Jimmy Buffett’s new Tampa cruise and the question of legacy

I feel most insignificant gazing up at the stars or pondering what happens inside a supermassive black hole. Or, you know, reading how Harvard researchers recently said aliens could be on Earth passing as humans, which, correct me if I’m wrong, is the plot of “Men in Black.”

Other times, a Jimmy Buffett cruise does the philosophical trick.

Haven’t you heard? A new Margaritaville at Sea cruise just launched from Port Tampa Bay with trips to Mexico and Key West. The vessel is an ode to the musician who died in 2023 at 76. In his life, Buffett became a marketing behemoth on behalf of Total Relaxation, a spokesperson for the delusion of leaving one’s problems in the snowy driveway, embodying the son of a son of a sailor and getting schnockered on sugary margs.

Per our reporter, the ship’s soaring premises house a large teal flip-flop, margarita chandeliers, floating fish, flying parrots and a replica of Buffett’s personal seaplane. A message on the side of the vessel declares the time always five o’clock. There’s a Port of Indecision buffet, a Fins Up fitness center, a Cheeseburger in Paradise burger bar and endless opportunities to tune out life in pursuit of pickleball and vacation meats.

Buffett’s empire, which grew to include restaurants, stores, vacation clubs, marijuana and more, represents a fantasy; anyone from Florida knows that falling asleep face-down on the sand is a dermatology invoice waiting to happen. And while it’s tempting to punch down at Parrotheads for partaking, the reality is that this cruise sounds … fun. Whatever Buffett was like in private, he built a massive, colorful persona that will long outlive him.

Here’s the sunscreen rub: The deaths of our icons makes us take stock of our own smaller lives. What I mean is, we’re all going to die someday — this is going great, pour a rum runner! — and we better have our proverbial cruise ships in order. When the living think back on us, a set of imagery will spring to mind. The iconography of our life. The dressings of our memory. The salt on our rim.

In the spirit of the man who esoterically wrote “My Head Hurts, My Feet Stink, and I Don’t Love Jesus,” let’s play a game. If someone were to fashion a cruise ship experience around your personal universe, how would that materialize? Email me, I beg you, and I’ll publish the best answers in my next newsletter.

I’ll go first. My cruise ship would be littered with Diet Coke cans that have two warm gulps left in the bottom. There would be a laundry facility, but the laundry would never get done. For entertainment, we’re talking gallons of cold sauvignon blanc and a portable karaoke machine with one busted microphone and the complete catalog of Destiny’s Child. Four half-read novels would litter every table, not a single coaster in use.

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As a Gemini, my cruise would party hard for three to five days, which does not sound all that different from the Margaritaville cruise. However, after getting a mysterious aura behind the eye, the ship would need to dock back at the home port and go dark. When potential new customers try to book a trip, my customer service bot would reply a week later with, “Sorry, just seeing this.”

My cruise would be an acquired taste, as would yours, as is Margaritaville at Sea. But, hey, in these times rife with internet judgment, high interest rates and societal pressure to never be cringe, it might be exciting for us all to become a little more acquired. Who wants their legacy to be “large format beige tile that will aid in resale”? What cruise ship can be decorated with sensible slacks and sound financial decisions?

Go off, Margaritaville at Sea! Blast “Why Don’t We Get Drunk,” a song that made my parents feverishly attempt to fast-forward the tape deck every time. Serve ersatz Huli Huli chicken and yoga mimosas. Deploy the character actor in the plushy parrot suit. Cascade forth from Tampa Bay as a gaudy, confident reminder to steer our freakish ships, however uneven they may sail.

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