From Sloppy Joe’s And Captain Tony’s To The Green Parrot, Discover The Key West Bar Scene
Key West nightlife isn’t about velvet ropes and flashy nightclubs. It’s about legendary watering holes, live music drifting onto Duval Street, colorful bartenders and locals who know where to find the best party. From Sloppy Joe’s and Captain Tony’s to the Green Parrot and Schooner Wharf, here’s my firsthand guide to the bars, music and laid-back nightlife of the Conch Republic.
Editor’s Note: This article was updated in 2026
By Kevin Wilkerson, Editor & Publisher PubClub.com
I went down to Captain Tony’s to get out from the heat…
This line from a Jimmy Buffett song pretty much describes the bar scene in Key West. People walking down Duval Street on a warm afternoon give up the notion of doing anything productive and stop into one of the many decades-old bars made famous by Hemingway, Buffett or those famous only to the locals.
This starts the Key West PubClubbing adventure.
There is only one mega dance club on the island yet the music is everywhere. Even the smallest of bars have live bands.
The music plays from noon until closing. It doesn’t take long to see the same artist pop up later in the day at another club with different band members. It’s the unofficial Key West Musical Tour and it keeps the musicians employed enough to enable them to keep living here.
Legendary Key West Bars, Pubs & Watering Holes
The center of Key West’s socializing is located within a two-block area of Duval Street near Mallory Square. Tourists – particularly those just here for a weekend – do not stray far from this area. Locals tend find their thrills at a few pubs away from this busy area.
The king of Key West bars is Sloppy Joe’s. If it doesn’t become a personal landmark upon arrival, it will be soon enough. Sloppy Joe’s was a fishing buddy of Ernest Hemingway who owned a saloon. It soon became Hemingway’s favorite bar and today is a favorite of everyone who visits Key West.
Because of its history and tradition, Sloppy Joe’s attracts the liveliest crowds of visitors. Every PubClubbing tourist makes his/her way into here at least a few times during a trip. This is where they go to really cut loose in Key West. The music is good, the staff friendly and since it’s the largest of the pubs in town, there is plenty of room for dancing.
Sloppy’s is busy from Noon to well past midnight. For those who don’t ever care to leave, Sloppy Joe’s serves food. The bartenders are kept busy with the day-and-night crowd flows at Sloppy Joe’s.
Just down from Sloppy Joe’s on Front Street is the Hog’s Breath Saloon. This is a great “bonding bar” with an especially friendly staff that eagerly engages in entertaining conversations with patrons. As they say here, having hog’s breath is better than having no breath at all.
People headed for Sloppy’s usually stop first at the Hog’s Breath.
Further down the street is a Key West landmark. Captain Tony’s Saloon, made famous by the Jimmy Buffett song “Last Mango in Paris,” serves cold long-necks in an atmosphere surrounded by thousands of business cards from patrons of the past. The building is the original location of Sloppy Joe’s, where Hemingway met his third wife back in 1936. Or so goes the legend. One fact that is not myth is that Captain Tony’s patrons, fed up with local politicians, elected their favorite bartender (Tony) mayor of Key West some years ago.
Back on Duval Street, Rick’s Bar attracts a younger crowd than Hog’s Breath or Captain Tony’s. Rick’s serves frozen drinks in the coolest plastic cups in the Keys; the slogan is “As Time Goes By,” from the movie Casablanca. The place has several levels, including one with karaoke.
Parrot Heads will naturally flock to Jimmy Buffett’s Margaritaville Cafe (500 Duval). But it’s not on the radar screen of most locals or tourists in the know. The place is just too pristine – too clean and modern considering Buffett’s history in Key West. You kind of expect a place with dark wood, bad carpeting and pool tables. Unlike the bar, though, the gift shop is a Parrot Head’s delight. Occasionally, Coral Reefer or two pops into Margaritaville and Buffett himself did through the years.
About halfway up Duval (toward the Southernmost Point), The Bull is three levels of rocking and rolling. It’s largely a night place, best after 10 p.m. This old-time open-air bar features live music on the first floor, darts and pool on the second floor and has a clothing-optional third level.
Irish Kevin’s bar is fun time, and since PubClub.com’s Bartender’s first name is Kevin, he demands you go there. This is a very fun place that is likely to be a very frequent stop during any pubclubbing visit. The PubClub.com crew dispatched to Key West for New Year’s Eve loved this place, as these photos clearly demonstrate.
