Florida Keys

Key West used to look like that? See old photos of Duval Street, attractions and bars

A Greyhound bus on the Overseas Highway to Key West.
A Greyhound bus on the Overseas Highway to Key West. Miami Herald File

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Looking back at old Miami

Photos and memories of the way South Florida used to look: its streets, stores, events and people.

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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.

MORE PHOTOS: Downtown Miami used to look like that? See old photos of streets, buildings and cars

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.
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.
Blue Heaven in Key West in 1985. Miami Herald File


Logan’s Lobster House.
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.
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.
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.
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.
Key West’s oldest bar. Miami Herald File
Sloppy Joe’s Bar.
Sloppy Joe’s Bar. Miami Herald File

DUVAL STREET

The Strand on Duval Street.
The Strand on Duval Street.
The Kress building on Duval Street in Key West in 1993.
The Kress building on Duval Street in Key West in 1993. Miami Herald File


Key West’s Duval Street in 1976.
Key West’s Duval Street in 1976.
The San Carlos Institute a Cuban heritage center built in 1924.
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.
A helpful tease on the road to Key West. Miami Herald File


A Key West street sign at a well-known intersection.
A Key West street sign at a well-known intersection. Miami Herald File


A historic library sign.
A historic library sign. Miami Herald File


HOTELS

The La Concha Hotel on Duval Street in Key West in 1978.
The La Concha Hotel on Duval Street in Key West in 1978. Miami Herald File
Casa Marina.
Casa Marina. Miami Herald File

This story was originally published July 7, 2023 at 6:32 AM.

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Jeff Kleinman
Miami Herald
305-376-3561
Consumer Team Editor Jeff Kleinman oversees coverage for health, shopping, real estate, tourism and recalls/scams/fraud.
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Looking back at old Miami

Photos and memories of the way South Florida used to look: its streets, stores, events and people.

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