SoutheastFood & DrinkIslands

The 4 Most Legendary Bars of Key West, Florida

By , November 24th, 2014

Key West is an island known for its beaches and the laid back ambianceBut after a night out in Key West, it will be no wonder legends such as Ernest Hemingway and Jimmy Buffet got caught up in the nightlife and didn’t want to leave this unconventional island. If you’re traveling to the Florida Keys, you cannot miss Key West. You can still visit these bars that have become an integral part of the island’s historylegendary for the locals and a must visit for anyone arriving to this eccentric place.

Drink at Hemingway’s storage closet

Sloppy Joes Bar, Key West, Florida
Photo by  Marina Kuperman Villatoro 

1. Sloppy Joe’s — The official record says that Sloppy Joe’s opened in 1933 but it actually opened in 1851 where Captain Tony’s (#3) is located today. This bar was one of Hemingway’s favorites. He and the owner not only became great friends, but Hemingway trusted Joe Russell so much that when he left for Cuba he left a lot of his personal things stored in a storage room in the back of the bar. Many of those things are now displayed on the walls.

Fun fact: The reason why Sloppy Joe’s moved to its actual location was over a silly dispute with the landowner. The guy wanted to raise the rent for the amount of $1 so Joe moved the bar in the middle of the night, not even bothering to close the place and had the customers help him to carry the furniture!

sloppy joe's entrance Key West
Photo by  Marina Kuperman Villatoro 

An open-air-hipster-watering-hole

green parrot bar, key West, Florida
Photo by John W. Penney

2. Green Parrot — This is a small bar that started as a grocery store in 1890. It  became the place for Cuban and Bahamian immigrants to meet up and shop for their traditional meals. Soon after, the back room became a place where local musicians gathered for jam sessions that would last all night long. When World War II began the grocery store became The Brown Derby Bar, a bunker-like, air conditioned hangout for submarine sailors. That’s why sailors from the 60’s still visit the place when visiting Key West. During the 70’s Key West became a haven for free spirits and the bar was turned into The Green Parrot Bar, an open-air hipster watering hole.

The hangout hole for Truman Capote, Tennessee Williams, and Shel Silverstein

Captain Tony's Wall, Key West, Florida
Photo by  Marina Kuperman Villatoro 

3. Captain Tony’s — This bar/restaurant is famous for its history and décor. It was first opened in 1851 and became a fixture for people like Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein and Jimmy Buffet. A guy called Joe Russell took over the place and that’s how the original Sloppy Joe’s was born. You could find Hemingway with a drink, chatting and having a good time. This is also where Jimmy Buffett got started playing and would often be paid in tequila. The original Captain Tony was one of Key West’s most colorful characters. He was the father of thirteen children by five wives. During the 1960’s Captain Tony became a gunrunner for the U.S. government in support of Cuban mercenaries during the Bay of Pigs invasion.

Captain Tony's Bar, Key West, Florida
Photo by  Marina Kuperman Villatoro 

Waste away again in Margaritaville

Jimmy Buffet bar Key West, Florida
Photo by Mike

4. Margaritaville — When Jimmy Buffet started getting paid in real cash, he didn’t want to leave his beloved Key West behind so he started the original Margaritaville in 1985. He arrived to Key West with a broken heart and found a bunch of great people in a laid back place that welcomed him with open arms. But most importantly, he was able to grow as an artist here.  Margaritaville is a fun café during the day that turns into a full-on live music bar and restaurant where you can grab a drink and spend the night. You can really feel the spirit that gave birth to this whole chain of restaurants. Plus, you get to learn the history of the place and hear stories from its earlier days. And we never truly tire of Jimmy Buffet and his music.

Where to Stay in Key West

Chelsea House pool

Now that we’ve got you hooked on the idea of visiting Key West, here’s a look at our recommendation for where to stay. Check out the Chelsea House, right in the heart of Old Town. The property consists of two estates constructed in Victorian and Queen Anne Styles, surrounded by tropical gardens and those postcard palm trees, offering a bit of a shade over the pool. When you’re ready to get back out there, you’re just two blocks from bustling bar-hopping favorite, Duval Street.

Aside from having a fun history, each of these bars offers a great ambiance, good food and tasty drinks. It is worth paying a visit to each of these while you visit Key West, even if it is just for a photo op.