Quick Trips

Getting in touch with my inner Hemingway

I was sitting at the Green Parrot Bar, a place I’d heard described as “the definitive Key West saloon,” listening to the tourists seated next to me talk animatedly about coming to Key West every year just to see the Ernest Hemingway Look-Alike Contest, when one of them stared at my gray beard and went silent.

“You know, sir, y’all look a lot like Hemingway yourself — are you in the contest?” he asked. I smiled and told him that in fact I had entered the contest, which was to start that night at Sloppy Joe’s. He shook my hand and handed me a very expensive cigar “for good luck tonight.” A generous reaction to my quixotic entry into the look-alike competition, and a welcoming introduction to Key West in general.

It was July 2011. I had flown into Miami earlier that day from the Cayman Islands, where I had been scuba diving. Two other white-bearded gentlemen were waiting to board the turbo-prop flight. Quick introductions confirmed that indeed, we were all heading to Key West for the same reason. I sized them up during the stunningly beautiful flight above the azure waters off the Florida Keys and concluded that I looked as much like Hemingway as they did. My competitive juices were already flowing.

Now, I left the Green Parrot on my rental bike, the most convenient and fun way to get around Key West. Pedaling down Whitehead Street, I stopped at Hemingway’s house to channel a bit of Papa’s spirit and prepare for the evening event. Preserved just as it was when he lived there during most of the 1930s, it’s now a registered National Historic Landmark. The cats roaming the grounds, many of them six-toed, are supposedly descended from his cats. They reminded me of Ernie, my own six-toed feline.

The ride through the hordes of tourists crowding the bars and restaurants on Duval Street gave me time to reflect on exactly why I was entering this quirky event. It wasn’t any one reason but a confluence of many that led to my traveling from home in Southern California to the opposite corner of the country to participate: The recent death of a good friend who was a life-long amateur Hemingway scholar. The fact that this particular year was the fiftieth anniversary of Hemingway’s death. My own milestone birthday, the sixtieth, occurring just days after Hemingway’s. The recent release of the movie Midnight in Paris, with a young Ernest fulminating in Paris bistros. Or maybe it was just having a six-toed cat.

Arriving at Sloppy Joe’s, where Hemingway was a fixture in his day, I sought out Donna Edwards, brand manager for the bar and chief organizer of the contest, for a history of the competition. She explained that 31 years earlier, the manager and owner of the bar hit on the idea of the look-alike contest to try and promote some excitement and a few more patrons during the summer doldrums for tourism.

They clearly succeeded, as the competition currently attracts up to 150 entrants annually, some even from overseas. Many participate year after year, with no expectation of winning, just partying with their Papa friends.

“What I really enjoy is just the atmosphere and the people that attend,” said Edwards. “These guys are superstars of the week in town — people want their picture taken with them,” she added.

The main event

The look-alike extravaganza runs July 19-21 this year and is the centerpiece of an even larger Hemingway Days Festival, running July 17-22. Among the events are a $50,000 marlin fishing tournament; a sunset 5K run; an internationally recognized short story writing contest judged by Hemingway’s granddaughter, writer Lorian Hemingway; a book debut with Hemingway’s grandson, Edward Hemingway; a Caribbean street fair taking up much of Duval Street on July 21, and the always zany “Running of the Bulls.”

By now, Sloppy Joe’s was bursting at the seams with hundreds of well-lubricated patrons, half of whom looked something like Ernest. They spilled out the open doors and windows onto Greene and Duval Streets, awaiting the start of the festivities.

As I was alone, I sought out fellow contestants and was quickly adopted by a group from Texas. Richard Filip, a real estate executive from Houston, had an entire team with him for support, sporting T-shirts, campaign buttons, and banners. Upon learning I had no supporters of my own, they loudly declared they would root for me onstage, too.

Richard explained why he had entered the competition multiple times: “It’s the camaraderie, having my whole team here with me, the people you meet from different states — it’s just an interesting cross-section of all walks of life.”

The enormous crowd roared as the contest judges appeared on stage, carrying, of all things, a cake. It turned out to be a birthday cake with a likeness of Ernest, since that night was his birthday. Looking at the judges — all previous contest winners — I gasped. They were all, well, very stout, and very white of beard and hair. Being neither, I wondered about my chances.

Contestants were called up to the stage in groups of eight. When my turn at the microphone came, I tried to show my connection with Hemingway through various photos. One of me with Ernie, the six-toed cat. One of me fishing in my kayak. Other photos and vignettes, and finally, one of me climbing Mt. Kilimanjaro. “Not only have I have seen the The Snows of Kilimanjaro, I have been on top of Kilimanjaro,” I said.

They weren’t impressed; I didn’t even make it into the next round.

A close shave

Disappointed and fueled by mojitos, I found an all-night pharmacy and bought a beard trimming razor. The next morning, clean shaven except for a Heminwayesque moustache, I soaked my naked face in the warm waters of Fort Zachary Taylor Historic State Park beach.

Later that day, I made it to Sloppy Joe’s in time for the “Running of the Bulls.”

This daft event always occurs on the last day of the contest and features the look-alikes dressed as devotees in Pamplona, riding or pushing wheeled, wooden bulls on a mini-parade through Key West. Thousands of shouting tourists line the route, snapping pictures, waving cigars and swilling cocktails. I didn’t participate, but one of my new contestant friends told me that without the beard, I now looked like a “young Hemingway.”

The finals that night were raucous, and yes, the eventual winner really did look like Papa.

I finished my Key West Hemingway Days as he might have done by going offshore fishing the next day, catching a beautiful mangrove snapper. All of the restaurants along the wharf will prepare your catch for dinner; mine was done at the Half Shell Raw Bar for a mere $9, including all the sides. One of the best seafood meals I have ever had.

As I write this, the beard is growing gray again, and I’m readying my presentation to the look-alike judges. Maybe they’ll be more impressed with my recent trip to Hemingway’s house and favorite bars in Havana, Cuba?