This Old Town stomping ground is actually the original location of Sloppy Joe's, and where Ernest Hemingway was often seen at a barstool until the late 1930s when he left Key West. For a bit of pirate lore, ask the bartender about the “hanging tree” that’s growing right through the middle of the bar. (Hint: It's where 19 pirates were put to death.) The dingy bar is also where Jimmy Buffet got his start. If you can’t decide what to order, get the Pirate Punch, the bar's signature drink.
Key West offers its fair share of premixed cocktails like the classic rum runner and sweet frozen drinks that keep college kids on spring break coming back for more, but there's so much more to the island's cocktail game. True, it's taken a while for the tropical destination to get with the program, but now there are some incredible bars in Key West worth a walk or a ride on the trolley.
While Old Town and Duval Street have some decent spots for people driving in from the mainland and being shuttled in from cruise ships, savvy cocktail connoisseurs know that even better drinks await on the side streets and inside some of the best restaurants where there’s plenty of rum, tequila, wine and craft beer to go around. So after you’ve had all you can take of Key West's beaches and to-do list head over to one of the bars on our list. It's pretty much always '5 o'clock on island time, and the bartender might just make you a cocktail worth bragging about back on the mainland.
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