Key West After Dark 🌴🍹
When the sun goes down, Key West turns the volume up. From legendary Duval Street bars and live music to hidden local hangouts, waterfront cocktails and late-night dancing, there’s always somewhere to keep the night going.
Grab a drink. Find some music.
Make a questionable decision or two.
After all, the best Key West nights usually come with a story. 🦜
Stay Tipsy, my friends.
🌴 What Kind of Night Are You Looking For?
🎸 LIVE MUSIC · 🍺 KEY WEST CLASSICS · 🪩 DANCE & PARTY · 🌈 SHOWS & CABARET · ⛵ WATERFRONT ·
🍹 COCKTAILS & TIKI · 🤪 WEIRD & LOCAL
🎸 Live Music & Key West Classics
Guitars • Cold Beer • Sing-Alongs • Island Legends
These are the places where you can walk in for one drink and somehow still be listening to the band three hours later.
Green Parrot Bar
4.3•Bar•Open
Website•Directions•(305) 294-6133
One of the quintessential Key West music bars. It's just off Duval on Whitehead Street, with a strong live-music identity and a much more old-Key-West feel than a polished nightclub.
Green Parrot official site
Smokin' Tuna
4.6•Restaurant•Closed
Website•Directions•(786) 422-9978
A major Key West live-music stop that recently moved to 313 Duval Street. Expect local musicians, cold drinks and an energetic island atmosphere.
Smokin' Tuna official site
Hog's Breath Saloon
4.0•Pub•Open
Website•Directions•(305) 296-4222
A classic open-air Key West watering hole near the north end of Duval with live entertainment at the heart of the experience.
Hog's Breath official site
Willie T's
4.2•Bar•Open
Website•Directions•(305) 294-7674
Open-air Duval Street bar covered in signed dollar bills, with live music and that unmistakable Key West bar-crawl energy.
Willie T's official sit
Irish Kevin's
4.4•Irish pub•Closed
Website•Directions•(305) 292-1262
Loud, interactive and unapologetically fun. The performers involve the crowd, so this isn't necessarily where you hide quietly in the corner.
Irish Kevin's official site
🦜 TIPSY SAYS: Follow the music. You'll figure out the rest.
🍺 Legendary Key West Watering Holes
History • Characters • Stories • Only-in-Key-West
These aren't simply bars. They're part of the island's furniture.
Sloppy Joe's Bar
4.2•Bar•Open
Website•Directions•(305) 294-5717
The heavyweight of Key West bar history. At Duval and Greene since 1937, with live music every day and dancing every night.
Sloppy Joe's official site
Captain Tony's Saloon
Located in the building that housed the original Sloppy Joe's before it moved to Duval and Greene. Dark, weird, historic and unmistakably Key West.
Captain Tony's official site
The Bull & Whistle Bar / Garden of Eden
Three very different experiences stacked on top of each other: street-level bar, upstairs balcony and the famously anything-goes rooftop Garden of Eden.
Bull & Whistle / Garden of Eden official site
🦜 TIPSY SAYS: Come for a drink. Stay for 100 years of stories.
🪩 Dancing, DJs & Late-Night Trouble
Dance Floors • DJs • Karaoke • 2 A.M. Decisions
Rick's Bar & Durty Harrys
This is essentially a nightlife playground on the 200 block of Duval. Rick's complex has multiple venues, live music, karaoke and an upstairs DJ-driven dance club with one of the largest dance floors in the Keys.
Rick's & Durty Harry's official site
Aqua Nightclub / Aquaplex
Dancing, entertainment and cabaret in the heart of Key West's LGBTQ+ nightlife district.
Aquaplex Key West official site
Bourbon Street Pub
A longstanding Duval Street LGBTQ+ nightlife destination with dancing, entertainment and a party atmosphere.
Bourbon Street Pub official site
🦜 TIPSY SAYS: Hydrate. Tomorrow-you will appreciate the gesture.
🌈 Drag, Cabaret & Only-in-Key-West Nights
Shows • Drag • Cabaret • Fabulousness
Key West's LGBTQ+ and cabaret scene has been part of the island's nightlife identity for decades, particularly around the 700 and 800 blocks of Duval.
