There are plenty of Jimmy Buffett fans in Caroline County. I sat with some in the North Caroline High School band room as us students attempted to learn “Grapefruit Juicy-Fruit” on the guitar. I have attended myriad concerts of his with locals and bumped in to others tailgating at venues like Merriweather Post Pavilion and Jiffy Lube Live, not to mention enjoying quality area acts such as Chris Sacks that cover his music. These “Parrotheads” as Jimmy Buffett fans are known can be easily identified by their attire on concert day — grass hula skirts and coconut bikini tops for example — and those are just the men!

In all seriousness, or about as serious as trop rock enthusiasts are willing to be, Jimmy Buffett’s “gulf and western” genre continues to be successful both artistically and commercially because it provides escapism from the real world. Pop in any random album of his and each song takes listeners away to a different time and place where existence is bliss — full of sunshine, clear water, and often copious amounts of adult beverages. Buffett sells happy hedonism, you might say.

Readers may be scratching their heads and wondering at this point: “Jimmy Buffett? Margaritaville? One hit wonder! He’s still around?” I know that was my father’s reaction when he saw me decked out in my tropical threads leaving the farmhouse for my first Buffett show in 1997. News flash: it’s 2023. Buffett might be most well-known in the mainstream for his signature song about a lost shaker of salt, but to those that live the lifestyle, the adoration is obvious as every concert he gives is a three hour sing-a-long of fan favorites from his more than 60 albums. Attendees know all the words and even dances that go with each song.

Buffett has not stopped with live shows. Perhaps you have dined at a Cheeseburger in Paradise, Margaritaville Cafe, or the LandShark Bar and Grill in Baltimore. Maybe you’ve picked up some Buffett-branded shrimp, beer, tequila, or flip-flops at a nearby store. Possibly you’ve gambled at a Margaritaville Casino or stayed at a Margaritaville Resort, one of which is currently under construction in Ocean City. If Jimmy Buffett is a one-hit wonder, then he has to be the most successful ever; at press time his net worth is approximately $550 million. Not bad for a fellow history major.

How does he use his money? To practice what he preaches, of course. Buffett is invested in the Miami Dolphins, has owned interest in several minor league baseball teams, has been seen at courtside of Miami Heat games, flies his own private plane, and has even been spotted sailing the Chesapeake Bay (the 2009 song “Beautiful Swimmers” is about Eastern Shore crabs, by the way).

That is, of course, when he isn’t working appearing in movies like The Beach Bum alongside of Matthew McConaughey and Snoop Dogg or working on a Broadway play based on his music or churning out yet another best-selling book; Buffett is one of few writers who has attained #1 on the New York Times fiction and non-fiction lists. Ernest Hemingway is another such author, and clearly a kindred spirit.

I don’t want to elbow myself into that elite company, but I understand the mindset. I have been independent with a desire to live a carefree life as long as I can remember. To put it pithily, I want to do everything ever — and not necessarily for the accomplishment but rather to stand in the moment of the past and present. Previous Caroline Review articles have explored my attempt to check off every national park, walk across the country, see every county, visit every NASCAR track, and more. That OCD-fueled way of thinking eventually overlapped with my love of and knowledge of Jimmy Buffett songs.
It is crystal clear to me where this one of many travel quests began. It was 1994 and I had just received my driver’s license. There was a radio show called Country Gold Saturday Night that played all the hits that modern stations did not. I would be driving home along the Denton-Greensboro Road and more often than not the deejay would play a Buffett tune. His musical arrangements and his lyrics stuck out as unique; I was intrigued. So for my next birthday I asked for a Buffett tape and was given Songs You Know By Heart. As a tongue in cheek nod to his “Margaritaville” standard, next to the title the words in the parentheses note that the subtitle of the album is his ‘Greatest Hit.’ Not a typo!

I could not get enough, so for Christmas I requested his boxed set known as Boats, Beaches, Bars, and Ballads. I listened to those songs over and over and over again, often becoming annoyed about why they were never played on the radio. But instead of going on the attack, I knew that going to a concert was next. I have been to more than a few, and enjoyed myself immensely.

