Top Duval Street Bars
Sloppy Joe's is the iconic one — been on Duval since 1934, Hemingway drank here, live music most nights. It's touristy but it earns its reputation. The Roxy is the better live music bar on Duval. Captain Tony's on Greene Street (original Hemingway bar) is smaller, more character-driven, and less crowded. Skip the standing-room-only bars between Whitehead and Angela — overpriced and watered-down drinks.
Top Local Bars
The Garden of Eden — rooftop section, clothing-optional top deck, distinctly Key West vibe. The Green Parrot on South Street is the locals' live music bar — almost always has music, never a tourist crowd. The Big Rubber on the edge of the tourist zone has cheap drinks and a crowd that's there for the right reasons.
Best Rooftop Bars
The Garden of Eden is the original rooftop. The Westin's harbor bar is more polished with waterfront views — better for a sunset drink. For the best setting of any bar in Key West: Latitudes at Sunset Key — requires a water taxi but has open-water views and a proper cocktail program.
Best Local Dive Bars
The bars on Stock Island near the fishing fleet are the real thing — cheap beer, fisherman clientele, zero pretense. Bamboo near Bahama Village is a low-key local spot. The further you walk from the tourist core, the more locals you find.
Best Live Music Bars
The Green Parrot leads here — local acts most nights, no cover, serious music crowd. The Roxy on Duval has bigger touring acts. For jazz: La Te Da's piano bar has been the best live jazz in Key West for decades.
Browse Key West Bar Crawl Tours on Viator →
Browse Key West Nightlife Tours on GetYourGuide →