10 No Name Pub
The No Name Pub has been sitting on Big Pine Key since the 1930s. It was once a small general store complete with a bait and tackle shop until the owners saw an opportunity. They brought in beers and sandwiches and by the 1940s, they converted the upstairs into a brothel. Eventually, all these extravagant extras were shut down and all that remains is the quaint rustic pub that is known for its pizza and beer.
9 The Green Room
This eco-friendly bar is at the heart of Key West's party scene. They offer a plethora of all-natural frozen drinks for patrons to enjoy while listening to their ongoing ream of live music. You can't miss it with their neon green-lighted front and the line of locals and tourists spilling out of the front door.
They're known for their sustainability efforts; they recycle all their used items and offer merchandise proceeds to places such as the Turtle Hospital. Even the bar is made out of a tree that fell in 2014!
8 Captain Tony's
Key West is full of colorful history, and Captain Tony's Saloon is no exception. The building has been around since 1852, serving as an ice house, a morgue, and a telegraph station. After it had been recommissioned into a watering hole, it became the home base for famous guests. This is where writers such as Ernest Hemingway. Shel Silverstein, and Tennessee Williams set up shop, along with notables such as Jimmy Buffet. In fact, every time a new celebrity comes in, they get their own bar stool with their name on it.
You'll notice the "Hanging Tree" in the middle of the bar is where 17 people lost their lives. There is also a massive amount of license plates, dollar bills, and bras hanging like chandeliers from the bar's ceiling.
7 Shots and Giggles
This intimate bar is a great stop if you want to feel like the locals do. They have liquor and wine, but they're known for their selection of craft beers. They don't serve any food, but you know you're really only to go here for the shots. They have a wide selection of premium options, which their friendly staff will be more than happy to mix up for you. We also recommend trying their mermaid water.
Shots and Giggles is tucked away on Ann and Greene Street right next to the Tattoos and Scars Saloon.
6 The Bull and Whistle Bar
This open old-school bar is celebrated for their potent cocktails. Downstairs at the Bull, you'll find a hand-painted mural that tells the history of this long-standing pub.
Upstairs at the Whistle Bar, you'll be welcomed by ongoing entertainment and tropical devices. There's an incredible view of Old Town Key West from their balcony seating where you can sit and watch the sunset while you drink a classic Dark and Stormy.
5 The Rum Bar
Even if you aren't staying next door at the Speakeasy Inn, the Rum Bar is a perfect spot to hit up after a day on the beach. It's just a short distance from the shore, located at Key West's southernmost point. With over 350 rums, you'll have your work cut out for you, but they're famous for their Painkiller Cocktail.
The Rum Bar is the former home of famous former cigar selector, Raul Vaquez, who decided his passion for rum-running would be of better use to the locals of the Florida Keys.
4 Tree House
Located directly above the Green Room is one of the Key's newest and most unique tavern: The Tree House. This open-air bar lets its visitors enjoy fresh coastal air while sipping on tropical libations and listening to live music.
There's always something going on in the Tree House and is quickly becoming the Key's best-kept secret.
3 The Smallest Bar
The Smallest Bar in Key West holds fast to its name. This is more of a token stop than anything, but its a bar you won't regret visiting. This kitschy little store is quick to serve tropical drinks in their 72-square-foot watering hole. There are only four bar stools and one person that plays bartender right next to the Smallest Bar Inn where you can stay for a prime spot on Duval Street.
2 Sloppy Joe's
It was Ernest Hemingway who gave this pub its name. Sloppy Joe's is another Key West mainstay that has seen its fair share of guzzling guests since its early days in the 1930s. It was owned by Joe Russel who ran it as a speakeasy until the Prohibition era lifted. After that, Hemingway enticed his friend to rename the bar to Sloppy Joe's owing to the come-as-you-are atmosphere and the fact that his floors always seemed to be a mess.
Sloppy Joe's is a must for Key West newcomers, while regular Key West visitors already know to make this pub their first stop.
1 Alabama Jack's
Alabama Jack's is a seaside spot that has a welcoming breeze and even better seafood. Located in Key Largo, this bar is enjoyable day or night, with an unyielding supply of conch fritters and cold drafts.
As per usual with any Key West bar, this watering hole hosts live music which draws in quite a crowd. It's a simple little shack situated just off the main road, but Alabama Jack's is a pit stop that should definitely be added to your bucket list.