Most Iconic Bars on Duval Street – Key West’s Must Visit
Last Updated June 23, 2026
If you’ve ever walked down Duval Street in Key West, you already know it’s one wild, fun, history-packed strip.
Some of the most famous bars in the whole country are right here, all within a few blocks of each other. Some go back almost 100 years. Some are tiny. Some are huge. All of them have a story.
Here’s your guide to the most iconic bars on Duval Street, what makes each one special, and why you should stop in.
(Pssst — if you’d rather watch than read, check out our YouTube Short that covers all these bars too!).
1. Sloppy Joe’s
Address: 201 Duval St, Key West, FL 33040 Opened: December 5, 1933 (moved to this Duval Street spot in 1937)
Sloppy Joe’s might be the most famous bar in Key West, and there’s a good reason for that — it was Ernest Hemingway’s favorite hangout.
The bar actually started across the street under different names before settling into its current spot on the corner of Duval and Greene. There’s live music almost all day, every day, and the walls are covered in old photos and Hemingway memorabilia.
Why visit: It’s basically a piece of Key West history you can sip a drink. Try the famous Sloppy Joe sandwich, listen to live music, and keep an eye out for Hemingway look-alikes if you’re there in July.
Few people visit Key West and don’t go to Sloppy Joe’s!
Most Popular Bars Video
2. Rick’s, Durty Harry’s & the Tree Bar (Rick’s Entertainment Complex)
Address: 202 Duval St, Key West, FL 33040 Opened: 1984
These three are technically one giant complex, so we’re grouping them together.
Rick’s Downstairs has karaoke and cheap drinks, Rick’s Upstairs has a huge dance floor and a balcony over Duval Street, Durty Harry’s brings live rock bands every night, and the Tree Bar is the chill outdoor spot shaded by a big tree, known for fresh-squeezed juice drinks.
Why visit: If you want a one-stop party with something for every mood — dancing, live bands, karaoke, or just relaxing under a tree — this complex has it all.
3. Willie T’s
Address: 525 Duval St, Key West, FL 33040
Willie T’s is an open-air bar and restaurant smack in the middle of Duval Street, which makes it one of the best spots for people-watching. It’s got live music every single day and is known for its mojitos and surprisingly good food (don’t skip the conch fritters).
Why visit: Great food, great drinks, and a front-row seat to all the Duval Street action. It’s a perfect lunch-into-evening kind of stop.
4. The Bull (Bull & Whistle Bar)
Address: 224 Duval St, Key West, FL 33040
The Bull is one of the last old-school open-air bars left on Duval Street, and the building itself goes back to the early 1900s, when it was a boarding house and later a Prohibition-era speakeasy. The walls are covered in hand-painted murals of Key West legends like Hemingway and Tennessee Williams.
Why visit: Live music every night downstairs, a rowdy game bar called the Whistle upstairs, and (if you’re brave) an adults-only third floor. Don’t miss the coin-operated breathalyzer on the wall.
5. Hog’s Breath Saloon
Address: 400 Front St, Key West, FL 33040 Opened: 1988 in Key West (the original Hog’s Breath started in Fort Walton Beach, FL in 1976)
Hog’s Breath has one of the most famous slogans in Key West: “Hog’s Breath is better than no breath at all,” which came from the founder’s grandmother. It’s known for nonstop live music (three bands a day, basically every day for almost 50 years) and a laid-back open-air vibe.
Why visit: Great seafood, cold drinks, and you’ll probably walk out with one of their famous t-shirts — they’re practically a souvenir tradition at this point.
6. The Smallest Bar
Address: 124 Duval St, Key West, FL 33040 Opened: 2000
This one lives up to its name. At just 72 square feet — about the size of a jail cell — it’s considered the smallest bar in the entire United States. It only has two stools, but somehow it still manages to pack people in for a quick, fun stop.
Why visit: It’s a “you have to see it to believe it” kind of spot. Perfect for a quick photo and a cold drink while you’re bar-hopping down Duval.
7. La Te Da
Address: 1125 Duval St, Key West, FL 33040 Opened: 1975 (the building itself was built in 1892)
La Te Da is part hotel, part restaurant, part bar, part cabaret — and it’s a Key West landmark with a really cool history. The building used to belong to a cigar manufacturer named Teodoro Perez, and Cuban revolutionary Jose Martí actually gave a speech from its balcony back in 1883. Today it’s known for live entertainment, a piano bar, and its famous Sunday Tea Dance.
Why visit: Great food, a beautiful poolside bar, and some of the best live entertainment on the island. It’s a long-standing favorite in Key West’s LGBTQ+ scene too.
