Key West is both an island and a city in the Florida Keys at the southern tip of the longest north/south road in the U.S. The city’s main street is Duval St., 1.1 miles long. Located on it is the famous Sloppy Joe’s Bar. Sloppy Joe’s opened the day after Prohibition was repealed, December 5, 1933. The owner was a good friend of Ernest Hemingway who gave the bar its name . In 1937, it moved across the street to its present location, which was built in 1917. The first photo is dated 1938.
Also on Duval St. is the old armory building, which was built in 1901 and is seen here in a 1902 photo. The building is now an artists’ community.
There are many other attractions too numerous to mention here, but some of the most popular are:
The old Island City National Bank building, which was built in 1901. The Bank opened in 1914 and was the main developer of Duval St. The building is now a restaurant and bar that opened in March 2019. The first photo is undated.
The Custom House. This building opened in 1891 as a custom house, post office, and court house. It sat abandoned for 20 years and then was purchased by the State of Florida in 1991. The state then leased the building to the Key West Art and Historical Society. The first photo is dated 1900.
The southernmost house in the U.S. It was built in 1897 and was the first to have electricity in Key West, thanks to a friend–Thomas Edison. It was a speakeasy in the 30s, a night club in the 40s, and now is a B&B. The first photo is undated.
The Hemingway House. This residence was built in 1851 and was occupied by Ernest Hemingway from 1931-39. It is a landmark and major tourist attraction with six- and seven-toed descendants of Hemingway’s original cats. Oddly, it sits just 16 feet above sea level yet is the second highest point on the island! The first photo is dated 1934 and the last one shows the current owner.
