Key West, Florida is without a doubt one of the places one MUST visit when checking out the Florida Keys. This is where most of the action has been taking place for the last 500 hundred years and is still going strong. It is popular among travelers because it has the highest average temperature in the United States, it never gets frost, and because the third-largest coral reef in the world is off the coast of Key West.
But it is also with a long and interesting history that includes: being the place where Ponce De Leon landed, being a popular place among pirates, getting independence from the US and once home to Ernest Hemingway, among others.
There are a few restaurants that have been around for a long time and have become part of Key West’s history. They became legendary for locals and a must visit for anyone visiting this eccentric place.
3 Key West Famous Restaurants
Of course, the food and ambiance in these three places are perfect, but there is what makes a must-visit in Key West.
1. Margaritaville Restaurant Key West
This is now a popular chain of restaurants owned by Jimmy Buffett. Up to this date, there around twenty five of the “Margaritaville” restaurants that spread all over the world. It is a fun café where you can find good food and a lot of merchandise from Jimmy Buffett.
However nothing beats visiting the original. The reason? It is a place where 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.
2. Sloppy Joe’s
The official record says that Sloppy Joe’s opened in 1933, but in reality, it had been around for a long time during the prohibition. (It is said that in Key West the prohibition wasn’t taken seriously.) The place was one of Hemingway’s favorites. He trusted the owner so much that he left a lot of his personal things stored in a room next door from this bar. After Hemingway’s death, some of that stuff has started being displayed on the walls.
Fun fact: Sloppy Joe’s original location is where Captain Tony’s Saloon is located now. After a dispute with the landlord of 428 Greene Street over a $1 rent increase the owner decided to move the entire bar in the middle of the night.
Related Read: Best BBQ in the United States
3. Captain Tony Key West
This bar/restaurant is famous for its history and décor. It was first opened in 1851 and became a favorite for famous people like Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein and Jimmy Buffet.
Within the property you will find what is called “the hanging tree”, a place where pirates used to be hung for their crimes, even a woman who murdered her husband was hung here. Some say that her spirit still haunts the saloon.
Inside Captain Tony’s Saloon – Leave a BraKey West is a perfect place for a fun beach vacation. There are tons of fun places to visit, like the above mentioned restaurants as well as a varied array of hotels that visitors can choose from. There are tons of fun and historic facts waiting for you on every corner.
Marina, I worked in the Keys one summer and I loved going to Key West for sunset and Key Lime Pie.
Thanks for the great memories and ideas on where to eat next!
Lisa Niver
We Said Go Travel
Didn’t know that about Captain Tony’s actually….
stay adventurous, Craig
Hi Marina,
In 1969-1974 I visited Key West, long before it became what it is today. Back then there was a bar called “(The) Shipwreck Inn” but I cannot find anything about it for a few online hours now. Do you know anything about it?
Thanks,
Greg
Hi Greg,
I don’t remember seeing it there either, unfortunately, we were supposed to be there for several days, but the 2nd day was horrible downpour and we left early, so we didn’t explore everything we intended to.
Well this looks like one that only a person who was there in those days– 1969-74, could help with. It’s probably gone for decades and didn’t make the cut for an historical landmark, much less remembrance.
One last thing is that about 10 years ago someone was selling T-shirts with the name Shipwreck Inn and a graphic of the street view of it online (ebay?). Not a tourist attraction even then, it was what today would be called a dive, and shrimpers would come in after being asea for weeks and the money would flow and the music, and times would roll. A real piece of hard working Americana, like cowboys in the early west. Certainly not a family place, it was just exciting to be there if you were young, adventuresome, or both. Maybe Jimmy Buffett would remember it, or someone in the Capt. Tony’s or Sloppy Joe’s ownership. I can try them.
Thanks.
Hey Greg,
How interesting!!! THere is definitely a lot of fun history on this island and I’m sure Jimmy Buffett and Hemingway can tell us a thing or two about this place.
There is a shipped wreck bar in Clearwater beach … if your ever out this way