A Parrothead’s Guide to Remembering Jimmy Buffett in Key West
I was completely captivated by Key West the very first time I stepped foot on the island. And I wasn’t the only one. Jimmy Buffett was, too.
Key West gave Jimmy Buffett great inspiration which now inspires me as well as many others. It was hard to fall in love with the Key West lifestyle without also falling in love with Jimmy Buffett’s music. It’s like the two have always been connected.
The island’s influence on Jimmy Buffett helped him create countless songs that parrot heads have enjoyed throughout the years (and will continue to enjoy for years to come).
Key West is a small island that holds a big place in the heart of Jimmy Buffett fans. And Jimmy loved Key West back; returning many times to perform at places like the Key West Theater and the Coffee Butler Amphitheater.
Whether you’re visiting Key West to trace Buffett’s steps or just to soak in island life, these are the places that capture the essence of Key West’s connection to Jimmy Buffett. We will cover all of the key spots that every Buffett enthusiast should visit in Key West.
Louie’s
Louie’s is one of the best restaurants in Key West. It was also one of Jimmy Buffett’s favorite places. While the food speaks for itself, some claim that Jimmy Buffett is what helped Louie’s become famous. He lived next door at one time and would often sing there at Louie’s.
In the famous song Trying to Reason with Hurricane Season, he is referring to the Afterdeck Bar (a bar attached to Louie’s) when he says he “stumbled next door to the bar”.
Shrimpboat Sound Studio
Shrimp Boat Sound was a recording studio that Jimmy Buffett would occasionally use. It was kind of a “secret studio” of sorts, but he recorded many albums there. It’s located in Key West’s historic seaport. The historic seaport in itself will make you feel you are living inside of a Jimmy Buffett song.
The studio used to be a shrimp storage cooler and it still looks like one. It’s really small and was once indiscreet but since his death, it’s actually hard to miss. That’s because it is now covered in stickers from people who have traveled from all over to pay respects.
You’ll likely find it as you wander the area but if you’re looking to walk there directly, it’s where Green Street and Elizabeth Street meet. You can see it easily from the Conch Republic.
The Chart Room Bar
The Chart Room Bar is a total hidden gem in Key West in the Pier House Resort & Spa. It is a hotel room that was converted into a bar. What is now the Pier House Resort and Spa was built around it. The short version is that it is credited as the place Jimmy Buffett got his start.
But the longer version is that it’s said to be the first stop Jimmy Buffett made when he first came to Key West with Jerry Jeff Walker. This is referenced in his song Tin Cup Chalice. Jimmy Buffet spent a lot of time at the Chart Room, especially in his early years.
It’s said that Jimmy Buffett would perform here in exchange for drinks.
Jimmy Buffet wrote his song A Pirate Looks at 40 about one of the bartenders of the Chart Room bar. He also met his wife Jane there.
Even without its direct ties to Jimmy Buffett, the Chart Room has authentic island written all over it. It’s a small, casual spot covered in vintage photos and eclectic decor.
To this day, you can get free hot dogs, peanuts, and popcorn. It’s been this way since the bar opened in 1969.
Finally, The Pier House, where the Chart Room is located, was also used as a filming location for Jimmy Buffett’s songs One Particular Harbor and Who’s the Blonde Stranger.
Margaritaville
The Margaritaville restaurant has pictures of Jimmy Buffett the walls, his music playing, island-inspired food, and a laid back atmosphere.When Jimmy Buffett used to be in Key West, he’d often pop in for a surprise/unannounced concert there.
With so many Margaritavilles now, something unique about Margaritaville Key West is that it was the very first one!
Location: 500 Duval St
Original Margaritaville store location
Jimmy Buffett’s Margaritaville is located on Key West’s Duval Street but it was originally a retail store on Margaret Street. Today it is home to Local Color, a clothing store. It wasn’t open long because it relocated to the location of the restaurant on Duval Street after the restaurant proved successful.
Location: 276 Margaret St
Fausto’s Food Palace
In Jimmy Buffett’s song called My Head Hurts, My Feet Stink, and I Don’t Love Jesus, he says, “I’m goin’ down to Fausto’s get some chocolate milk”. In that song, he is referencing this grocery store, which is the oldest running Key West business. It opened in 1926.
Location: 522 Fleming Street – note that there are two Fausto’s in Key West and you want the one on Fleming
Antonia’s
Antonia’s is now an Italian & Mediterranean restaurant but it was once Crazy Ophelia’s, where Jimmy performed one of his first concerts.
