Key West: Jimmy Buffett Walking Tour & Pie Tasting

Summary

Jimmy Buffett’s Key West music walk pie tasting & old bars

You’ll wander Old Key West with a local guide tracing Jimmy Buffett’s early days—see bars where he played his first gigs, snack on tangy Key Lime Pie, and finish with a drink at Capt. Tony’s Saloon. Expect stories you won’t find online and little moments that stick with you long after you leave.

What’s the experience like?

The first thing I noticed was the neon green shirt—our guide waving at us outside Margaritaville like he’d just stepped out of one of those old album covers. The air smelled faintly like salt and sunscreen, and there was Jimmy’s music drifting from somewhere, not too loud. We were a small group, mostly fans but also a couple who just liked the idea of wandering Old Key West on foot. Our guide (I think his name was Mike?) started off with this story about Buffett’s first gig here—he pointed to a bar that looked like it hadn’t changed since the 70s. I tried to picture it: sticky floors, cheap beer, everyone sweating through their shirts. Maybe that hasn’t changed either.

We ducked into a few places—some were half-empty even though it was early afternoon. There was one spot where Mike said Buffett used to scribble lyrics on napkins. I touched the worn wood of the bar and wondered how many other hands had done the same thing. At one point we passed a guy strumming an old guitar on the sidewalk; he nodded at us but didn’t stop playing. The sky kept shifting between blue and cloudy, which felt right for this kind of wandering tour.

I’ve had Key Lime Pie before but never like this—tangy and cold, with that weird graham cracker crust that kind of sticks to your teeth (in a good way). We ate standing up outside, laughing about whose slice was bigger. Someone tried to remember all the words to “Margaritaville” and failed spectacularly. Then we walked past Mallory Square where you could smell fried shrimp from somewhere nearby—my stomach rumbled even though we’d just eaten pie.

The last stop was Capt. Tony’s Saloon. It’s dark inside, walls covered in stuff people left behind—license plates, bras (not kidding), faded Polaroids. Mike handed us each a drink (included in the tour) and told us one last story about Buffett recording late at night here when nobody else wanted to play. I sat for a minute just listening to the chatter around me and thinking about how some places really do hang onto their ghosts. Not sure what I expected from a Jimmy Buffett tour in Key West, but now every time I hear “Cheeseburger in Paradise,” I can almost taste that pie again.

Step-by-step itinerary

Day 1 — Jimmy Buffett walking tour in Key West

• Meet guide at Margaritaville
• Visit locations inspiring Buffett's songs
• See where he played first gig
• Stop at favorite watering holes
• Visit places he ate and bars
• Tour his recording studio
• Eat slice of best Key Lime Pie
• Visit first Margaritaville location
• Explore Mallory Square
• End at Capt. Tony's Saloon
• Enjoy souvenir alcoholic beverage

Top questions

How long is the Jimmy Buffett walking tour in Key West?

The guided walking tour lasts approximately 1 hour and 30 minutes.

Where does the Jimmy Buffett tour start?

The tour begins outside Margaritaville in Old Key West.

Is food included during the tour?

Yes, you get a slice of Key Lime Pie as part of the experience.

Do you visit any bars or saloons during the tour?

Yes, you visit several historic bars including Capt. Tony’s Saloon.

Are alcoholic drinks included?

You receive a souvenir alcoholic beverage at Capt. Tony’s Saloon.

Is this tour suitable for travelers with limited mobility?

The tour requires at least moderate physical fitness; not recommended for those with poor cardiovascular health.

Can service animals join the tour?

Yes, service animals are allowed on this walking tour.

Does the Jimmy Buffett walking tour include Mallory Square?

Yes, Mallory Square is one of the stops along the route.

What’s included

Your day includes meeting your guide at Margaritaville for a walking tour through Old Key West with stops at historic locations tied to Jimmy Buffett’s life and music; you’ll enjoy water along the way plus a slice of real Key Lime Pie before ending at Capt. Tony’s Saloon with an included alcoholic beverage.