The Beachy Florida Watering Hole That Was Once Part Icehouse, Part Morgue

When you think of Key West bars, Jimmy Buffett immediately comes to mind, since the late musician seems to have frequented more bars in this Florida city than George Washington slept in Virginia homes. Needless to say, Capt Tony's Saloon has a Jimmy Buffett connection, since he played there when he was just getting started and was allegedly paid in tequila (a drink he preferred to margaritas).  Buffett later wrote about the bar in a song called "Last Mango in Paris" and even inscribed the lyrics on the wall above its men's room urinal. 

Other celebs known to have frequented Capt Tony's include Tennessee Williams and Truman Capote, while Ernest Hemingway may have knocked back a few martinis there. But even these famous patrons aren't the most interesting thing about the bar; rather, the real story lies in the building's colorful backstory.

428 Greene Street was constructed in 1851 as an icehouse, but in those pre-refrigeration days, it also doubled as the city morgue. It was also built around a tree said to have been the site where 17 people were hanged — one of whom, naturally, is rumored to haunt the bar.

Several decades later, the building was the site of a telegraph station that passed on news about the Spanish-American War. It later housed a cigar factory and a brothel before finally becoming a saloon. While it's gone through several different name changes, it's been Capt Tony's since 1958, when it was purchased by charter boat captain Tony Tarracino.

Capt Tony's Saloon is undoubtedly a tourist destination, and one with an extensive selection of merch, ranging from t-shirts to Tony Tarracino's autobiography. However, the one thing you won't get there is a meal. Though it was the original site of Sloppy Joe's bar, and likely served its namesake sandwich back in Hemingway's time, it's now strictly a bar. It also doesn't seem to be a fancy cocktail kind of place, since the website doesn't feature a bar menu, though it does have a signature beer in Capt Tony's Amber Ale.

Many TripAdvisor viewers are surprised that Capt Tony's doesn't really play up the historical aspect as much as it could. While the website freely discloses the bar's background, patrons who don't do their research ahead of time might have to pull out their phones to look up the meaning of the famous names painted on the bar stools (they're said to be those of the patrons who once occupied them) or why there's a tree covered with bras. (Actually, we don't have an answer for why the hanging tree or the ceiling are adorned with undergarments.) Overall, Capt Tony's draws mixed reviews, with some finding it a decent enough dive bar, while others are unimpressed by the service, high prices, and overall lack of ambiance.