The crowd at the Bull is largely local sprinkled with Key West frequent travelers. Locals prefer a pair of pubs off Duval, the Schooner Wharf Bar (202 William St., near Caroline) and the Green Parrot (601 Whitehead near Mallory Square).
Schooner’s is a tiki-style bar with an open patio while the Green Parrot claims to be “the first and last bar on U.S. 1” which is true depending on one’s point of view.
The Green Parrot was once voted one of the Best Bars in America. It sells t-shirts with slogans like, “See the Lower Keys on Your Hands and Knees” and “No Sniveling.” At the Green Parrot, the management works tirelessly to avoid progress. To prove its point, the Parrot – as well as the Schooner – only accepts cash.
Watch out for those frozen drinks at Fat Tuesday! And for fun with live music, there’s Willie T’s, not to be confused with that British Virgin Islands bar of the same name.
Key West Daytime Bars, Outdoor Patios & Waterfront Hangouts
Forget sleep; there’s people to meet and places to party in the daytime, too.
It’s pretty much a given that any bar in Key West is open for business after Noon, but for an outdoor deck and a patio, these are the places to go.
Located on the water adjacent to the Pier House is the Ocean Key House. It’s one of the island’s premier hotels and has a popular late-afternoon bayside bar. Music is courtesy of Fritz and Lisa, a dynamic daytime duo.
A good place for lunch right on the harbor is Schooner Wharf, where it’s easy to sit back and have oysters and beer, every day of the year. Well, with an order or two of conch fritters, too.
Give me oysters and beer, every day of the year…
There’s a pool and outdoor bar at Dante’s in Conch Harbor Marina. This is the place to break out the bikins and board shorts and pretend as if you are on Spring Break (which, for most of March, a lot of people are, in fact).
Mallory Square Sunsets: A Key West Nightlife Tradition
Thousands gather on the dock at Mallory Square to see the sunsets.
If there is one “must-do” of Key West, it is sunset at Mallory Square (adjacent to the Ocean Key House at the north end of Duval).
Here, the disappearance of the sun is a ritual, toasted each and every day. The annual festivals are celebrated at other places. Thousands gather on the sidewalk each evening and are entertained by street performers, high-wire artists and others locals, many of whom earn their living doing this each evening.
There’s always a few sailboats going by to enhance the sunset photos.
It can get pretty crazy here, like the time a buxom parasailing girl had so much tequila she decided to yank off her top, prompting the skipper to drive the boat back and forth several times in front of the cheering crowd.
After sunset, have drinks at Casa Cayo Hueso or there’s usually a calypso band playing at the Sunset Deck at the Pier House.
Live Music In Key West: Local Bands, Musicians & Where To Hear Them
Follow the sounds of your favorite musicians and you are guaranteed to have a good time in Key West.
The musicians rotate from bar to bar in an island game of musical chairs, usually playing two to three gigs each day. As the day grows older, the bands grow larger and the names often change according to who is in the group. Fortunately, the lead singer’s name is usually included somewhere in the name, so it’s not difficult to figure out where who is playing.
The most popular are Fritz’s various bands (Ocean Key House Sloppy Joe’s when it’s known as the Robert Albury Band); Michael McCloud, kind of a modern-day/old-time Buffett who plays 60s and 70s rock mixed in with some “local” originals, unique songs about Key West (he’s a regular at Schooner’s) and blues singer Mike Lee. McCloud, who describes himself as “an alcohol-powered juke box” came to Key West for a weekend more than 50 years ago and has yet to leave. Keys Disease, indeed.
James T. Slater has the unoffical song of Key West called “Key West Address” while Howard Livingston has “Magic In Key West.”
These and other musicians play at bars all around town.
The key is to know the top musicians and keep track of their location either by asking them, the bartenders or through the weekly newspapers (Paradise This Week, Key West The Newspaper, Island News, L’Attitudes).
Or, one can hole up at one of the traditional pubs like Sloppy Joe’s or Hog’s Breath and wait for the entertainment to come your way.
Kevin Wilkerson is the founder of PubClub.com, an award-winning journalist and nightlife expert who has covered destinations, events and nightlife for more than two decades. While working as a newspaper reporter, he received an Associated Press award for investigative journalism. He has been to Key West several times.
Next Stops On The Key West Party Bus:
• The Nightlife Blogger In Key West!
• The Nightly Ritual Of Mallory Square Sunsets
• Oh My Gosh, I’ve Got Keys Disease!
• Key West Orientation & Visitor’s Guide