Readers might have expected the concert experience to be the climax of this article. It’s not. Just like seeing Alaska, words and even pictures cannot do a Buffett show justice. You have to experience one firsthand to appreciate it and then a bunch more to completely make sure the hypothesis about a guaranteed good time is adequately supported.

Instead, I am taking you in your mind to me sitting at a red light in Anne Arundel County listening to, of all things, “Highway Don’t Care” by Tim McGraw and Taylor Swift. While I am a fan of neither, I let the song play as some undefined emotion frothed in my chest. Was it anger? Maybe. I was at least offended, not on the level of Karening, but I remember thinking to myself as I considered requesting to speak to the manager of the radio station, that in my experience, “THE HIGHWAY DOES IN FACT CARE.” The longest sustained euphoric seasons of my life, either alone or with a rotation of people and pets who have come and gone from my side, were during the planning and execution of road trips. So it just popped into my head randomly, on November 28th, 2012, that I had to see every place mentioned in every Buffett song. Good things happen in Glen Burnie after all.

In an incredibly awful year for me personally and professionally, I suddenly roared back to life with purpose. Have I visited every single lyrical reference since I first made the decision to Buffettize my travel a decade ago? Not even close. Is it something that has brought meaning, purpose, and joy to my life? Yes indeed.

For example:

Key West, Florida, is Jimmy Buffett Ground Zero. Though his first stint there lasted for just seven years, it defined him for about the next fifty. My first visit was in 2009. I sought out a “Jimmy Buffett Reality Tour” guide and got to see everything from where he originally lived to where his subtly placed Shrimpboat Sound recording studio is hidden in plain sight. There are so many Key West bars and restaurants and stores that use his lyrics for their business names there I can’t possibly list them all, but I will say that the walking tour started at Captain Tony’s Saloon, which is the focus of the song “Last Mango in Paris.” I made sure I steered clear of women going crazy on Caroline Street, as well. I did, however, serendipitously bump into Jimmy’s harmonica player, Fingers Taylor, who just happened to be hanging out with the crowd at Hog’s Breath Saloon.

Fewer people know that Jimmy and several Buffett family members have long been entrenched in Montana. So I had to go and experience a Livingston Saturday Night, on a Monday there I swore there would be no room for doubt, and true to prophecy, experienced a blow-up In Missoula. To ease my stress from the aforementioned quarrel that may or may not have taken place in a Holiday Inn full of surgeons, I undoubtedly scheduled some down time relaxing and recharging at Chico Hot Springs. To be fair, that last reference is not part of a song but instead from a 1975 film starring Jeff Bridges and Sam Waterston called Rancho Deluxe featuring an extended bar scene cameo from Jimmy himself.

Buffett music is very popular along the Gulf of Mexico, since that is where Jimmy was born (Mississippi) and raised (Alabama). I went to Galveston not for Glen Campbell but to re-enact “Who’s the Blonde Stranger?” line by line. In New Orleans I ate donuts at the Cafe du Monde that were too hot to touch and yet, just like a fool, I ate until I ate way too much. I have found myself watching the sun going down around Biloxi, taking in moonbeams on the bay in Mobile, and have completed The Pascagoula Run. I might have even passed through the town where Buffett’s sister Lulu owns a bar, bought the house a round, and signed my name on the wall of a ladies bathroom stall. It’s my job to be a shining example of love in decline, after all.

I could go on all night entertaining fellow Parrotheads working in obscure lyrics that are a long way from West Nashville ballrooms, but I only have so many pages to fill per issue so I can assure you that the coast is clear. I will close by quoting a few lines from “That’s What Living is To Me” (a song I incorporate into motivational speeches when organizations schedule me) and hope that this column encourages you to follow your own songlines wherever they take you and with whoever escorts you on that whimsical musical journey:

Be good, and you will be lonesome.
Be lonesome and you will be free.
Live a lie and you will live to regret it.
That’s what living is to me.
That’s what living is to me.