South By Key West

This past week, I took a much needed vacation. I know that everyone thinks my job is so easy because all I do is sit on my duff, tossing out olde tyme phrases, making references to old movies and TV shows that only I remember, and hanging up on strangers like Ernestine.

How Listeners Imagine Me At Work

But there is more to my job. First of all, you try being interesting for four solid hours. As I have proven repeatedly, that is impossible. Plus, how would you feel if every day you went to work and random strangers came up to you and called you fat or ugly or untalented and then you had to turn around and try to be hilarious? No wonder I need a Bloody Mary for breakfast. And so off to Key West I went.


I decided to make the trip something of an adventure by driving there from Ft. Lauderdale along the famous Overseas Highway. The first half hour, the view was spectacular and arriving as the sun set was something to behold. But by hour three, the journey took on a certain "are we there yet" quality. It was a once-in-a-lifetime experience, in the sense that I never need to do it again. But I am glad I did it once.

The first time I went to Key West was six years ago, the very same weekend, with my friend Clay. On a whim, we went there together, staying at the Island House in room 108. This is the best room in the house in my estimation because it is the one closest to the bar. This time, we were in the very posh owner's suite, which had a private balcony, a very intimate shower attachment ("Who cleans that?!" Clay asked), and your very own sling room with two slings. That just looked like a lot of work, or a nice place for two bottoms to relax and talk about their day.

It turned out that my friend Kevin from Chicago was in town during the same period, a happy accident I discovered in my Facebook news feed before I arrived. He and his friends had rented this awesome house with a guest house in the back and a pool in the middle. The house was like a younger, gayer version of The Big Chill but I can't go into further detail because Kevin repeatedly insisted that the whole trip was off the record. However, always mindful of the need to brand on the web, he did devise a clever photo project for all of us to participate in.

All the French I know

The En Vacance photo is an ingenious way to alert all of your Facebook friends that you are both unavailable and having more fun than they are. And we did have more fun than you. Kevin and his friends were a hoot. We danced the nights away at the Bourbon Street Pub, sang karaoke in Aqua and most delightfully danced a drunken afternoon away in their pool. When Clay and I walked down the street for reinforcements from the local liquor store we could hear "Call Me Maybe" down the block. So yes the rumors are true: my life is better than yours.

Naturally, I embarrassed myself repeatedly. While doing our best Solid Gold dancer impressions at karaoke, I went up to one of the other customers at the bar who I insisted looked so familiar that I was certain we had met before. "I'm the bartender at your hotel," he deadpanned. No wonder he looked so familiar. Sorry about that Shawn!

I was also recognized by some listeners at Bourbon Street Pub, but it doesn't count because none of my friends were around to see someone make a fuss over me. Honestly, the only good thing about this job is when a random stranger gets excited to see me and insists on taking a terrible photo of me in front of all of my friends who don't think I am the least bit famous. If a jaw drops and no one is around to see it, it doesn't matter.

Unfortunately, I left on Saturday before the notorious Bed Races. Clay and I saw them last time and it was pretty awesome. Of course it might have been helped considerably by the gallon of pina coladas we ingested. But the night before, celebrating the last night of my adventure, we all went to Aqua to see a terrific drag show, with a standout performance by Inga of Sweden, to whom I gratefully turned over every dollar bill I had. Later, while Kevin and his friends danced it out with a roving bachelorette party, I lingered around the back bar at Bourbon, talking to adorable bartender Wes, who has his name tattooed up the side of his torso in case you forget what to scream out while you are fucking him.

Wes was tasked with coming up with a signature shot for the post Bed Races crowd and decided that I would make the perfect guinea pig. Three test shots later, and I had to call uncle. I worried that I wouldn't make it back to the Island House in one piece. And I had a long drive back to reality in the morning. My three day adventure in the Keys was coming to an end. It was all a long way to go for a drink, but it was worth it.

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Read more of Derek's adventures in When Nightlife Falls and Colonnade: A Life In Columns. Both are available now On Amazon.com, and in digital form for The Kindle, The Nook, and in the iBookstore.