tired of living at Hotel Ambos Mundos and found Finca Vigía (meaning “Lookout Farm”), which became Papa’s home until 1960. With original contents, Finca Vigía has been restored to the point of almost looking the same as when Hemingway lived there. To wander around the property and gaze in to rooms filled with his books, clothes, bull fighting posters and taxidermy hunting trophies from his African safaris takes you back to his era.
Cojimar and Cayo Guillermo, Cuba
To the north of Finca is the small fishing village of Cojimar, where Hemingway kept his custom-designed boat, the Pilar, which was captained by Gregorio Fuentes—the model for Santiago in The Old Man and the Sea. Papa and Gregorio would always eat at the same corner table at La Terraza de Cojimar, with its panoramic view of Cojimar bay and the Spanish fortification that guards it. When Hemingway died the local fisherman took up a collection and built a monument to Papa.
If time permits, visit Playa Pilar on Cayo Guillermo. This was Hemingway’s favourite beach and fishing area. The beach is stunning with its gin-clear turquoise and light green waters. There is a small restaurant where you can find shade from the noonday sun, have a beer and take it all in.
Photo Credits
All photos by Diane Frey – All Rights Reserved
First published at Travel and Escape
You missed Istanbul! He lived there too!
Great read, I also love Hemingway stories.
Hi Valerie, I agree that Hemingway wrote great stories. Ken Burns will be releasing a two part documentary on Hemingway during 2019. In my article above I only wrote about the places that I visited up to the date of publication in 2014. Since then I have visited his two home in Oak Park and his townhouse in Chicago, as well as travelling to Spain and visiting Pamplona and his favorite fishing spots on the Irati River in the Navarre Pyrenees and the associated towns of Lekunberri, Auritz/Burguete, Aribe and Yesa. This past February, for the third or fourth time since 1986, I visited his home in Key West. Next year I am thinking of visiting the places that he was stationed in in Italy during the First World War. Cheers, Joseph