Captain Tony's Saloon, Key West

Captain Tony's Saloon is housed in a building that has a history as colorful as the town of Key West itself. First built in 1852, the property once served as a morgue, a wireless telegraph station, and later, as a bordello, and a bar popular with the Navy, known as the First National Bank Saloon. During Prohibition, it housed several speakeasies, the last of which was named The Blind Pig and specialized in gambling, women, and bootleg rum.

The location has a rather macabre story to it. There once was a hanging tree standing in its center that was used for public executions – several men are said to have been hung here for piracy. Supposedly, there are bodies still buried underneath the floor (several gravestones reportedly to be found somewhere near the pool tables area). They say the place is also haunted by the infamous "lady in blue" ghost.

In the 1930s, the joint was renamed Sloppy Joe's and is where Hemingway did most of his drinking, while in Key West. In 1968, Tony Tarracino (called Captain Tony), a local charter boat captain, purchased the property, idled for many years by that time, and named it Captain Tony's Saloon.

Eventually, the place has become a cultural icon in Key West, patronized by many well-known artists, writers, and celebrities. A peculiar feature at the bar is that whenever a celebrity guest visits, a bar stool is added with that patron's name on it. Among those whose names have been inscribed on stools at Captain Tony's over the years are Truman Capote, Jimmy Buffett, Shel Silverstein, John Prine, John F. Kennedy, Harry Truman, Bob Dylan, and, of course, Ernest Hemingway himself.

Known for its quirky decor and unique atmosphere, the bar is filled with memorabilia, including license plates, bras, and countless dollar bills and bras hanging from the ceiling. With so much history, this is definitely a spot worth checking out… if you don't mind drinking while standing on someone's grave, that is.

Tip:
Above the sign outside the building is a large Jewfish that Captain Tony caught and preserved. It is said that if you throw a quarter into its mouth, good luck will follow you until you leave the island.