The Best Bars in Key West

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.

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.

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.