Capt. Tony's Saloon

There is more to Key West than eating drinking and fishing. The history is fantastic.

Capt. Tony's Saloon at 428 Greene St. has an interesting and checkered past history. It was an ice house, a morgue, the tree inside was originally the Key West Hanging Tree. It was a telegraph station, cigar factory, bordello and then the blind Pig Bar. However, in the early 1930's a local 'Conch' Joe (Josie) Russell moved his speakeasy from Duval St. to 428 Greene St. because it was larger and called it "Sloppy Joe's". This is said to be the oldest licensed bar in the state and certainly in Key West. Sloppy Joe's at that time had roulette, craps, blackjack, slots, faro and cello gambling. The back room was called the silver slipper and was the dance hall. (1&2)

This original Sloppy Joe's is where Ernest Hemingway would frequent around 3:30 in the afternoon to socialize. During this period, he wrote several books from 1933 through 1938 when he left Key West for Havana. In prior years, Hemingway would fish out of Key west and down to Cuba. On one of these trips he met Carlos Gutierrez, who was the matrix for his character 'Santiago' in the book 'The Old Man and The Sea'.

Capt. Tony bought the original Sloppy Joe's building in 1958 where it still operates today as Capt. tony's Saloon. Today's Sloppy Joe's bar on the corneer of Greene Street and Duval Street keeps the namesake for the original with all the allure and fun of the past and today. Where the music is loud and the food and drink plentiful. There is much more history to gleen by googling Capt. Tony's Saloon and you can go to: (2) www.seefloridaonline.com/keywestoldest/bar.html and (1) http://www.capttonyssaloon.com/ where much of this information came from and is suggested reading as it is much more inclusive and informative.