Key West is a party town.
And Duval St. is the heart of the action.
Fourteen blocks, Gulf to Atlantic, about a mile and a quarter long. A street the state's tourism people call, with a perfectly straight face, the longest street in the world.
It isn't…but you'll swear it is by the 700 block.
Pull up today's happy hours, see who's playing tonight and keep the dive bars handy, because a crawl goes better with a plan you're going to ignore.
0 Duval
You start with the Gulf at your back at Sunset Pier, at the Ocean Key Resort, a dockside bar with live music and the water right there, the kind of view that makes people propose on very short notice.
Have one. Watch the boats. You've got thirteen and a half blocks to go.
1 Duval
Across the way, at the Pier House, is the Chart Room, an old-school bar where the hot dogs, popcorn and peanuts are free, and that's not a gimmick, that's foundation work for the night ahead.
This is one of the ‘old school’ Key West bars. It has quite the history, especially with the Conch Republic.
Our friends at Island Audio Tours of Key West have put together an amazing self-guided audio tour that will turn you into a local in no time.
115 Duval
You pass Bagatelle, in an 1884 house with wraparound balconies, and you look up and somebody is already up there with a mojito watching you, because on Duval people-watching runs in both directions. It’s true!
201 Duval
The corner of Duval and Greene, and the big one, Sloppy Joe's, which by its own history opened on December 5, 1933, the day Prohibition ended, run by Joe Russell, who'd been selling drinks the illegal way before that and who was Hemingway's fishing companion and boat pilot.
It didn't start here, it started around the corner at 428 Greene. In 1937 the landlord raised the rent from three dollars a week to four, so Russell picked up the whole bar and moved it here, which is the most Key West thing that has ever happened to a lease.
If you're here in July, during Hemingway Days, the room fills with white-bearded men competing in the Hemingway Look-Alike Contest, each one sure he's the one, in the full heat of a Key West summer.
428 Greene, a short detour
Turn the corner and walk to the old address, which is now Captain Tony's Saloon, in a building the bar's own history says went up in 1851 as an ice house that doubled as the town morgue.
Tony Tarracino bought it in 1958 and later became mayor of Key West, from 1989 to 1991, and you'll find a hanging tree growing right up through the room, the bar says, with a legend you should let the bartender tell you, under a ceiling covered in bras and posts papered in business cards.
The 200 block
Back on Duval, the bars come so close together here it starts to feel like Golden Gai in Tokyo, a couple of hundred tiny bars packed into a handful of alleys, except with more sunburn and fewer whisky snobs.
- Tiki House, at 203, has a secret back bar that used to be a bank vault, finally storing something people line up for.
- Rick's and Durty Harry's are a whole complex, eight venues by their own count, with what they call arguably the biggest dance floor in the Florida Keys
- Irish Kevin's opened in July 1998 and has live entertainment seven days a week, and its slogan, roughly, is that you came, you drank and you won't remember, which is less a slogan than a weather forecast.
- Hog's Breath Saloon is just around the corner on Front Street, in Key West since 1988, insisting all these years that a hog's breath is better than no breath at all.
224 Duval
The corner of Caroline, and three bars stacked on top of each other like a wedding cake, the Bull & Whistle.
Go up to the middle layer, The Whistle, a second-floor bar with pool tables and a balcony that's the best seat on the street for watching the craziness below.
The roof is the Garden of Eden, clothing optional, no cameras or phones, the tourism council and the bar's own page confirm all of it, and you are on your own from here.
The 300 block
Fat Tuesday is pouring frozen daiquiris in colors not found in nature, and The Grand sits in a Victorian mansion with an almost secret bar in the back, perfect for a twenty-minute escape when you need one.
Just off the street here, Bali Bar is a tiki bar with a pool and live music where, we hear, many a late-night swim has happened, no names.
500 Duval
Margaritaville, which needs no explanation if you were around in 1977 and only a short one if you weren't.
Keep going to Willie T's at 525, where the walls are covered in dollar bills, left by people who decided that was the best use of a dollar, and you know what, maybe it was.
The 700 to 900 blocks
The street changes up here and gets more fabulous, home to some of the island's best-known LGBTQ bars and cabaret stages, and everybody's welcome.
At 801 Duval, 801 Bourbon says the World Famous 801 Girls perform nightly, and a block back the Bourbon St. Pub is the bar that lowers a giant red shoe, with a performer riding it, at midnight on New Year's Eve.
Docs on Duval, at 708, does barbecue in the building that used to be Pinchers, and up at 917 Martin's has great bartenders and a happy-hour deal worth timing your walk around.
Around here you remember you have a stomach, and Sushi Song, at 925, is one of the few kitchens that keeps going very late into the morning.
1125 Duval
La Te Da, built in 1892 by a cigar manufacturer named Teodoro Perez, and in May of that year José Martí stood on the balcony and gave speeches about Cuban independence, and the name comes from La Terraza de Martí, the place says.
Tonight that same building has the Piano Bar at La Te Da inside, and a piano under a revolutionary's balcony is a fine second act for any building.
1400 Duval
The street runs out of road and there's the Atlantic, and Seaside Cafe is right there, a walk-up spot with ocean views and a sky bar, so sit down, you've earned it.
The Southernmost Point buoy is down this end too right now, a stand-in the City put at the south end of Duval while the seawall gets repaired, so your crawl ends at a landmark that isn't quite where it's supposed to be, and neither, at this point, are you.
Greene Street, 4 AM
Not done? Walk back to Greene Street and Tattoos & Scars, a roadhouse-style bar with a great pool table, which stays open until 4 AM no matter what.
Tomorrow, do it smarter, start with today's happy hours, see who's playing tonight, pick from all the bars and dive bars, and keep late-night food in your back pocket.
And in late October this whole route becomes a parade, which is a different animal, and how Fantasy Fest got that way is a whole other story.
Sources
- Visit Florida: Duval Street
- American Planning Association: Duval Street, a Great Street (2012)
- City of Key West Code of Ordinances, Sec. 18-87 (open containers)
- Sloppy Joe's: History
- Keys Weekly: Sloppy Joe's celebrates 85 years
- WGCU: Hemingway hopefuls return to Key West (2026)
- Captain Tony's Saloon: History
- Captain Tony's Saloon: Capt. Tony
- Rick's Key West
- Irish Kevin's
- Key West Express: Irish Kevin's
- Hog's Breath Saloon: History
- The Bull & Whistle
- Florida Keys & Key West: Garden of Eden
- The Bull: Garden of Eden
- Florida Keys & Key West: Fat Tuesday
- Florida Keys & Key West: Willie T's
- 801 Bourbon Bar
- Keys Weekly: Red Shoe Drop tops New Year's Eve in Key West (2026)
- La Te Da: History
- City of Key West: Southernmost Point (temporary buoy)