Key West Library
If you visit the Florida Keys History Center collection at the Key West library, you can see a letter written by Jimmy Buffett. The letter is dated October 22, 1984 and thanks the library for inspiration and air conditioning.
Places Jimmy Buffett Used to Live
If you ever wondered whether Jimmy Buffett loved Key West or not, you don’t need to look much further than all of his addresses. Jimmy Buffett was a Key West resident for years at a number of different addresses.
123 Ann Street
This was Jimmy Buffet’s first Key West home. He lived in the guest house at 123 Ann Street; the apartment was rented from Thomas McGuane, who would become a lifelong friend (he also married Jimmy Buffett’s sister!) Today 123 Ann Street is home to Captain’s Corner Dive Shop.
Location: 123 Ann Street
Jimmy’s apartment at 704 Waddell
704 Waddell Street was located right next to Louie’s Backyard (literally, two doors down), the restaurant mentioned above. Today, this address is home to the Coconut Beach Resort. When this was Jimmy Buffett’s home, he often visited Louie’s next door as mentioned above. This is also where he wrote many of his most beloved songs.
Captain Tonys
It’s almost impossible for me to even hear “Captin Tony’s” without thinking of Jimmy Buffett. My mind instantly starts singing the lyrics, I went down to Captain Tony’s / to get out of the heat… This is from his song The Last Mango in Paris (this is one of my favorite songs!)
This is a historic bar in Key West on its own but it was also a popular spot for Jimmy to play in the earlier days of his career. And like many places on this list, the bar itself makes you feel like you’re living a Jimmy Buffett song with its memorabilia and history (it was the original Sloppy Joe’s restaurant).
Location: 428 Green Street
Caroline Street
Jimmy Buffett has a song titled There’s a Woman Going Crazy on Caroline Street. It’s debated whether the woman actually existed or whether it was just made up.
B.O.’s Fish Wagon
B.O.’s Fish Wagon is a short walk from the Shrimpboat Sound Studio. It is said that the Coral Reefer Band grabbed lunch from here when they were taking a break from recording.
Location: 801 Caroline St
Mallory Square
You can’t really visit Key West properly without visiting Mallory Square. While there isn’t anything to directly tie Jimmy Buffett to Mallory Square now, it’s a good spot to remember him. He used to play there for free with the street performers. You can still find street performers there today (Mallory Square is one of the best free things to do in Key West).
Location: 420 Wall Street
Red Garter Saloon
The Red Garter Saloon is now an adult entertainment club. But it was The Snake Pit when Jimmy Buffett visited. There was some writing on the bathroom wall, “life and ink run out at the same time. -Squid” that Jimmy Buffett used as inspiration in his song “If I Could Just Get it on Paper”.
Location: 208 Duval St
Blue Heaven
Blue Heaven is one of the most popular places to get breakfast in Key West. And Jimmy Buffett must have loved it, too, since it inspired the song “Blue Heaven Rendezvous”.
Location: 729 Thomas St
Key West Fire Department
You might not necessarily visit this location, but Jimmy Buffett used to wear a t-shirt at concerts that said, “Where is Bum Farto?”
I shared this story when I covered haunted places in Key West, but basically Bum Farto was a fire chief in Key West. He was a drug dealer and one day completely disappeared.
Not only did Jimmy Buffett don a shirt wondering where Bum Farto could be, it also inspired the lyrics, “bum’s down in Capo’s, he’s just having a ball, what would they do on another landfall,” in his song Landfall.
Location: 1600 N Roosevelt Blvd
Temporary Bonus: Sand Sculpture
Across from Louie’s there is a sand sculpture of Jimmy among some others we also mourn, including Toby Keith. I’m not entirely sure of the story – who made the sand sculpture or how long it will be there. But it has been there for quite some time now.
They also take good care of the sculpture. When we visited, we had two days of some pretty nasty weather and they wrapped up the sculpture to protect it. While I’m sure it won’t be there forever, hopefully it will be there long enough for you to see it and enjoy.
A lot of people were affected by the death of singer-songwriter Jimmy Buffett. While we grieve his death, his memory will live on through his songs (and Margaritaville). Key West is a great place for parrot head fans to remember him and hopefully this guide helped give you some ideas on some of the best places to visit to remember Jimmy Buffett.
