The Best Bars in Key West

Pull up a stool at a rum bar, enjoy a glass of wine outdoors on a porch, or cool off waterside with a craft beer – there’s no shortage of options when thirst hits in this part of the Florida Keys.

429 Caroline St, Key West, FL 33040, USA
The Porch shares its porch with another bar, Caroline’s Other Side, but you won’t likely confuse the two. While the Other Side is all about the cocktail, the Porch sticks to beer and wine, and that tight focus pays off. With an international selection of brews on regular rotation, and a casual and friendly vibe, the bar has become a favorite of locals and a few savvy tourists since it opened. At any given time, the chalkboard over the bar lists 18 draft beers on tap as well as 50 more available in bottles. Tropical plants set the relaxed mood on the shady front porch, and the interior is decorated with eclectic art and photography.
429 Caroline Street
In the land of piña coladas and light beers, The Other Side cocktail lounge is chiseling out new booze territory one ice globe at a time. Drinks, loosely inspired by the Keys, are like nothing else on the island. There’s the frothy Ramon Fizz, a mix of gin, lime, cream, egg whites, and fleur d’orange, or twists like the fennel martini, and for purists, a serious list of bourbon, whiskeys, and 16 rums. The small space feels a world away from the beach, with touches of old-school Hollywood glamour: a marble-topped bar, padded white leather bar stools, and a painting of a peacock tail fanned across one wall. When you need a break from the sun and throngs, this is the place to tuck in with a good book, or a good date (snag the chess board if you’re feeling ambitious).
601 Whitehead St, Key West, FL 33040, USA
Chances are that when you return home after your trip to Key West, someone will ask you if you went to the Green Parrot. It’s that kind of iconic bar, the kind your parents’ friends ended up at over spring break in college long ago. The bar started as a local grocery store about a hundred years ago; the building became the Brown Derby, a bar that was popular first with the submarine sailors from the naval base down the street. When the naval base closed in the ‘70s, the bar transitioned into a hangout for fishermen and local sailors and the hippies that began to drift into town. The Green Parrot still has the air of a honky-tonk, lit exclusively by spotlight and neon, with a roster of almost-nightly live music, mostly of the bluesy, rollicking sort.
420 Appelrouth Ln, Key West, FL 33040, USA
Mary Ellen’s is known for its delicious grilled cheese sandwiches, which are made in nine gooey varieties and are accompanied to the table by a wide selection of dipping sauces. The menu makes a half-hearted (a little joke there) effort to promote healthy options like kale salad and avocado toast, but really it’s all about the bar food at this friendly neighborhood joint in Old Town. The game’s always on the television, and there’s a regular schedule of trivia contests, open-mic comedy nights, and beer-fueled spelling bees, all of which go well with grilled cheese.
6810 Front St, Stock Island, FL 33040, USA
Hogfish Bar and Grill, under a thatched palapa roof with open sides, is tucked in among the boats and gulls of Safe Harbour Marina in Stock Island. In short, a meal or a drink there makes you feel like an insider, a salty local far from the crowds downtown. That in-crowd feeling is burnished on weekends, when local bands play sets, or during one of the events held by Hogfish during the season, like shrimp boils. The simple food is served generously on plates crowded with side dishes. The hogfish sandwich, served fried on Cuban bread, is the stuff of late-night-post-beer legend.

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