August 31, 2024

Do you know what you were doing on the morning of September 2, 2023? We were in our kitchen doing our standard stuff, eating breakfast and opening up our phones to see what happened the night before. It was me. I was the one that first saw the shocking news. I took a big gulp and said to Ed, Jimmy Buffett died. Those 3 little words changed the course of our day, week and possibly the last year.

Here we are a year later and we made the 8 hour trek to Key West to be part of the 1^st annual Jimmy memorial weekend. In our plans for the weekend, aside from scheduled activities by the Friend of Key West group, we decided to take a journey in Jimmy’s flip flops. Below are our adventures and what we believe Jimmy would do on a trip to one of his loved Particular Harbors.

Jimmy had a long history with Key West, having arrived in November 1971 for the first time. How do you decide which old haunts he would revisit? We think he would reminisce at the spot where he played his 1st gig, then ride down the block to where he played sets regularly, and round out his reminiscing at the spot where he met his wife.

Crazy Ophelia’s was where our WWJBD tour kicked off. Even though the place is gone, the building still stands and now it’s home to Antonia’s restaurant. We peeked inside and tried to picture how it was back in the 70s, and where Jimmy might have set up his stuff. Antonia’s has such an inviting vibe, we ended up booking dinner for our last night of the trip!

On to the Snake Pit, or what was once the Snake Pit. We peddled down to 208 Duval, to visit the spot where ladies dance for dollars. Stories have been told about all of the debauchery of the 70’s. I guess the building was destined to be an adult playground, as it’s now the Red Garter Saloon. In all of our trips to Key West, we never knew there was a historical marker…….

Our last haunt was the Chart Room. It’s a little hidden, a little quirky, well, it’s just little. It’s located in the upscale Pier House Resort. The barroom used to be a hotel room and was converted back in 1967 to the same bar you see today. Not much seems to have changed since then, except for the phone booth outside where Jimmy met his wife. Sadly, that’s gone now. I might just have to start a petition to get it back, you know, for a cool Instagram photo op. There are also rumors that this was the first bar Jimmy hit up when he got to Key West in 1971.

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Our next adventure in our WWJBD day is lunch. Jimmy used to live next door to Louie’s, so that’s where we headed. He was a regular patron and had his favorite table. Louie’s Backyard is rumored to be the bar next door that Jimmy stumbled to in Trying to Reason with Hurricane Season. We noshed on conch fritters, Caesar salad and some not-so-ordinary steak tacos. I washed all that down with Louie’s Champagne Cooler. YUM!

Back on our bikes, we rode down to the other end of the island and hit up the Historic Seaport. We found a bench, sat back and watched the captains navigate the harbor on their way back in from a day of fishing. Unfortunately, at this point, Jimmy’s boat has been sold and no longer in the harbor. That didn’t stop us from imagining what it would have been like to randomly run into Jimmy in his Bermudas and flip flops coming in from a day on the water.

With ShrimpBoat Sound nestled right in the harbor, it’s easy to imagine Jimmy popping by after a quick check on his yacht. We picture him grabbing his guitar and strumming a spontaneous tune about his day. For years, we’ve made the pilgrimage to this little white, unassuming building, and today’s visit is a bit more reflective. While we feel the weight of losing a legend, we’re reminded that this spot has gifted us countless Songs You Know By Heart, instantly transporting us back to our laid-back, carefree afternoon.

Last and certainly not least, on our WWJBD day, we know Bubba would have made his way to a bar, grabbed a drink and listened to some local music. It’s well documented that Jimmy was close friends with Captain Tony and spent many a night raising a ruckus at the now-famous Captain Tony’s Saloon. So, that’s where we’ll wrap up our day – raising a glass in true Buffett style.

When you’re at Captain Tony’s, there are a few essential activities you just can’t skip. First up, grab a quarter and aim for the grouper’s mouth. No cheating—you have to face the street and launch the quarter backward over your shoulder. Next, hunt down Jimmy’s barstool. Here’s a tip: it’s retired and hanging out in the pool table room. Finally, take a daring trip to the men’s bathroom to find the hand-written lyrics to “Last Mango in Paris,” penned right there in honor of Captain Tony.

Did we leave anything out of our WWJBD Day? Drop a comment and let us know!