Key West used to look like that? See old photos of Duval Street, attractions and bars
Jeff Kleinman
Like most places, Key West has changed through the decades.
Tourism became the economy’s bedrock. Chain stores moved downtown. More people, more cars.
But the Southernmost City is still a small town with a sense of history. You may not recognize some places on Duval Street anymore, but the heart of Key West has remained.
Take a look at what a few Key West spots looked like in past decades through the archives of the Miami Herald:
RESTAURANTS
Shorty’s Diner on Duval Street was a favorite of President Harry Truman, who walked to breakfast when he stayed at the Little White House in Key West. Shorty’s closed in 1989. Miami Herald File
Blue Heaven in Key West in 1985. Miami Herald File
Logan’s Lobster House. Miami Herald File
CONCH TRAIN
Locals ride alongside the Conch Train in 1981. Tour guide drivers roll up and down city streets and point out landmarks to the tourists on board. Miami Herald File
The Conch Train on a Key West street. Miami Herald File
BAR SCENE
Sloppy Joe’s Bar in Key West in the the late 1930s with the original proprietor, Josie ‘Sloppy Joe’ Russell, center. Russell was immortalized by Nobel Prize winning author, Ernest Hemingway, as the protagonist Harry Morgan in the classic “To Have and Have Not. The original Sloppy Joe’s location is now Captain Tony’s Saloon. Miami Herald File
Key West’s oldest bar. Miami Herald File
Sloppy Joe’s Bar. Miami Herald File
DUVAL STREET
The Strand on Duval Street.
The Kress building on Duval Street in Key West in 1993. Miami Herald File
Key West’s Duval Street in 1976.
The San Carlos Institute a Cuban heritage center built in 1924. Miami Herald File
LANDMARK SIGNS
A helpful tease on the road to Key West. Miami Herald File
A Key West street sign at a well-known intersection. Miami Herald File
A historic library sign. Miami Herald File
HOTELS
The La Concha Hotel on Duval Street in Key West in 1978. Miami Herald File
