Jimmy Buffett’s Key West: Places, Stories, and Songs
When Jimmy Buffett rolled into Key West in the early 1970s, catching a ride from Jerry Jeff Walker, he found something unexpected. Not just the parties and pirates people talk about, but an island where shrimpers shared bars with smugglers, where a beer could buy a story, and where every street hummed its own tune. Looking back on those years, he told TIME in 1998, “Back then I was havin’ such a good time bein’ me. I was like a flower in bloom.”
Chart Room at the Pier House: Where Everything Started
Friends steered Jimmy Buffett to the Chart Room at the Pier House in the early 1970s. This tiny room, more like a ship’s cabin than a bar, sits at the center of lore around his early storytelling
voice. Locals often link bartender Phil Clark and the room’s intimacy to the barroom storytelling behind “A Pirate Looks at Forty.” The scale hasn’t changed much. Regulars become stories, the bartender knows everyone’s business, and conversations still sound like verses waiting for a melody. To quote Jimmy: “Wrinkles will only go where the smiles have been.” This room has collected its share of both.
“I made enough money to buy Miami, but I pissed it away so fast.”
— A Pirate Looks at Forty
Captain Tony’s Saloon: The Last Mango Standing
The stories at Captain Tony’s still hang in the air. Buffett played here in the early 1970s, was often paid in tequila, and he immortalized both the bar and Tony Tarracino in “Last Mango in Paris.”
“I went down to Captain Tony’s to get out of the heat.”
— Last Mango in Paris
The bar still operates with the same philosophy that attracted Buffett. If these walls could talk, they’d sing.
The Song That Almost Got Away
Here’s a story that captures everything about Buffett’s relationship with the Keys: “Margaritaville” was finished in a traffic jam. Stuck on the Seven Mile Bridge after a wreck, heading back from a gig, Jimmy wrote the final verse right there in his car.
Go fast enough to get there, but slow enough to see. That day on the bridge, going nowhere fast, he saw everything he needed.
“Wastin’ away again in Margaritaville.”
— Margaritaville
Later that evening, he debuted “Margaritaville” at Crazy Ophelia’s, now Antonia’s Restaurant, forever intertwining the song’s legacy with the free-spirited essence of Key West.
The story in his own words: “…I was on the Seven-Mile Bridge, and, ah, somebody had
broken down on the Seven-Mile Bridge. And we were stuck there for an hour, and I just sat out there on the Seven Mile Bridge, just looking out, and I finished the song there, and I got to Key West. And I was working in a little club on Duval Street called Crazy Ophelia’s, and I went in, and I had to work that night, and I played the song. People liked it. I went, ‘Wow, this is pretty good.’ And, you know, it was, it was fresh. It was probably six hours old. Maybe even four years before it got recorded.”
Caroline Street: Where the Island Sings
“Woman Goin’ Crazy on Caroline Street” plants a flag on an actual Old Town corridor where doors stay open, music spills onto sidewalks, and conversation becomes percussion. Today, Caroline Street still hums with that edge-of-chaos energy Buffett sang about.
“There’s a woman goin’ crazy on Caroline Street.”
— Woman Goin’ Crazy on Caroline Street
Also on Caroline Street by the Seaport is B.O.’s Fish Wagon, a funky little shack that was always a hangout for the Coral Reefer Band. With its mismatched chairs and license plates on the walls, this ramshackle spot served grouper sandwiches and cold beers to musicians, shrimpers, and locals alike. B.O. himself was part of the local color that made Key West special.
Still there today, still serving killer grouper sandwiches, it feels like a time capsule of old Key West.
Living Next to Louie’s Backyard
In the 1970s, Jimmy Buffett lived at 704 Waddell Avenue—right next door to Louie’s Backyard—where the sea breeze and sudden squalls set the daily rhythm. Those Waddell years shaped the island-life themes heard on his mid-’70s records, including Living and Dying in 3/4 Time (1974) and A1A (1974), with songs like “Trying to Reason with Hurricane Season” capturing hammocks, Bloody Marys, and weather rolling in as hurricane season brewed.
