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Famous Bars & Their History
My own favorites include Willie T’s, Bali Bar and Green Parrot soundcheck with the locals. I also love General Horseplay and a Martini Monday at Virgilio’s. The people, music and familiar faces are a big part of why I keep going back. Below are the old stories, newer favorites and a little television trivia.
Schooner Wharf Bar
Paul and Evalena Worthington arrived in the Key West Bight aboard their schooner Defiance in 1984 and opened the open-air bar in 1986 on the site of the Singleton Shrimp factory. Its waterfront setting keeps the old working-seaport story close at hand.
Visit Schooner Wharf Bar website
Captain Tony’s Saloon
The 1851 Greene Street building served as an icehouse, city morgue, telegraph station, cigar factory, and a saloon. Joe Russell opened the first Sloppy Joe’s there in 1933. After that bar moved to Duval Street, Captain Tony Tarracino bought the Greene Street bar in 1958 and gave it his name; Jimmy Buffett played there in the early 1970s.
Visit Captain Tony’s Saloon website
The Chart Room
This intimate Pier House bar became a gathering place for locals, visitors, and musicians. Jimmy Buffett has credited it as his first gig, playing for drinks and tips when he arrived in Key West in the early 1970s.
Rick’s and Durty Harry’s
Mark Rossi established the Duval Street entertainment complex in 1984. Its growth reflects the modern nightlife era on Duval, where live music, dancing, and late-night venues joined the island’s older saloon traditions.
Visit Rick’s and Durty Harry’s website
The Green Parrot
My pick: soundcheck with the locals. The Green Parrot is one of my favorite places to hear music and settle into the island’s rhythm. Check its calendar for the day’s soundcheck and evening shows.
Antonio Sanchez opened a grocery store on the Southard and Whitehead corner in 1890. It became the Brown Derby, a Navy sailors’ bar during World War II. Judy Sullivan later renamed it the Green Parrot and shaped it into a free-spirited neighborhood music venue; bartender and artist Saul Paul Stewart painted its “Smirk.”
Visit The Green Parrot website
Sloppy Joe’s
Joe Russell opened his bar on December 5, 1933, after Prohibition ended, at 428 Greene Street. Ernest Hemingway was Russell’s close friend and a regular. In 1937, after a rent dispute, Russell and his customers moved the entire bar overnight to its present Duval Street location.
Hog’s Breath Saloon
Jerry Dorminy started the saloon in Fort Walton Beach in 1976 and brought it to Key West in 1988. It grew into a familiar Duval Street stop for live music and the island’s casual, anything-goes bar culture.
Visit Hog’s Breath Saloon website
Don’s Place
A neighborhood bar on Truman Avenue, and a reminder that Key West’s bar scene reaches well beyond Duval. Don’s belongs in the island story as a local gathering place—and now as a filming location. Season two of Apple TV’s Bad Monkey filmed scenes here in 2026.
Read the Florida Keys filming update.
Half Shell Raw Bar
Seafood, a drink and a view of the Historic Seaport: Half Shell is one of those places where the setting is part of the experience. It also joins Don’s Place on the Bad Monkey season-two location list. Watch the show and see whether you recognize your harbor stop.
Half Shell’s current menu and details · Filming story
Bali Bar
One of my favorite newer additions to Key West. I love this bar. Tucked inside The Key West Hotel on Duval Street, it brings a tropical courtyard feel and cocktails to an evening out. It has already earned a spot on my own short list.
Willie T’s
Willie T’s is another personal favorite when I want music and a fun Key West night. Pair it with a wander along Duval, then follow the music. Check the venue’s lineup for the day you are going.
General Horseplay
I love General Horseplay’s atmosphere, cocktails and music. Zach Lovering is one of the musicians I like to catch. Schedules move around, so check the current lineup rather than assuming a favorite performer is there every night.
Music and updates at General Horseplay.
Virgilio’s: my Martini Monday
Behind La Trattoria’s Old Town restaurant, Virgilio’s is one of my favorite Monday-night stops: martinis, dancing, good food and familiar faces. I enjoy Ross Brown and Randy Stindt, and the room often has that everyone-knows-each-other feeling. La Trattoria’s rectangular bar is a great place to meet locals too.