Hemingway and The Florida Keyes


Joe DiMaggio lies on Ernest Hemingway’s bed at 3 o’clock in the afternoon. It’s arguably the most delightful spot in the entire house, but he is after all the alpha male of the other 54 cats lazing around the property. His fur is a tortoiseshell-tabby-mix and his most distinguishing feature is his sixth toe. He shares this unique oddity with fifty percent of the other cats, who are all descendants of Snow White, the original cat given to Hemingway’s son in 1935 and named after the famous storybook character.

Like Hemingway I adore cats and books so I’m in virtual heaven as I browse through the house where he lived with second wife Pauline Pfeiffer in Key West. After Ernest returned from his travels to report on the Spanish Civil War, Pauline had changed his favourite fighting spot in the garden into a pool. Pauline reputedly took his last cent and that last cent can be seen set in concrete, beside the swimming pool. It was in his studio, at the side of the house that I divined the man and his artefacts that decorate the walls and shelves. The typewriter, beautiful and tempting for any writer to touch sits near Hemingway’s Safari Hat. His animal trophies hang on the wall next to his fishing rods.

Hemingway was a keen fisherman and only meant to spend a few days on the Florida Keys but luckily his car broke down and the replacement part took three weeks to be found. The draw of this idyllic island nestled between the Gulf of Mexico and Atlantic Ocean meant he ended up staying eight years. While here he wrote many of his great works including To Have and Have Not. One of his favourite haunts was at the Blue Heaven on the corner of Thomas Street, a short stroll away from his home on Whitehead Street.

It’s here that Hemingway refereed many boxing matches but back in his day the Blue Heaven was also a dance hall and bordello. I dropped by for lunch with local Carol Shaughnessy, who came to the keys over thirty years ago for a summer and never went home. We shared some of the famous Key West Lime Pie which comes in two guises, with meringue on top and without. She told me families have been divided over the debate of which is the more delicious. Hemingway’s ghost hovers over us in this hip hub of food and music but the time to really see his doppelganger is when his fans flock to Key West every July for Hemingway Days.


At Sloppy Joes on Duval Street, images of the writer, his fishing rods and references to his time in Key West cover the walls. Hemingway stored many of his original manuscripts at Sloppy Joe’s after leaving Key West, including The Green Hills of Africa and To Have and Have Not, his novel set in Key West.  By day, the original Joe, Josie Russell, was also a charter boat captain and Hemingway’s boat pilot.  Hemingway modelled The Queen Conch on Russell’s own boat. Music rings out through the open windows and doors of this iconic establishment all day and night making it one of the best spots on Duval Street.

Key West has truly come of age celebrating 200 years as an important town and was once the richest in mid 19th century America. The name is taken from the Spanish Cayo Huesa, meaning reef of bones, as this small island one mile long by four miles wide was used by natives as a graveyard.

A highlight for book lovers is The Literary Walking Tour. Key West has drawn writers to visit and stay for decades. The Pulitzer Prizewinner, John Hersey, best known for his war Journalism and his account of the dropping of the atomic bomb called “Hiroshima,” lived in Key West. His collection of short stories, Key West Tales, was published posthumously.  One particular story he wrote while living in Key West, called “God’s Hint,” is about a wrecker who also happens to be a Methodist Minister. In the 1800s, before many lighthouses were erected, Key West was a hub for wrecking (responding to sinking ships and salvaging the spoils from shipwrecks). The first Key West lighthouse was erected in 1825, at that time the coastline was averaging a shipwreck a day.  After a devastating fire, the current Key West lighthouse was erected in 1847 and with the reclamation of land in front it now stands strangely one third of a mile from water.  I was rewarded after the climb of 88 iron steps of the now obsolete lighthouse by the breathtaking views of Key West from the highest point on the island. The house built next to it was used to home the lighthouse keepers families and is full of stories about what life was like during the 19th century in Key West. Purportedly Hemingway used the lighthouse as a marker to find his way home from Sloppy Joes!

One of Key West’s best-known and most prolific authors, Judy Blume and her husband, lawyer and crime writer, George Cooper, own the nonprofit bookstore, Books & Books.  Blume most famously pens young adult literature, including Tales of a Fourth Grade Nothing, and the charming, Are You There God, It’s Me, Margaret. Her books have sold over 85 million copies worldwide and she has written and spoken out for intellectual freedom and against censorship, making her adoption of Key West as home all the more appropriate.

