Road Trips with Jason Crane: The Florida Keys

I crossed something off my bucket list this week by finally visiting the Florida Keys. I’ve always wanted to go there, ever since I first heard about them on the radio show Bold Venture, which starred Humphrey Bogart and Lauren Bacall. I made it there a couple days ago as part of my van life journey. I did all the things you’re supposed to do: took a selfie at the Southermost Point Buoy, looked at Hemmingway’s house, and took a walk around Old Town, to name a few. I also found out through a friend that jazz trumpeter Fats Navarro was born in Key West, so I went to see his childhood home.

Of course you can’t set foot in the Keys without thinking of music. For me it’s three songs in particular. Let’s get the biggie out of the way first.

“Margaritaville” by Jimmy Buffett

Perhaps no artist is more associated with that Key West feeling than Jimmy Buffett. He started writing his most famous song in Texas (inspired by a drink he had a bar in Austin) and finished it while in Key West. Just in case you’re thinking the whole Buffett/Key West connection is overblown: Yesterday I was parked on a side street in Key West with the windows down. A guy came out on his porch, cracked open a beer, and started blasting Jimmy Buffett. So it’s real. It’s very, very real.

I was on the phone with my sister as I entered the Keys, and mentioned “that famous song.” But my sister and I had two different songs in mind. The one I meant was this:

“Key Largo” by Bertie Higgins

I couldn’t have told you who sang this song, but it’s the first non-Buffett tune that comes to mind when I think of the Keys. Of course the chorus references the classic Bogey/Bacall film Key Largo and also pulls lyrics from some of the dialogue in Casablanca. Lauren Bacall isn’t in that one, but that’s me nitpicking. Bertie Higgins is a native Floridian, although he’s from the central Gulf Coast, quite a ways from Key Largo. And the video for the song was filmed near his hometown, not in the Keys. Ah well.

My sister, as I mentioned, was thinking of a different song entirely:

“Kokomo” by the Beach Boys

I was today years old when I learned that Kokomo is not a real place, but a fictional island off the Florida Keys. The song was written by quite a team: John Phillips from the Mamas and the Papas; Scott McKenzie, writer of “San Francisco (Be Sure To Wear Some Flowers In Your Hair”); Mike Love of the Beach Boys; and Terry Melcher, who among many other things produced the first two records for the Byrds. It was featured in the movie Cocktail with Tom Cruise. It mentions both Key Largo specifically and the Florida Keys generally.

Do you have a particular song you associate with the Keys? Let me know at

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I’m writing this update next to a tiny gator-inhabited pond south of the equally tiny “town” of Palmdale, FL. I’ve been in 19 states since I left Tucson, which means I’ve been moving way too fast. The holidays necessitated a lot of that, but now I’m slowing down. Who knows where I’ll end up next?