Key West is known for many things — sun, colorful history, and some of the best bars that someone can fit on a tiny island.

Dive bars are some of our favorite places to visit when we are looking for a drink. You get a chance to meet local people, try new activities, and feel local charm. Key West has not only amazing dives to explore but also fabulous stories that go alongside their bars. Read on for our favorites!

Capt. Tony’s Saloon

428 Greene Street

Capt. Tony’s has been many different things since it first opened in 1851 — an ice house, morgue, telegraph station, cigar factory, club, speakeasies, and the original Sloppy Joe’s. It is also home to a hanging tree, which you can check out right next to the pool tables.

In 1933, a local Key Wester, Joe Russell, turned the then vacant speakeasy into a bar. He and his friend, Ernest Hemingway, decided on the name Sloppy Joe’s and it quickly became a local favorite. In 1937, the landlord raised the rent by $1 per week and, in protest, the owner and patrons, including Hemingway, moved the entire bar to 201 Duval Street, where Sloppy Joe’s still resides today!

In 1958, Captain Tony Tarracino, a local boat captain, bought the bar and renamed it for the last time as Captain Tony’s Saloon. In the 70’s, Jimmy Buffett got his start in Key West and on the stage of Capt. Tony’s Saloon and apparently, they paid him in tips, beer, and tequila! Take a shot and hum Last Mango in Paris, the song that Buffett wrote about his experience there.

When you visit now, the ceiling is covered in bras (a mystery we did not solve, so let us know if you know why!) and stools are painted with the names of each famous person that sat on them (Truman Capote and JFK, to name a few).

If you are in Key West, you should definitely get a drink at this history-rich, quirky dive bar!

Sloppy Joe’s

201 Duval Street

Picking up where our history lesson left off… Sloppy Joe’s was reborn with the help of Hemingway and the mob of devoted patrons of Joe Russell’s bar on Duval Street and remains an incredibly popular and always busy bar today. Hemingway made the new Sloppy Joe’s his regular bar and even called himself a co-owner.

It is home to the annual Papa Look-Alike Contest, a mid-July festival of Hemingway enthusiasts crowning the person who’s appearance best resembles the great American novelist’s likeness and judged by past winners.

Sloppy Joe’s has live music, a huge bar, incredibly friendly wait staff, and walls adorned with history. It is open 365 days per year, so no matter when you visit, you will be able to come have some casual food and drinks from their huge menu!

Hog’s Breath Saloon

400 Front Street

Hog’s Breath Saloon opened in 1988 and isn’t unique to Key West, but this location definitely has its own Key West flair.

Roosters walk through the amazing outdoor seating and live music makes their incredibly tasty (and affordable!) drinks even tastier. There’s a great raw bar, a fun license plate collection, and an overall atmosphere that makes it easy to spend an entire evening here!

The Green Parrot

601 Whitehead Street

The Green Parrot is simply the quintessential Key West bar. If you are in Key West, you absolutely must dedicate an evening to this bar that boasts a music schedule that is sure to entertain anyone. It has been cited by Zagat as the Best Music/Performance Venues in South Florida, and it really is.

The walls are covered with music memorabilia, and the open-air bar lends itself to casual drinks served by no-nonsense bartenders. Take an iconic selfie next to the painting called Smirk and enjoy some fantastic music.

This bar started as a grocery store with a small space in the back for musicians to share their talent in 1890 and has become an iconic Key West watering hole that you have to experience for yourself!

The Galleon Sunset Tiki Bar

617 Front Street

Even though this isn’t truly a dive bar, I couldn’t end this post without mentioning one of the best views of Key West’s sunsets. If you want to spend an evening admiring the most beautiful sunset you will ever see and try to catch the green flash, then enjoy some drinks and live music at the Galleon Sunset Tiki Bar.

People show up hours before the sunset to stake out a great spot for viewing the final hours of the day. This is by far my favorite place to see the sunset every day, and I will bring a book and drink a few piña colavas (a twist on the original adding raspberry purée). Be sure to look up sunset times in advance and arrive early!