801 Bourbon Bar
4.2•Bar•Open
Website•Directions•(305) 923-9296
One of Key West's best-known drag destinations, with the upstairs 801 Cabaret and its long-running 801 Girls performances.
801 Bourbon Bar official site
The Birdcage Cabaret at Aquaplex
A high-energy drag cabaret experience with costumes, choreography and audience interaction.
Aquaplex & Birdcage official site
La Te Da
A Key West institution combining dining, drinks, entertainment, cabaret and the Crystal Room in a more polished Upper Duval setting.
La Te Da official site
Bourbon Street Pub
Another anchor of the Duval LGBTQ+ nightlife scene and an easy addition to an Upper Duval night.
Bourbon Street Pub official site
🦜 TIPSY SAYS: Bring an open mind. Leave boring at home.
⛵ Waterfront & Island Vibes
Boats • Harbor Views • Live Music • Flip-Flops
For the night when you want a drink in your hand but don't necessarily want Duval yelling in your ear.
Schooner Wharf Bar
4.2•Bar & grill•Open
Website•Directions•(305) 292-9520
An open-air Historic Seaport institution with live music and working-harbor atmosphere. It's one of the places that still feels distinctly like old Key West.
Schooner Wharf official site
Sunset Pier
4.4•Seafood restaurant•Closed
Website•Directions•(305) 296-7701
Right on the water at the north end of Duval, next to Mallory Square. Sunset cocktails, live music and harbor views make this a great first stop of the night.
Sunset Pier official site
Conch Republic Seafood Company
A big open-air waterfront spot in the Historic Seaport that's especially easy to combine with a harbor walk and other nearby bars.
Conch Republic Seafood Company official site
Lagerheads Beach Bar & Watersports
4.6•Bar•Open
Website•Directions•(305) 509-7444
A tiny waterfront beach-bar shack at the end of Simonton Street. Much more toes-near-the-sand than nightclub.
Lagerheads official site
🦜 TIPSY SAYS: Start before sunset. Let Key West decide when you're finished.
🍹 Cocktails, Rum & Tiki
Craft Cocktails • Date Night • Rum • Slightly More Civilized
Sometimes Tipsy puts on a collared shirt.
General Horseplay
Website•Directions•(305) 741-7599
A playful craft-cocktail bar on Caroline Street with inventive drinks and a darker, cocktail-lounge feel.
General Horseplay official site
Tiki House
Website•Directions
Right on Duval with tropical décor, rum-forward tiki drinks and live music. Basically on-brand before Tipsy even arrives.
Tiki House official site
The Rum Bar
4.5•Bar•Closed
Website•Directions•(305) 848-6674
A small Upper Duval cocktail bar inside the historic Speakeasy Inn with a deep rum selection and a much quieter atmosphere than Lower Duval.
The Rum Bar official site
The Roost
4.4•Cocktail bar•Closed
Website•Directions•(305) 294-2600
Small, intimate and cocktail-focused, with properly made classics and an atmosphere that feels worlds away from a packed Duval dance floor.
The Roost official site
🦜 TIPSY SAYS: Fancy drinks. Flip-flops still acceptable.
🤪 Weird, Local & Wonderfully Key West
Karaoke • Locals • Divey • Stories You'll Tell Later
And then there are the places that don't fit neatly into a category.
Mary Ellen's Bar & Kitchen
Quirky, irreverent and proudly Key West. Food, drinks, games and offbeat events make it a good antidote to polished tourist bars.
Mary Ellen's official site
Bobby's Monkey Bar
A little more neighborhood watering hole than glossy Duval destination. Karaoke and local-bar energy are a big part of the appeal.
Bobby's Monkey Bar official site
Two Friends Patio Restaurant
An old Key West staple that's particularly well known for its karaoke and lively patio atmosphere.
Two Friends Patio official site
Chart Room Bar
Tiny, historic and tucked inside the Pier House. This is more about old Key West stories and character than flashing lights or DJs.
Pier House / Chart Room official site
🦜 TIPSY SAYS: If you end up singing karaoke with someone named Captain Steve, you're doing Key West correctly.