Key West Things to Do Free Strand Key West
The historic Strand is now a Walgreens drugstore

Key West has evolved into a full blown tourist city with 25,000 inhabitants. Winter is the busiest season. The streets, restaurants and bars are full of tourists. Both times we went to Key West was in November. Outside of the Hurricane and the winter season. It was busy but manageable. 

Key West has attracted different groups of people over the years. Pirates, fishermen, ship wreck salvagers, writers, politicians, hippies, spring breakers and the gay and lesbian communities. The activities revolve around the ocean, restaurants and bars. There are lots of tour companies that will take you fishing, scuba diving, snorkelling, or walking around the historical sites. The nightly sunset party at Mallory Park with music and buskers performing is one of the most popular activities in Key West.

Throughout the year there are all kinds of events; Key West Theatre, Waterfront Playhouse, South Florida Symphony, Key West King Fish Mayham, The Conch Republic Independence celebration, Fantasy Fest and many others. Click here for current events. 

Things to do in Key West Trolley on Duval St.
The Conch Train on Duval Street

Duval Street is the main commercial street of Key West. It was named after the first territorial governor of Florida. It stretches a mile from the Atlantic Ocean to the Gulf of Mexico. 

The street is lined with boutique shops, restaurants and bars. There is even a butterfly conservatory. The original Margaritaville is on Duval Street and Jimmy Buffet has been known to drop in and play an impromptu set with the house band. Duval Street is also the home of Sloppy Joe’s Bar. Duval Street balconies
Hard Rock Cafe on Duval Street Truman Avenue Cabins
Colorful Cabins on the 400 block of Truman Street Decks West Trolley
Trolley Tours on Wall Street Duval Street
Duval Street West Statues
Historical Memorial Sculpture Garden on Wall Street West Bust Park
Bust Park at 410 Wall Street House
Key West Custom House at 241 Front Street is now a museum

Shopping in Key West Curio Shop Key West
Window shopping on Duval Street Store
Unique Boutiques line Duval Street

The Key West Butterfly Conservatory Conservatory
Butterfly Conservatory on Duval Street Orchard
Orchard Swallowtail feeding on a beautiful purple Orchard Flower Butterfly in flight
Beautiful butterflies soaring through the air Flowers Key West
Beautiful flowers line the streets

Key West Bars Key West Inside Bar
Inside of bar with Hemingway mural on the back wall Ceiling
A bar ceiling covered with dollar bills Bar in Key West
The smallest bar in Key West Sloppy Joe's Bar Key West
Sloppy Joe's Bar has been serving drinks since the 1930s

Sloppy Joe’s Bar in Key West was owned by Joe Russell who owned a number of illegal speakeasies and was a close friend of Ernest Hemingway. Joe named the bar after Hemingway’s favourite bar in Havana, Cuba. Sloppy Joe’s in Havana was a bar and fish market. When the ice melted it covered the floor in water. The patrons said that the owner José (Joe) Otero ran a ‘sloppy’ bar. Eventually the name Sloppy Joe’s Bar stuck.

Joe and Ernest spent many days fishing together followed by many nights drinking together. The original Sloppy Joe’s bar was located where Captain Tony’s Saloon is today. When the scheduled move happened, the patrons picked up their drinks and walked down the street. They sat down in the new location without interrupting their drinking session. Hemingway Fishing

Ernest Hemingway with his friend ‘Sloppy Joe’ Russell after a day fishing . In 1938 Hemingway caught 7 marlins in one day establishing a world record. Joe's Menu
Live music, drink and food is served 365 days a year Hemingway Wall
My favourite spot against the Hemingway wall Joe's Interior
A great location for people watching Sloppy Joe's Bar Key West
This is strong evidence that serious drinking takes place in Key West

Ernest Hemingway Home Hemingway Home Sign

The Ernest Hemingway Home is located at 907 Whitehead Street across the street of the Key West Lighthouse. Built in 1851 by Asa Tift, a famous marine architect, it was designed in the  French Colonial style of the era. 

It is located across the street from the Key West Lighthouse. Tift built the house on the second highest point of Key West. It was made a National Historic Landmark in 1968. 

Admission includes an informative and at times humorous tour.

Ernest Hemingway was born July 21, 1899 and died July 2, 1961. He won the Nobel Prize for Literature in 1954. Hemingway House

Ernest Hemingway lived in the house at 907 Whitehead Avenue from April 1931 until December 1939. The house was purchased by his second wife Pauline Pfeiffer’s Uncle Gus who purchased it for $8000 and gave it to them as a wedding gift. Hemingway Wall Bedroom
Hemingway's bedroom with a sleeping cat
Hemingway Bathroom
The 2nd floor bathroom
Hemingway Kitchen
The main floor kitchen Pool
The contentious swimming pool

 Pauline had the pool built  while Ernest was in Europe covering the Spanish Civil War. She found out that Ernest was in Spain with Martha Gellman, a young journalist that they met a few months before. Ernest had taken a liking to Martha. Pauline was furious. She decided to build a pool where his boxing ring stood.  

She tore down the boxing ring. She applied for a permit to use dynamite to blow the hole required in the hard coral.  Her application was refused so the hole was entirely excavated by hand. This added greatly to the cost. It cost $20,000 to build in 1938. More than Uncle Gus had paid for the house. Almost three times as much.  But, it was the only pool in the Keys. 

Hemingway was outraged when he came home. He confronted Pauline. When he found out the cost of the pool he yelled that you’re spending all my money so you may as well take my last penny. He reached in his pocket for a penny and threw it into the pool penny

Pauline took the penny and had it inset into the concrete apron. She loved to tell the story and the punchline was, that her rich Uncle Gus, not Hemingway, had paid for the pool. Hemingway Cat
One of the 50 or so cats on the property cat toes
Polydactyl cat with 6 toes

The Hemingway Home has a large population of polydactyl cats. There are 50-60 cats that are descents of Hemingway’s original polydactyl cat, Snowball. Snowball was a gift to Hemingway from a captain that he had got drunk with one night. The cats are all named after celebrities with names like Elizabeth Taylor, Cary Grant, and Marilyn Munroe. Hemingway Office

Ernest Hemingway’s den on the upper floor of the carriage house where he wrote “To Have and Have Not”, “Death in the Afternoon”, and “The Green Hills of Africa”. Hemingway House
View of the den from outside Letter Hemingway Wives

Hemingway with his first two wives; Hadley Richardson and Pauline Pfeiffer. Martha Gellmore

Ernest Hemingway’s third wife Martha Gellhorn. They met in 1936 when she was 27 on a Christmas trip to Key West. PapaHemingway

Accommodations in Key West

Interactive Accommodations Map

Key West Restaurants

Key West Resources