“But there’s a tropical depression brewing this week.”
— Trying to Reason with Hurricane Season
Louie’s Backyard and the Afterdeck Bar are just a five-minute walk from Southernmost Beach Resort, where you can still reason with your own hurricane season.
Blue Heaven: Morning Rituals
At the corner of Petronia and Thomas in Bahama Village, Blue Heaven earned its own Jimmy Buffett song title: “Blue Heaven Rendezvous.” Roosters wander the open-air courtyard, banyan branches cast easy shade, and late morning has a way of lingering. At the time, many would stumble upon it on a slow walk into Old Town and fall into the same unhurried rhythm he celebrated. No rush on the table. Roosters set the pace. Morning lasts as long as it needs to. Today, Blue Heaven is one of Key West’s most popular restaurants, capturing the island vibe and spirit that Jimmy lived.
“Those crazy days and crazy ways
We never want to un-do
We’ll be together now and forever
At the blue heaven rendezvous
We’ll be together now and forever
At the blue blue heaven rendezvous”
— Blue Heaven Rendezvous
Fausto’s: Morning-After Reality in Key West
Buffett’s Key West wasn’t just beaches and bars—it ran on routines and touchstones, and Fausto’s was one of them. He even name-checks it in “My Head Hurts, My Feet Stink, and I Don’t Love Jesus,” snapping the scene from hazy dawn to island daylight:
“I’m goin’ down to Fausto’s, get some chocolate milk
Can’t spend my life in yer sheets of silk
I’ve got to find my way
Crawl out and greet the day”
— My Head Hurts, My Feet Stink, and I Don’t Love Jesus
The lines ground the hangover humor in real Key West geography, reminding that between nights at Louie’s and storms rolling in, there were early-morning errands and a local grocery woven into daily life. Fausto’s on Fleming is still there today.
Shrimp Boat Sound:
Nestled in the Key West Historic Seaport, between Schooner Wharf Bar and Conch Republic, a former shrimp ice house became Jimmy Buffett’s studio in 1986. He cut Hot Water here in 1987, returned for Barometer Soup, and shared the room with friends over the years. Today, the studio
is still active and layered in stickers like a well-traveled guitar case, humming with the stories Jimmy left behind. (Read more about Shrimp Boat Sound and Hidden Stories and Iconic Locations You Didn’t Know About.)
The First Margaritaville
Margaritaville began in 1984 as a small, funky gift shop at Lands End Village across from the Half Shell Raw Bar. “Let’s call it Margaritaville, print the song lyrics on t-shirts, and see what happens,” Jimmy said when opening the shop. Within about two years, it expanded into food and drink and ultimately settled at 500 Duval Street in the old Kress Building, where the Key West location remains today.
“If life gives you limes, make margaritas.”
Read the full story at Our Key West: Remember When Margaritaville Was a Mom & Pop Shop?
The Celebration Lives On with Just A Few Friends
After Jimmy Buffett passed in September 2023, Key West did what it does best: the island came together to honor and celebrate Key West’s favorite son. On Labor Day Weekend, Key West now celebrates Jimmy with Just A Few Friends, a four-day celebration of music, stories, tours, parties and that particular Key West magic Jimmy captured here in paradise.
What started as a grassroots tribute is becoming tradition, the kind Jimmy would appreciate: organic, heartfelt, and just a little bit loose around the edges.
“Some of it’s magic, some of it’s tragic, but I had a good life all the way.”
— He Went to Paris
That line might have been about a character in a song, but it captured his own story, too. The magic was Key West. The tragic was having to leave. The good life was knowing you could always come back.
“If there’s a heaven for me, I’m sure it has a beach attached to it.”
These aren’t just stories about Jimmy Buffett; they’re places anyone can step into. Bring a little time, a little curiosity, and let the island echo his tunes. His spirit lives on. #somolife