“It didn’t take me long to realize that Key West is a kooky town, full of gays, misfits, seasonal workers, drunks, trust fund kids, tourists, vagrants, and drifters, with several of those categories overlapping on a nightly basis.” Roastbeef’s Promise, David Jerome
We flew into Miami on a red-eye, arriving pie-eyed at dawn from our layover in Vegas. My travel partner was again my ol’ Disney buddy Steve, who I’d bounced around America & Europe with on other occasions. Our first thought upon arriving in the Sunshine State was where to get some sleep after a night of protecting 10-year-old Jessica, our unaccompanied row-mate, from drunk weirdos.
We caught a few zzz’s on lounge chairs at a resort pool near the airport before heading further south into the Florida Keys. The Keys are strung together by a series of bridges, like braces on crooked teenage teeth. And, like teenagers, the Keys are unpredictable, immature, and attractive to creepy older men.
With each mile maker we passed, we experienced “changes in latitude, changes in attitude” as we gazed at the Atlantic Ocean on our left and the turquoise waters of the Gulf on Mexico on our right. A sign stating, “Check your conventional thoughts,” should be posted on the last bridge at Mile Maker 0 before entering Key West, the best Key on the Key Ring.
Key West is laid back, weird, free-spirited, artistic, irreverent, and scenic. It doesn’t quite seem like you’re still in America. I had only had that experience once previously, when I visited New Orleans’ French Quarter for the first time.
We started with a Conch Train tour that showed us various buildings of interest including President Truman’s vacation home. We stopped at the southernmost point in the continental United States. The marker there looks like an astronaut’s command module purchased at a NASA garage sale, painted red, black, and yellow like a corral snake.
After all this sight-seeing, it was time for a rum runner at the world famous bar, Sloppy Joe’s. Even tea-totalers flock to this gin joint because legendary author Ernest Hemingway’s hiney used to hold down a barstool here. He’d tell fish stories, and offer sage advice such as, “Always do sober what you said you’d do drunk. That will teach you to keep your mouth shut.”
Around cocktail time (when is it not cocktail time in Key West?) we decided to leave Sloppy Joe’s and try a roof top bar down Duval Street called The Garden of Eden, which had a clothing optional policy. That always sounds great, and is also always a disappointment when you get there because all you find is some hairy, portly dude speaking in a British accent and wearing nothing but a fanny pack.
Sure enough, upon arrival there was one guy, naked as the eyes of a clown, sunning himself on a lounge chair. I don’t know if he had a British accent because we headed away from him towards the bar where we met the bikini-clad bartender named Carol.
We started in on our elbow exercises while chit-chatting with Carol, a seasonal worker from Memphis, who claimed it was her birthday, though that could have been a ploy for increasing the donations to her tip jar.
Carol had an interesting way of serving beer. Someone across the deck ordered a can of Budweiser, she reached into the cooler, didn’t open the can, but attempted to throw it overhand like Jim Everett looking for Flipper Anderson. Her aim was lousy and the can smacked off of a pole and hit me in the back. My first thought was, “I wonder if Larry H. Parker takes cases in Florida?” I ended up negotiating a shot of Jaegermeister as settlement for my injury – which is payment in-full in Key West.
“It’s tradition in Key West that everybody goes to Mallory Square at sunset,” this non-traditional, bikini-clad, tongue-pierced, off-target, possible-birthday bartender told us. So around 7:30 we headed out for Mallory Square to honor the tradition.
Upon arriving at the square, we saw about a dozen street performers: musicians, sword swallowers, tightrope walkers; all looking to make a buck off of drunken tourists. I decided that this was a good opportunity for me to show-off my very average juggling skills. I bought three whole oranges for fifty cents a piece from the guy selling fresh-squeezed orange juice. I put my baseball cap on the ground in front of me with a dollar of bait money, and started to juggle in front of the passing tourists.
Soon two kids named Jason & Casey came to my aid. “We need to get people’s attention,” I said. “Maybe you could start chanting, ‘The guy needs money, the guy is good!’” They liked our catch phrase and before you know it, people were coming around to see this shirtless guy juggle oranges.
“The guy needs money! The guy is good!”
“The guy needs money! The guy is good!”
Most of the people could see that I was a no-talent, drunken loser, but occasionally a charitable passer-by would drop a few coins into my hat (no doubt out of pity) and I’d say, “Hey! There’s a juggling fan!”
I juggled for about half an hour, occasionally dropping the oranges on the ground. Towards the end of my performance my oranges had suffered so many drops that I was basically juggling orange pulp.
Most of the tourists had left the square and orange juice was running down my arms and bare midriff, so I collected the money from the hat.
I gave Jason and Casey a dollar each for their chanting assistance, covered my $1.50 opportunity cost of the oranges, and still had $1.35, enough to buy myself a conch fritter for the walk back to the hotel.
Being a street performer is one of my all-time favorite bucket list check-offs, and for sure the most fun I ever had making $1.35.