To anyone who knows me, it is no secret that I am a Parrothead.
That sentence would have surprised the younger me and occasionally still does in my middle age. I grew up liking Jimmy Buffett’s music, but I never really understood his fans. In my teens, they struck me as a little odd: the Hawaiian shirts and grass skirts, the frozen drinks, the beach balls, the endless search for Margaritaville and a missing salt shaker. The songs were fun and quirky, but I wasn’t sure I wanted to be part of the culture.
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Then came 2020.
That spring, my family was living in New York City as COVID-19 swept through the country. Ambulances screamed through our neighborhood day and night. Hospitals overflowed. Every trip outside felt unsettling, and so many people that we knew were sick and some tragically died. It was during those dark weeks that my wife and I suffered the unimaginable loss of our daughter. Like so many families, we were grieving while the world itself seemed to be unraveling.
Eventually, we packed our son into the car and drove south to Virginia, hoping warmer weather and open space might help us breathe again. Every day in Virginia, I searched for parks and playgrounds where he could run and laugh and be a little boy while the rest of the world seemed frozen.
The sun, the fresh air, the open skies and the beaches helped me beyond words. And on one afternoon, Jimmy Buffett’s version of “Southern Cross” came on the radio. The song hit me hard and totally unexpectedly; I certainly knew the song, but its lyrics about heartbreak, healing and finding spiritual clarity through a long-distance voyage took on an entirely new meaning for me.
The song uses the literal navigational star constellation of the Southern Hemisphere as a metaphor for finding inner direction and eventually peace after a painful episode in life. As the song wound down, I pulled the car over and cried.
Looking back at that moment, I realize now that “Southern Cross” was so powerful then because it spoke of heartbreak without surrender and of acknowledging loss while still believing there were better days ahead. I needed to hear that message in 2020, and with that old song, I started listening to “Radio Margaritaville” on SiriusXM. Soon, it became the soundtrack to our drives.
The songs were often delightfully ridiculous. Pirates. Beaches. Cheeseburgers. French croissants. Fishing. Escaping to islands that probably existed only in Buffett’s imagination.
The jokes were the easy part. But what kept me in the car was the perspective underneath all of them and Jimmy’s overarching messaging in his work: gratitude that sounded earned rather than assumed.
I kept listening, and then I discovered the people.
Listeners called into the station from across the country with stories of illness, loss, family, recovery and hope. They laughed and cried on the air, and they checked in on one another afterward. Before long, I found online groups full of people I had never met who somehow knew exactly what so many of us were carrying through those lonely months.
The community astonished me. They didn’t gather because they agreed about politics or shared the same careers; they gathered because they shared joy and wanted to enjoy life with family and friends.
I realized over those months that I had spent so many years thinking that Jimmy Buffett wrote songs.
What he actually built over five decades was a community — one with a standing invitation to show up, be generous, and enjoy yourself in the company of strangers who often became lifelong friends.
When the pandemic finally faded, I wanted my children to experience the world that had given so much to me. So we took our family to Key West.
My son had spent countless hours listening to Buffett in the car during those years, and in Key West the songs came alive. We wandered Duval Street, stopped for brunch at the La Te Da Hotel, saw Jimmy’s recording studio, and had to visit the famous Captain Tony’s bar.
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As we walked toward the famous saloon, my son suddenly stopped. He looked up at the awning, turned to me with a huge smile, and said, “Dad — this is Captain Tony’s!” He had connected the lyric to the place.
For years, the song had lived in our car. Suddenly it had an address and was a real place. It wasn’t just another restaurant in Key West; it was the almost sacred place where Jimmy Buffett would sing many years earlier. Watching him make that connection was one of the great joys of the trip.
By then, our family had changed. Our daughter grew up with Buffett playing in the background. She knew “Margaritaville” and she knew “Fins,” and she knew that whenever one of Buffett’s songs came on, Dad was going to sing along whether anyone wanted him to or not.
She knew I loved him; she just never knew why.
A few nights ago, after baths and bedtime routines, my daughter climbed into bed with a brand-new “Little Golden Book” about Jimmy Buffett that had just arrived in the mail.
“Daddy,” she asked, “will you sit with me while I read it?”
She is just learning to read, carefully sounding out words one syllable at a time. Every few sentences she stopped, asked me how to pronounce a word, then beamed when she got it.
She read about the little boy who explored the Gulf Coast. She read about the guitar. She read about the years spent driving from town to town before anyone knew his name. She read about the Coral Reefer Band, Margaritaville, and the man who wanted to tell stories and bring people together.
Somewhere in the middle of the book, I started becoming emotional. Not because Buffett had died; not because I was remembering a favorite musician.
As she kept reading, I wasn’t hearing Buffett’s story — I was remembering my own during those tough times. Driving through Virginia with my son, trying to outrun grief one playground at a time. The strangers who became friends over a shared love of his music. Standing in Key West, watching my son’s amazement as songs became places.
Then I looked at the little girl reading beside me. She is the daughter who never knew those dark pandemic days. She never knew the little girl we lost. She only knows that her father smiles whenever Buffett comes on the radio.
Without realizing it and without me anticipating it, she had handed me the music that carried me through grief and she did it in the voice of a little girl learning to read.
Parents spend years wondering what their children will inherit. We hope they’ll inherit our faith, our values, our love of family, our gratitude. But they also inherit quieter things: favorite books, familiar songs, places that become sacred because someone they love first loved them.
Then, every so often, something extraordinary happens. Your child hands it back to you.
My daughter finished the last page, closed the book, and smiled. She had no idea why I was crying. Someday I’ll tell her. But for now, I’m grateful that she knows the songs, that she knows the joy behind them and that she has become part of a story that began long before she could read. For years, Jimmy Buffett’s music helped carry me; a “Little Golden Book” helped my daughter carry it back.
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Fins up.