Other thrilling ways to explore Key West include the Conch Train that goes from Mallory Square throughout the day. In the evenings this is the spot to watch the sunset with the locals and join in the festive atmosphere with buskers and musicians. It’s around the corner from El Meson de Pepe which has been in business since 1985 and the best place on the island to taste Caribbean food in an authentic Cuban setting. From Mallory Square the highlight was a wine tasting tour with Danger Charters on a sunset cruise where I was dazzled by spectacular views and tasty cheese canopies washed down with a terrific selection of wines from around the world. www.dangercharters.com

Another important writer who made Key West his home includes Tennessee Williams who bought a gingerbread cottage on Duncan Street, in the Casa Marina neighborhood.  He gathered an assortment of writers in the studio he called “The Mad House”. Many different tales of Williams’s life in Key West are told but it is notable that he wrote the final draft of Streetcar Named Desire while staying at La Concha Hotel in 1947.

Elizabeth Bishop made her way to Key West in the early 1930s, and bought an eyebrow house (with elliptical shaped roof windows) on White Street in 1938.  She was an avid fisherwoman, and was beloved on the island and friendly with many locals, including Tennessee Williams

It wasn’t just writers who flocked to this corner of the United States. President Truman carried out many important decisions for the country while living there. The naval base not far away proved to be an importance stronghold, especially during the Cuban missile crisis. His retreat has been used by many presidents since and is named the Little White House and makes a fascinating visit. On the wall is a photograph taken when he was vice-president with Lauren Bacall on his knee. It was an opportunity to promote the two who at the time of taking were unknowns – but not for long.

I stayed at The Perry hotel, luxuriantly set at the marina on Stock Island in Key West. It’s the perfect base to explore Key West with lovely views over the yachts and boats. Every hour a concierge service takes residents into the heart of Key West and it runs until 10.30 at night. Taxis aren’t too expensive either as the buzz on Duval Street is difficult to leave in the evenings. According to local Carol the ultimate time to see Key West come alive is around Halloween when the entire town dresses up for a week. With balmy climate and a knack of dodging the worst of hurricane season Key West has much to boast about it is comes to the end of its 200 year celebrations – not just for book or cat lovers.



Highlight one

The postcard Inn on Islamorada is a perfect stop off for a night on the way down highway one to Key West. The reception desk is a novel sight made up of several books by authors that have connections to The Florida Keys. The Tiki Bar is home to the famous cocktail Rum Runner. Other great dining options on the hotel site include Caio Hound. A short way along the key I enjoyed a spectacular meal at Chef Michael with incredible seafood such as hogfish and yellow tailed snapper. Robbie’s of Islamorada is the place to go and feed the frantic Tarpon fish before taking a boat out to snorkel and see some of the exotic sealife from barracudas to nurse sharks on some of the best coral reefs in America. www.sundancewatersports.org


Highlight two


This year Hemingway Days happens on July 18th and events include the famed Hemingway Look-Alike Contest and a walking tour covering aspects of the author’s Key West years. The tongue-in-cheek Running of the Bulls, a reading of his little-known poetry and a commemoration of his July 21st birthday culminate at an exuberant street fair and a high-stakes three-day marlin tournament that recalls his passion for Florida Keys angling. https://fla-keys.com/hemingway-days/


First Published Sunday July 15th 2023 in the Sunday Independent


Michelle was a guest of The Florida Keys for more information see www.fla-keys.co.uk


Michelle Travelled Dublin to Miami with Tap Air Portugal www.flytap.com

Fact Box

TAP customers can benefit from great value return fares from Dublin to Miami via the airlines Lisbon hub, starting at €501 in Economy Class and €1645 in Business Class, including all taxes and charges. The Portuguese flag carrier operates 15 weekly services from Ireland to Lisbon, and fly’s eight times per week from Portugal’s capital to Miami. For more details, and to book, visit www.flytapcom.


7-night Florida Keys Road Trip with Platinum Travel


  • Inclusive Car hire for 7 days
  • 2 at Postcard Inn, Islamorada
  • 2 nights at Grassy Flats Resort 7 Beach club, Marathon
  • 3 at the Perry Hotel in Key West
  • All airport taxes
  • 24/7 emergency number throughout your stay


Ground only package: www.platinumtravel.com or call 01-8535000