The Best Bars in Key West

Key West doesn’t just have a bar scene. It has a bar culture — one that’s been built over centuries, perfected by pirates, fishermen, and more than a few literary legends. Whether you’re crawling Duval at midnight, sipping a frozen cocktail poolside, or catching live jazz in a candlelit lounge, drinking in the Conch Republic is practically an art form.

We’ve done the legwork (and the legwork after that) so you don’t have to. Here are the best bars in Key West, organized by vibe — so you can find exactly what you’re looking for at any hour of the day.

The Best Poolside Bar Experience in Key West

Blue Flamingo Resort — Rum Row & Toasted Coconut Gateway to Key West

If you’re looking for the best poolside bar scene in Key West, Blue Flamingo Resort is the answer — and it’s not particularly close. Home to two distinct tiki bars, Rum Row and Toasted Coconut, plus The Backyard Pool & Social Club, this is where sun-soaked days turn into spirited nights without anyone having to move very far.

Rum Row is the main event: a full poolside tiki bar and food truck serving frozen cocktails, cold local beers, and island-inspired bites — think conch fritters, Key Lime Chicken Club sandwiches, and Fruiti di Key West pizzas. There’s weekly live music, poolside DJs, and lawn games (cornhole, Jenga, shuffleboard, mini golf, ping pong) spread across a sun-drenched backyard. If you want to take it up another notch, reserve the Karaoke Cabana — your own private stage, poolside, for as long as you need it. Check out all the happenings on the website. Don’t forget to book your day pass if you want a chair by one of the resort’s two sprawling pools.

Toasted Coconut handles the more relaxed side of things — a laid-back pool bar perfect for everything from a morning mimosa to an afternoon frozen drink while you debate whether to leave the resort at all.

The vibe: Tropical playground. Tiki drinks. All-day energy.

Best for: Daytime drinking, groups, resort guests and day-pass visitors alike

Don’t miss: Happy hour specials at Rum Row, and the live music lineup — check the schedule before you go.

The Duval Street Classics

Iconic. A little chaotic. Absolutely mandatory.

No trip to Key West is complete without time on Duval Street. Here are the institutions worth your time.

Sloppy Joe’s (201 Duval St) is the most famous bar in Key West — full stop. Hemingway drank here. Live music plays every single night. It’s loud, it’s fun, and yes, it’s touristy — but there’s a reason it’s been packing people in since 1933. Order a beer, soak in the history, and stay longer than you planned.

Hog’s Breath Saloon (400 Front St) lives by its motto — “Hog’s Breath is better than no breath at all” — and it delivers. Outdoor patio, live music, cold drinks, and a crowd that’s always genuinely happy to be there.

The Bull & Whistle (224 Duval St) is three bars in one: a ground-floor pub, a second-floor open-air bar, and the rooftop Garden of Eden — Key West’s only clothing-optional bar. Even if that’s not your scene, the views from the top are worth the climb.

Insider Tip: Hit Duval right after the Mallory Square sunset celebration. The energy is electric and everyone’s already in a great mood.

Dive Bars & Local Legends

Where the regulars are.

The Green Parrot (601 Whitehead St) has been open since 1890 and runs on exactly one principle: good music, cold drinks, no nonsense. Live blues, jazz, bluegrass, and rock — consistently excellent. Sawdust on the floor, vintage signs on the walls, and not a cocktail menu in sight. Perfect. Check their website for the live music schedule before you go.

Captain Tony’s Saloon (428 Greene St) is the original Sloppy Joe’s — the bar Hemingway actually called home before it moved down the street. Dark, historic, a little gritty, and covered in business cards and bras stapled to the ceiling. A true Key West original.

Two Friends Patio Restaurant & Bar (512 Front St) flies under the radar but earns its spot with live karaoke that draws huge crowds, a relaxed patio atmosphere, and a loyal local following.

Waterfront Bars

Best consumed with a view.

Schooner Wharf Bar (202 William St) sits right on the Historic Seaport with fishing boats and tall ships as your backdrop. Open-air, casual, and home to some of the best live music in the city — plus strong drinks and a crowd that ranges from sunburned tourists to salty locals. A must.

Alonzo’s Oyster Bar (700 Front St) trades nightlife energy for something more refined — fresh oysters, cold drinks, and a front-row seat to the harbor at dusk. Perfect for an early evening drink.

Sunset Tip: Get to Schooner Wharf early with a rum punch and watch the light hit the water from the seaport. It doesn’t get better.

Live Music & Late Nights

For when the evening is just getting started.

Rick’s Bar / Durty Harry’s (202 Duval St) is a multi-venue complex with six bars under one roof, live bands every night, and an outdoor stage that keeps rolling until the early hours. Find your vibe and plant yourself there.

Cowboy Bill’s Honky Tonk (610 Duval St) is exactly what it sounds like: line dancing, live country, cold beers, and a crowd that’s genuinely there to have a great time. Unexpected in Key West and absolutely beloved for it.

Virgilio’s (524 Duval St) is the antidote to everything loud — a cozy, candlelit jazz lounge tucked behind La Trattoria with craft cocktails, smooth live music, and an atmosphere that’s a world apart from the street outside. The perfect gear-shift stop on a long night.

Craft Cocktails & Chill Vibes

For the slow sippers.

The Porch (429 Caroline St) is a craft beer and cocktail bar with a wraparound porch, a carefully curated drink menu, and zero desire to compete with the louder bars down the street. Relaxed, excellent, and exactly what night two calls for.

Rum Barrel (528 Front St) takes Key West’s deep rum heritage seriously — impressive Caribbean rum selection, creative cocktails, and bar staff who actually know their stuff. Great happy hour.