Key West is a tiny island located at the very end of the chain of Florida Keys. You can casually stroll from the Atlantic Ocean on the island’s south shore (at the southernmost point in the U.S.) to the Gulf of Mexico on its northern shore (at Sunset Pier) in about 20 minutes. That is, if you can resist stopping off for a cold one at Sloppy Joe’s, one of the bar shrines to Ernest Hemingway, along the way. So it makes sense that you can also tipple at two of the smallest bars in the world here. The Smallest Bar in Key West, on Duval Street, is a 72-square-foot establishment – “about the size of a jail cell” according to the bar’s website, with two barstools at a bar about the size of child’s school desk. The place is a fun, quick-stop bucket list item and if you manage to find it and make your way inside through the sidewalk throngs, it’s worth ordering a shot and taking a photo.
The second smallest bar on the island is The Orchid Bar, a cabana-like refuge on the grounds of the Orchid Key Inn off Duval Street. The place is a poolside convenience for hotel guests and a tiny treasure sometimes discovered by curious passersby. Unlike the usual Duval Street parrot head saloons, here the atmosphere is cool and refreshing with a smooth white marble bar and shimmery tiles that reflect the filtered sunlight off the pool outside. With only six barstools, and standing room for about six more, the setting is intimate. Often, people in the bar are already friends or family on vacation saying at the inn, but newcomers are quickly made to feel a welcomed part of any happy group inside. Classic and new wave cocktails are expertly mixed and served by affable bartenders. Small but high-tone wine list.
Even better, there’s not a TV in sight. Instead, a beautiful orchid arrangement usually brightens the room.
1004 Duval Street, Key West, FL 33040