Before it was a Duval Street institution with a clothing-optional rooftop, this corner building operated as John Brown’s Bar, and it’s where a young, broke Jimmy Buffett showed up for informal gigs with a rotating cast of local musicians in the early 1970s. It’s one of the last genuinely open-air bars left on Duval Street, three distinct floors stacked on top of each other: The Bull downstairs with live music most nights, The Whistle upstairs with a balcony made for people-watching, and the rooftop Garden of Eden for anyone feeling bold. The hand-painted murals inside tell the story of Old Town Key West, and the anything-goes energy hasn’t changed much since Buffett’s era.
Thirsty for more? Dive into the Bum’s full guide to the best beach bars in Florida.
