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Exile on Duval Street

  • Writer: Tom Piper
    Tom Piper
  • 4 hours ago
  • 4 min read

Your tireless leisure & travel correspondents, Tom & Lori, remain committed to travelling to hell and back so that you don't have to. Speaking of why no one should travel, did you see the latest Cruise News? Hantavirus... As if the backed up toilets weren't enough.


At any rate, we are back in the Conch Republic. Here we go again, again. We seem to have a condition known as Keys Disease. It's a real disease, with doctors and everything.

(there are two movie quotes in that paragraph. A free subscription to this free blog for those who can shout out both).


The Proud Republic
The Proud Republic

People often ask "what's your deal with Key West?" Lori usually begins with something about the lovely weather and the exquisite architecture of the homes (Zzzzz...) I then loudly interrupt with: "Did you know that there are over 300 bars on an island about the size of a Jeff Bezos yacht?"


There are over 40 bars on the one-mile stretch of Duval Street alone, including the world's smallest bar. But it's not just the drinking. There is so much more to this town. For example: there is... ummm, well there is lots of other stuff. I think there are probably some museums. I'm pretty sure there is a train (on wheels) that you can ride. The rest you can look up on the internet. I can't do all the work here.


Choo Choo
Choo Choo

There are certainly lots of boats. I only know this because my wife always insists that we go out on several of them while we're here, to which I readily agree because a) I'm a little afraid of her, and b) the boats have bars on them.


Here she is on our Tiki Boat Charter
Here she is on our Tiki Boat Charter

Another thing my wife insists on doing when we're absolutely anywhere is to go to the local farmers market. And, sure enough, even they have a bar. Not a single farmers market I have ever been to in Vermont (and that's a few hundred at last count) has a bar. So you just have to respect the commitment down here.


I love Farmers Markets! I never made it to the crafts and produce area.
I love Farmers Markets! I never made it to the crafts and produce area.

Something else you see a lot of in Key West is Parrot Heads. Parrot Heads are those people who are members of the Jimmy Buffet tribal group. To join, you have to like Jimmy's music (not just the hits), and be willing to wear some pretty embarrassing clothes and hats. While Jimmy was still alive, Parrot Heads went to his concerts, wearing their funny clothes. But now they still come to Key West to pay their respects to their fallen demi-god.


Parrot Heads
Parrot Heads

And there are plenty of ways to do so.


For example, you can stay at the Key West Margaritaville Beach House, one of the many Buffet-themed hotels around the world. You can ride your fixed gear down to Duval, stopping to buy a Jimmy tchotchke at the Margaritaville gift emporium, before enjoying a meal and signature drink at the Margaritaville Cafe. If you prefer to arrive in style (like the son of a son of a sailor), feel free to board any of the Margaritaville Cruise Ships that make port in Key West each week. Or, if you're on a budget, just grab a Landshark Lager, also owned by the Buffet brand empire.



Jimmy made a nice little living selling records and tickets. A few million bucks to be sure. But he made a billion dollars (that's one-thousand million, give or take) by licensing his lifestyle brand to companies that sell stuff to people who like to wear funny hats and shirts.


Hang Fire


How did he do this? Jimmy single-handedly popularized the nobility of the tropical slacker. There have always been tropical slackers, but before Margaritaville, we tended to refer to them using the more politically correct term of "bums."


Back then, you might admit for example, with no small degree of family shame, that:


"yeah... my cousin Nick, he crews on charter boats somewhere down in the Keys, I think he is drunk most of the time... It's a little bit sad"


Then Jimmy wrote his song and we all realized that the bums were actually philosopher kings. Now you say:


"Yeah! my cousin Nick, he crews on charter boats somewhere down in the Keys! And I think he is drunk most of the time. Dude is a fucking legend!"

For more on the Buffet Slacker Empire, you can read about the in-depth/slacker research that Ramble On did about the Margaritaville 55+ Communities where you can pretend-live the Tropical Slacker Lifestyle every single day while collecting social security. Though you will still have to play Pickleball, which is just one of the unfortunate, but unavoidable, requirements of these places. I don't know if you can wear the silly clothes during that or not.


There is some possible irony to the fact that while we the people, inspired by Mr. Buffet's songs, were chasing dreams of a simpler, saltier life, away from the soul destroying careers that we had unintentionally stumbled into—Jimmy was busy printing enough money to buy a mid-sized Caribbean country. But I don't judge.


All I know is that when I'm in the Keys, the livin' is easy. As long as I have a fistful of credit cards.



My (current) favorite spots in Key West:


  • Salute! - Always a lovely day at Salute! Try the caprese salad w/avocado. We saw Jimmy B's sister here this time. Celebrity adjacent siting.

  • General Horseplay - Best bespoke cocktails in Margaritaville

  • First Flight - The brisket mac n' cheese is still haunting my dreams

  • The Alamo - good bands and a terrific Philly Cheesesteak slider

  • Breakfast at Blue Heaven, The Moondog, and the Banana Cafe

  • The Green Parrot - When Lori finally wises up and leaves me, and no one has heard from me for over a year or two, look for me here. I'll be at the bar.


Alas, vacation is over. It's back to the travel grind. Ireland is next.



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Tom Piper hard at work on travel planning

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Hi. I'm Tom and Lori is my travel partner and better half.

We love to travel. Ramble On is your resource to learn how to avoid doing all the dumb things we do and only do the especially wonderful things.

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