A Drinking Town with a Fishing Problem

What makes travel most rewarding for us is seeing places that still feel authentically different from anywhere else. America has been blending its “culture” together for the last hundred years. Driving down the freeway in Houston looks identical to driving in Minneapolis. The natural landscape is different of course, but the stuff people created is often indistinguishable. Once upon a time, just walking a few blocks in New York City could take you into an entirely different universe. Today, Boston, LA and Miami have more in common than not. We all flock to the exceptions for a taste of a place that still offers an authentic cultural experience. One such place can be found way at the bottom of the continent.


Lori and I were last in the Florida Keys 34 years ago. In those days, it was still scruffy and rough around the edges. Highway 1 was dotted with crab shacks and oyster joints that you could tell had been hammered together using the salvage of a shipwreck by bartenders, not carpenters. Dive motels outnumbered resorts 10 to 1. A combination of money and Hurricane Irma washed most of that funky charm out to sea. But Key West has held on to a large degree. The town is still a gem. Architectural zoning has been a big part of that. The determination of the long-time residences another.



Key West has always been a rogue town populated by rogue people. In 1982 they became exceedingly frustrated by the Government’s roadblocks set up along Highway 1 to catch drug runners as it was simultaneously choking their own tourist economy. So, they seceded from the United States, proclaiming Key West the newly minted Conch (pron: Conk) Republic. They created a flag and boldly declared war against the United States of America! Knowing that their non-existent defenses wouldn’t hold up very long, they wisely surrendered minutes later and applied for foreign aid. The town declared moral victory and got drunk. Not a lot has changed in that respect.


As referenced in an earlier post, Jimmy Buffet wrote his most famous song here (or part of it, his first actual Rita was in Austin where he started the song). In ’77 he was playing gigs around Key West, and when he wasn’t, well he was on his front porch swing, strumming his six string. Or so I want to believe. And the rest is history. According to Wikipedia, there is a lost verse that was removed from the song to make it more radio friendly. It goes like this:


Old men in tank tops,

Cruisin' the gift shops,

Checkin' out chiquitas, down by the shore

They dream about weight loss,

Wish they could be their own boss

Those three-day vacations can be such a bore


I resemble that remark.


A local will no doubt tell you that “much has changed” in Key West (which is what you will also hear in every single other town across America these days – because it has) but what has remained does still seem wonderfully, reassuringly Key West. There are loads of dive bars and non-chain restaurants. Some of Ernesto’s old haunts like Sloppy Joe’s remain along with the Green Parrot, mending broken dreams since 1890. The shops on Duvall St. are tacky souvenir shops, but thankfully not a string of national chain boutiques and Starbucks. The Hard Rock Café is there, but it’s housed in an old Key West house, not in a new, out-of-place piece of construction (the food is, however, presumably still as faithfully bad as all the other locations). And like in Jimmy’s day, there is still live music everywhere, all day and all night.


There is much more as well. A fort that played a major role in the Civil War. A museum chronicling the discovery of the Nuestra Senora de Atocha which was a Spanish treasure galleon that sunk in a hurricane off Key West in 1622. Spain looked for it for sixty years without success. It had so much treasure on board that its failure to turn up in Madrid changed the course of history. It was found by American Treasure Hunter Mel Fisher. You can learn all about it in Key West if you aren’t unavoidably detained in a bar.


Dear friends from college, Mike and Jen, were there during our visit. They have been spending a month in Key West every spring for the past 25 years. Many other friends of theirs have followed and now there is a revolving contingent of Seattle friends who are there for various parts of April and May. We had an amazing time with a few of them and benefited from their local knowledge.



We rented cruiser bikes for the week, as that is the only way to fly in Key West. The town is a grid of mostly quiet streets and ample bike lanes. We rode from bar to bar, day after day, drinking, laughing, talking, and listening to great music. Pure heaven. I wrote a song about the experience that is better than Margaritaville. But when I went to write it down the next day, I couldn’t remember it. Tribute. A missed opportunity there for sure.


Speaking of missed opportunities, we wanted to try kite boarding. I made a reservation with UpWind Kiteboarding.


The reply came from “Skot.” Now if that isn’t the perfect name for a tan, long-haired, 8-pack abs, kite-boarding instructor, then I don’t know what is? Skot probably emerged from his mother’s womb on a 29’ sloop running at 14 knots to Jamaica on a following sea. Skot was the man. He piloted us out to “The Flats” – a huge marine sanctuary sand bar protecting Key West from Gulf of Mexico storms. We waited out a few driving rainstorms that made the visibility so poor that Skot couldn’t even see the narrow channel we needed to get through. After much delay, we made it out to our destination and the sun came out. The water is only about waist deep for miles in the sanctuary, so we jumped in and began setting up our kites. Lots of knots, harnesses, clips and commands to learn. And then the wind died. We waited for about an hour for it to kick up again, but it never did. Back on shore, Skot said he would text us if it picked up in the afternoon. When that didn’t happen, he said we would try for the following day. Ironically, it had been windy every single day that we had been in Florida, until we arrived in Key West. It did not return.


So, we went disappointment drinking, which helped considerably.


If I can remember the poignant, yet catchy, song that I wrote about Key West, I will record it and get rich. Until then, just look for me at The Bull, The Smoked Tuna or The Green Parrot. I’ll be the one with a rum runner in my hand, forgotten dreams in my eyes and a zero-pack on my abs.

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