Jimmy Buffett, It’s Been a Lovely Cruise

Jimmy Buffett, It’s Been a Lovely Cruise

Jimmy Buffett Backstage Pre-Show Party, 2018

On Labor Day Weekend, 2023, Jimmy Buffett left us for a show on the other side. I’d like to think it was with his Hush Puppies on.

In so many ways, he’s been in the background of my life. Personally and professionally.

I never got to meet him. Not really. I did shake his hand from the stage once in Columbia. Randy and I were on one of our many, many trips to see him play, and we were front row center for that show. You’ve likely heard that specific show on Radio Margaritaville. It’s the one where he says, “It’s good to be back in Columbia… I’ve been reading about it. I’ve been reading about you!”

On the way to the show, we had this idea to get his autograph. We swung into Office Depot and bought a yardstick, binder clips, a Sharpie, and a sketch pad. 

Amazingly, no one questioned us as we strolled like kids who stole candy at the convenience store to our seats in the front. The concert was terrific, as usual. And I am sure I’m biased.

As the final encore wrapped up, I reached out, hoping for a brief connection. This was before the fall in Australia. And Jimmy, ever the entertainer, didn’t disappoint.  He reached down, and we shook hands. As he reached down, Randy hoisted our contraption toward him. He’d used the binder clip to clip the sketch pad and sharpie to the end of the yardstick.

Jimmy’s laughter echoed as he remarked, “I’ve never seen any shit like this before.” A brief struggle with the sharpie’s cap ensued, after which he scribbled his signature, leaving us with a piece of advice: “Next time, take the lid off before you pass it up.” And just like that, he was gone, leaving behind a memory that still brings me a smile.

Jimmy Buffett's signature from the at night in Columbia.



Jimmy Buffett inspired me in ways that are sometimes hard to articulate. He inspired a lot of the things that I consider the good life. The laid-back, slow beach living. I don’t live at a beach by the ocean, but I have a small one on a small lake here in Charlotte. I have palm trees. And an inordinate number of pairs of flip-flops. 

But he inspired my business in unseen ways. After my first show on the front row, it was clear that he was more than that tropical beach bum persona you saw.

He worked hard. And he had fun. And I realized that I could do both, too. Workin’ and playin’. He built his $1 billion empire around his music. And it’s always been clear that he loved his music, creating and performing.

I found something I love doing. Whether it’s building websites, writing, or coaching baseball. And if you genuinely find something you love, you’ll never lose your schoolboy heart.

Find something you love. Work hard at it. That’s one of the many ‘secrets’ I picked up from Jimmy over the years.

I’ll write about more of them later. But that’s not this post.

People who know me will tell you with certainty that I hold a lot of stress. I care deeply about the things I do.

But there are a few times you can physically see it leave my face. One is when i set foot in the Caribbean Islands. Another is when I got to attend a show. It transported me to that place in the Caribbean. Where, at least for me, there’s not a care in the world. 

As I get older, there are so many memories that are growing more and more fuzzy. So it’s a blessing when there’s one that remains so crystal clear.

A few years ago, Cole started listening to Jimmy when he slept. He had a CD and played the same one every night as he drifted off. He played it so often it eventually began to skip around the third song.

So, the next time Jimmy came to Charlotte, I took Cole. It was a cold, cold April. In fact, the concert had been rescheduled due to the temperature.

Cole and I had backstage pre-show party passes. We saw all of the members of the band, and we actually got to meet Peter Mayer. It was very cool.

Caroline Jones was the opening act, and she blew the roof off the place.

But then Jimmy Buffett gave us another memory that I’ll never forget. Cole wore a fantastic shark hat. The shark was chomping ferociously down on his head. Jimmy had noticed it and pointed at him earlier in the show.

Then, during ‘Fins,’ he danced right over to Cole there on the front row and bent down while strumming his guitar, and as far as we were concerned, he was singing only to him. Cole just smiled. As he stood back up to return to center stage, he stripped off one of his wristbands and gently tossed it down to Cole. I don’t know if Cole remembers it, or understands how rare a moment like that is. I wish we had it on video. But even without the video, I’ll never forget it.

That fleeting moment where Cole became the center of Jimmy’s universe is etched in my heart. The wristband Jimmy tossed to Cole after is a cherished memento of that night.

Cole and I during the Jimmy Buffett show in April, 2018.


But that was a Jimmy Buffett show. He had this way of always making the people at his shows feel special.

I have so many other memories and stories.

“I’ve been reading about it. I’ve been reading about YOU!”


I never met him. I tried. And I didn’t succeed. And that’s something I can’t often say. Even so, he inspired me in so many ways. In ways that I will never forget.

“These moments we’re left with, may you always remember, these moments are shared by few… There’s wind in our hair and there’s water in our shoes… it’s been a lovely cruise.”

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About the Caribbean Amphibians

The Caribbean Amphibians

Dive into the Caribbean’s captivating charm with us, whether you’re lounging on its pristine beaches or longing for its vibe from a distance. Inspired by the rhythms of Jimmy Buffett and the refreshing taste of mojitos, we share the essence of the Caribbean lifestyle. With a profound love for its vibrant culture and scenic beauty, we offer insights to help you embrace its magic, wherever you might be. Catering to all who dream of the Caribbean’s allure, join us in celebrating its unique spirit every day.

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