What I learned from my hobo weekend in Key West


It’s a beautifully sunny Friday afternoon in Tampa Bay.  What to do with my weekend?  Let’s get in the car and head to Key West.  Why not?

With one extra shirt and one extra pair of panties, we head south.  We being me and my guy friend who’s free spirited tendencies are rubbing off on me.

After a couple of stops on the way at the Skyway Bridge fishing pier, Naples, and Miami Beach we arrive in Key West 12 hours later.  (It’s usually a 7 hour drive)

Beyond exhausted, we pull over and crash in the truck at a closed dentist office just off Duval St.

I’ve never slept in a car before so this is completely new to me.

My friend passes out almost immediately and I toss and turn and try to contort my body into any sort of comfortable position.  As soon as I get to sleep, it starts.

Not sure if you‘ve ever been to Key West but they have stray roosters.  And these roosters have no concept of time, AT ALL.  I can tell you I did not sleep that night.  Between the intoxicated people screaming obscenities at each other and the roosters there was no way I could pass out.

7 a.m. finally comes around.  With no sleep and no shower, we start off on our day with a breakfast beer.  After all, we’re on vacation.

Day drinking in sunny Key West.  What could be better?


This is what I learned that weekend:

  • Everyone has a story. And usually they’re pretty amazing.
  • Don’t judge a book by its cover.
  • Good company matters more than a good location (even though it was beautiful down there).
  • Waking up literally on the beach is one of the most beautiful ways to start your day.
  • If you’re tired enough you can sleep anywhere.
  • When you think you’re mad at someone, just wait an hour before reacting to see if it really matters.
  • Pepto-Bismol is wonderful.

We literally had nothing.  We walked the streets of Key West for a total of 12.5 miles that day.  I was so tired I didn’t think I could go on much longer.  Somehow we did.


Even though we scraped up gas money to get home and had a tire blow out while mid arch of the Skyway Bridge, I can honestly tell you this is one of those adventures I will never forget.

The people you meet are amazing.  From the guy sitting in a tee-pee telling people he is delivering a message of ‘love and let live’ to the gentlemen playing a broom because 3 strings on his guitar broke, these people were fascinating.  To the normal eye, they appear to be unorthodox and “weird”.  They were not.  They were more interesting to talk to rather than the rich captain who sails into the keys for the winter months.


I’m grateful to have the opportunity to run away on these adventures.  Life is meant to be lived.

Cheers to living life!

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All photos in this post were from my journey.


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