Bars & Nightlife

Hemingway's favorite bar — Key West's most famous watering hole.

The original Sloppy Joe's, dripping with history.

Raucous Duval bar with nonstop crowd-participation music.

Three-story bar with a rooftop deck overlooking Duval.

Famous for giant frozen daiquiris to go on Duval.

Multi-level Duval entertainment complex with multiple bars.

Outdoor Duval bar with live music and a patio vibe.

Hog's Breath is better than no breath — Key West landmark.

Beloved Duval institution with nonstop live music.

Key West's best live music bar — locals-only territory.

Waterfront tiki bar with live music at the Historic Seaport.

Clothing-optional rooftop bar atop the Bull & Whistle.

Jimmy Buffett's original Margaritaville on Duval.

Wine bar and cocktail lounge with live jazz.

Lively 2nd-floor bar on Front Street with live music.

Irish pub with live music, food, and happy hour on Front St.

Lively Front Street hangout with live bands and American eats.

Oceanfront deck bar at Louie's Backyard with Atlantic views.

Sailing-themed dockside bar and grill with happy hour prices.

Laid-back beer garden with cold drafts and a local crowd.

Sports bar with live entertainment, food, and drinks on Greene St.

Casual grill and bar with food, drinks, and live music atmosphere.

Small Old Town dive bar with outdoor seating, live music, and a taco menu popular with locals.

Key West's top craft brewery with marina views.

Small-batch craft brewery on Stock Island.

Underground cocktail bar and club hidden behind La Trattoria.

Inventive cocktail bar with a dice-roll pricing gimmick and serious drinks.

The most committed tiki experience in the Keys.

Neighborhood cocktail bar and kitchen with one of Old Town's best happy hours.

Relaxed bar known for its beer, wine, and friendly staff.

Key West's premier drag and dance nightclub.

LGBTQ+ flagship bar with drag shows on Duval.

Party bar with outdoor pool and late-night dancing.

Premier LGBTQ+ venue with terrace bar, piano bar, and nightly cabaret.