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8. Captain Tony’s Saloon
Address: 428 Greene St, Key West, FL 33040 Opened: 1958 (the building itself dates back to 1851!)
Here’s a fun twist: this is actually where the original Sloppy Joe’s used to be before it moved down the street. The building has had a wild past — it’s been an ice house, a morgue, a telegraph station, and even a speakeasy. In 1958, Captain Tony Tarracino bought it and gave it his name. A young Jimmy Buffett used to play shows here for tequila instead of cash!
Why visit: Look up — there’s a real tree growing right through the middle of the bar, plus a creepy “hanging tree” legend. Every barstool with a celebrity’s name painted on it has its own story.
Map of Most Iconic Bars on Duval Street
Most Popular Bars on Duval Street – Honorable Mentions
Irish Kevins – Just a few steps south of Sloppy Joe’s. Known for its irreverent entertainment. Not a place for kids or your 85-year-old grandmother!
The Chart Room – In the Pier House Hotel at 0 Duval Street. We hate to even mention it because it is already too crowded most days (opens at 4 PM).
801 Bourbon Bar – Known for bourbon and LGBTQ hangout.
Jack Flats – Locals love this sports bar. Great for reasonable prices and the big game.
Quick Tips for Your Duval Street Bar Crawl
- Most of these bars are within easy walking distance of each other, so you can hit several in one afternoon or evening.
- Live music is a big deal here — almost every bar on this list has it daily.
- Bring cash for tips and souvenirs (a lot of these places sell their own famous t-shirts).
- Pace yourself! Duval Street is a marathon, not a sprint.
FAQs About Duval Street Bars in Key West
What is the most famous bar on Duval Street in Key West?
Sloppy Joe’s at 201 Duval Street is widely considered the most famous bar on Duval Street. It opened in 1933 and was the favorite hangout of Ernest Hemingway. It features live music daily and is listed on the National Register of Historic Places.
What is the oldest bar in Key West?
Captain Tony’s Saloon at 428 Greene Street is considered the oldest bar in Key West. The building dates back to 1851 and has served as an ice house, morgue, telegraph station, and speakeasy before becoming Captain Tony’s in 1958. It was also the original location of Sloppy Joe’s before it moved to Duval Street.
Did Ernest Hemingway really drink at Sloppy Joe’s in Key West?
Yes! Ernest Hemingway was a regular at Sloppy Joe’s throughout the 1930s and became close friends with the owner, Joe Russell. The bar holds an annual Hemingway Look-Alike Contest every July as part of the Hemingway Days celebration.
What bars are on Duval Street in Key West?
Some of the most iconic bars on Duval Street include Sloppy Joe’s, Rick’s Bar, Durty Harry’s, Willie T’s, The Bull, the Tree Bar, and the Smallest Bar. Hog’s Breath Saloon and La Te Da are also nearby classics that are must-visits on any Key West bar crawl.
What is the smallest bar in the United States?
The Smallest Bar in Key West, located at 124 Duval Street, is considered the smallest bar in the United States. It measures just 72 square feet — about the size of a jail cell — and has only two bar stools.
Where did Jimmy Buffett get his start in Key West?
Jimmy Buffett got his start playing live music at Captain Tony’s Saloon at 428 Greene Street in the early 1970s. He was often paid in tequila instead of cash. He later immortalized Captain Tony and the bar in his song “Last Mango in Paris.”
What is the best bar on Duval Street for live music?
Several Duval Street bars offer live music daily. Sloppy Joe’s has live music from morning until close. Durty Harry’s (part of the Rick’s Entertainment Complex at 202 Duval St) is well known for live rock bands every night. Hog’s Breath Saloon at 400 Front Street books three live acts per day.
Is Duval Street good for a bar crawl?
Absolutely. Duval Street is one of the best bar crawl streets in Florida. Most of the iconic bars are within easy walking distance of each other, many are open-air, and almost every spot has live music. The street runs from the Gulf of Mexico to the Atlantic Ocean, so you can literally bar crawl from one ocean to the other.
What should I drink at Hog’s Breath Saloon in Key West?
Hog’s Breath Saloon is known for cold beers, frozen drinks, and a raw bar with fresh seafood. Their signature Hog’s Breath Lager is brewed specifically for the bar and is a must-try. The laid-back outdoor setting makes it a great spot to settle in for a while.
What is La Te Da known for in Key West?
La Te Da at 1125 Duval Street is a historic hotel, restaurant, piano bar, and cabaret venue. It’s known for nightly live entertainment, its Sunday afternoon Tea Dance by the pool, and a long history tied to Cuban revolutionary José Martí, who gave a speech from the building’s balcony in 1883. It’s also a beloved fixture in Key West’s LGBTQ+ community.
More About Key West
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