Are There Any Pirates Left in Key West, Florida?

Are there any pirates left in Key West? Any vestige of the old days of intrepid adventurers, colorful locals, and crusty hangouts? "Yes", "Yes", and "Define 'crusty'".


Key West, Florida has a long-established and sort of romantic reputation as the end of the line in the US of A for those seeking escape, or refuge, from the mainstream.  It's closer to Cuba (ninety miles in fact) than most of it's own state of Florida. The "first and last stop on A1A" has always been the renegade child of the family left to its own devices - or vices - to play with the wrong crowd of pirates, bootleggers, salvagers, entrepreneurs and revolutionaries. Along the way, the offbeat island atmosphere attracted its share of artists, writers, and square pegs who found its laid back charms a better fit for the life they were seeking. 


George has been performing on the streets of Key West for nearly 20 years, his trusty, furry companion King Coconut by his side. 

MEET "King Coconut"

KC is relatively new to this, having been on the scene with his owner Cowboy George for just a few years. But he's a quick study. His costume here was more of a Biker/Pirate look, though he has others including a Bumble Bee costume.

"He's a true professional" George told me! 

My first of many trips to Key West was over 25 years ago, and at the time I remember thinking how charming it probably was 50 years before - precarious enough to be interesting. And still "crusty" - both the people and atmosphere a little tarnished, contrasting the rest of Florida's manicure. 


You know how it is when you discover those out-of-the-way places, still loaded with charm, where everyone has an untold story? You don't realize at the time that you should enjoy it with everything you've got because 20 years from now, a lot of the charm may be gone. Hindsight being what it is, "Boy, it's really gone downhill" or "That place'll never be the same" roll off our tongues as easily as "Kids these days...".  Well, let's admit it, nothing is like it used to be, everything changes. (And news flash - kids are exactly the way they used to be, if we remember ourselves correctly without the good old selective memory of ours!) 


So when my sister suggested a trip to Key West since she and my niece had never been there before, I thought "Hmm, Key West virgins....could be fun! Or...maybe not." I had a feeling they might like some of the more recent, more commercialized and mass-produced aspects of Key West I'd seen in my recent trips. Not so bad for first timers.


Jeep is the second oldest street performer in Key West, performing and playing the banjo for over 30 years!  He's obviously doing something right judging from his day's pay. Lest you think street performers in Key West don't pay taxes, think again. 

Me: "What's still crusty about Key West?

Jeep: "Me. Sorry, I didn't get a shower this morning."

I, on the other hand, wanted to see if Key West still had what I always loved about it - more grit and less polish. I wasn't a newbie. I wanted to find the 'pirates' and I'm not talking about the ones around town dressed up like swashbuckling Jack Sparrows. But rather the colorful and unique characters that have long made Key West what it is, living life on their terms, flipping a bird to the world and saying 'thanks for the pleasure but I'm doing it my way'. I admire the crap out of that, because I'm not sure I could do it their way. I applaud their "live and let live" philosophy, their desire not long ago to secede from the union and make the Conch Republic it's own country, and their entrepreneurial spirit. They have my vote, those Pirates of Key West - young, old, gay, straight, Haves and Have Nots, and everyone in between. They bring more color to an already blended palate in Cayo Hueso.


But between my recent visits the past several years and what I'd heard and read about the commercialization of Key West, I was honestly hesitant about going at all.


As it turns out, I was right.


The first-timers to Key West loved it. As Key West virgins, they were swept up in the same energy and carnival fun I'd felt the first time I strolled down Duval Street to Mallory Square. What they didn't care for so much was my insistence at looking for the 'crusty', even calling it 'crusty' for that matter. "Aunt Lori, that's just gross. Call it something else." How I wished I could explain it to them so their virgin ears and minds would understand! They would someday, they just had to fall in love with it first, and no doubt they did.


I was right, but I was also wrong. 

MEET B.O. aka Buddy Owens, owner of the famous B.O.'s Fishwagon

What a thrill it was to pull up and meet B.O. at the Fishwagon. I'd seen his likeness over the years, in pictures and on the side of the truck door out front. And he couldn't have been nicer - shook my hand and let me snap a quick picture. A legend in Key West, this man has made the best fish sandwiches on the island for over 50 years!

 The iconic B.O.'s Fishwagon in Old Town near the Bight

The iconic B.O.'s Fishwagon in Old Town near the Bight

Despite the obvious growth in tourism and a more family-friendly feel (at least in the lower blocks of Duval Street), the pirates and crusty local hangouts are still there, though perhaps a bit mellowed with age or experience! Yes, they're still there - the free spirits, rebels, poets, and dreamers are still hanging on and hanging out. You'll find them all around town, performing for crowds at Mallory Square or behind the counter at their restaurant. And not all of them are 'winding down' with age. Although some Milennials may not be too familiar with Hemingway's work or his mystique, I met more than a few who showed me their love of Key West and an impressive commitment to something more inspiring - conservation and protection of the delicate reef and ecosystem here - one of Key West's greatest assets.


Jimmy Buffett wrote many a songline in and about Key West, but one line in particular couldn't be more true. In 'Blue Heaven Rendevous', he sang of the funky restaurant here named Blue Heaven, and answered the very question I wondered myself.  "There's still some magic left in this tourist town."  


Without a doubt, there is magic left. And every reason to hope for the future.



Have you been to Key West over the years? Who am I missing, and who would you add to this list of our favorite "pirates"??