Bars & Nightlife
Dive bars, Duval crawl classics, historic saloons, and waterfront hangs. Key West's nightlife is unlike anywhere else on earth.
Live Music / Waterfront / Classics
19 listedSloppy Joe's Bar
Old Town
Hemingway's favorite bar — Key West's most famous watering hole.
Captain Tony's Saloon
Old Town
The original Sloppy Joe's, dripping with history.
Irish Kevin's
Old Town
Raucous Duval bar with nonstop crowd-participation music.
Bull & Whistle
Old Town
Three-story bar with a rooftop deck overlooking Duval.
Fat Tuesday
Old Town
Famous for giant frozen daiquiris to go on Duval.
Rick's Bar & Durty Harry's
Old Town
Multi-level Duval entertainment complex with multiple bars.
Fogarty's
Old Town
Outdoor Duval bar with live music and a patio vibe.
Hog's Breath Saloon
Old Town
Hog's Breath is better than no breath — Key West landmark.
Willie T's
Old Town
Beloved Duval institution with nonstop live music.
Green Parrot Bar
Old Town
Key West's best live music bar — locals-only territory.
Schooner Wharf Bar
Historic Seaport
Waterfront tiki bar with live music at the Historic Seaport.
Garden of Eden
Old Town
Clothing-optional rooftop bar atop the Bull & Whistle.
Margaritaville Key West
Old Town
Jimmy Buffett's original Margaritaville on Duval.
Grand Vin Wine Bar
Old Town
Wine bar and cocktail lounge with live jazz.
Surly Siren Saloon
Old Town
Lively 2nd-floor bar on Front Street with live music.
Celtic Conch Public House
Old Town
Irish pub with live music, food, and happy hour on Front St.
Island Dogs Bar
Old Town
Lively Front Street hangout with live bands and American eats.
Afterdeck Bar at Louie's
Old Town
Oceanfront deck bar at Louie's Backyard with Atlantic views.
Boat House Bar & Grill
Historic Seaport
Sailing-themed dockside bar and grill with happy hour prices.
Dive Bars & Breweries
6 listedOld Town Tavern & Beer Garden
Old Town
Laid-back beer garden with cold drafts and a local crowd.
Pickles Pub Key West
Old Town
Sports bar with live entertainment, food, and drinks on Greene St.
The Alamo Key West
Old Town
Casual grill and bar with food, drinks, and live music atmosphere.
The Dive Bar Shirt Club
Old Town
Small Old Town dive bar with outdoor seating, live music, and a taco menu popular with locals.
The Waterfront Brewery
Historic Seaport
Key West's top craft brewery with marina views.
Cayo Hueso Brewing
Stock Island
Small-batch craft brewery on Stock Island.
Cocktail & Craft Bars
5 listedVirgilio's
Old Town
Underground cocktail bar and club hidden behind La Trattoria.
General Horseplay
Old Town
Inventive cocktail bar with a dice-roll pricing gimmick and serious drinks.
Tiki House Key West
Old Town
The most committed tiki experience in the Keys.
Mary Ellen's Bar & Kitchen
Old Town
Neighborhood cocktail bar and kitchen with one of Old Town's best happy hours.
Bearded Lady Key West
Old Town
Relaxed bar known for its beer, wine, and friendly staff.
LGBTQ+
4 listedAqua Bar & Nightclub
Old Town
Key West's premier drag and dance nightclub.
801 Bourbon Bar
Old Town
LGBTQ+ flagship bar with drag shows on Duval.
Bourbon Street Pub
Old Town
Party bar with outdoor pool and late-night dancing.
La Te Da Cabaret & Bar
Old Town
Premier LGBTQ+ venue with terrace bar, piano bar, and nightly cabaret.