Key West

Getting in touch with my inner Hemingway


Going to Key West

Information: Key West Chamber of Commerce, 800-527-8539,

Hemingway Look-Alike Contest: If you can’t make it to the look-alike contest, live webcam is available at their website beginning at 6:30 p.m. on July 19.


By air: American Eagle flies nonstop from Miami to Key West; United Express flies nonstop from Fort Lauderdale. Roundtrip airfare for the 50-minute trip starts around $100.

By land: Simply get in a car, and head south. Connect with U.S. 1 and continue as far as it goes. The 4-hour drive down the Keys is spectacular.

By sea: Key West Express operates high-speed passenger ferries from Fort Myers Beach and Marco Island. The ferry takes approximately 3 1/2 hours, and docks about a 15-minute walk from Sloppy Joe’s. 888-539-2628; Adult roundtrip fare $146.


Truman Hotel, 611 Truman Ave.; 305-296-6700; One of the only contemporary places to stay in Key West; beautifully decorated in a very quiet spot near the south end of Duval Street. Doubles from $169-$199.

Simonton Court Historic Inn & Cottages, 320 Simonton St.; 800-944-2687; Central location, with lush grounds and gardens in a restored cigar factory; the mansion, inn, and cottages all once housed workers. Doubles in summer approximately $190 to $260.

Blue Marlin Motel, 1320 Simonton St.; 305-294-2585; Just a block from the water in the South Beach area of the island, walking distance to everything at the south end of Duval Street. Doubles start at $97.


There are hundreds of bars and restaurants in Key West; here are a few personal favorites.

Six Toed Cat, 823 Whitehead St.; 305-294-3318; Excellent for breakfast and lunch, and with a picture of my “Ernie” still on the wall. $9-$16.

Blue Heaven, 729 Thomas St.; 305-296-8666; Dine inside or outside with the roosters, but duck the falling limes in the same Bahama Village space where Hemingway used to referee Friday night boxing matches. $8-$18.

Kelly’s Caribbean Bar, Grill & Brewery, 301 Whitehead St.; 305-293-8484; Just the best happy hour on the island, with $4 key lime margaritas and $4 fabulous wings, in the same building where Pan Am Airlines began in 1927. Happy hour 4-7 p.m. daily. Dinner entrees $15-$30.

Green Parrot, 601 Whitehead St.; 305-294-6133; Classic old bar, reputedly where Hemingway would stop for a nightcap when walking home from Sloppy Joe’s. Live music every night.

La Te Da, 1125 Duval St.; 877-528-3320; Three great bars, the outside Terrace Bar, the inside Piano Bar, and the upstairs Crystal Bar, with a drag revue.


Hemingway Home and Museum, 907 Whitehead St.; 305-294-1136; The ultimate Hemingway experience in Key West; not to be missed. $13 adults, $6 kids 6 and over.

Truman Little White House, 111 Front St.; 305-294-9911, Great historic tour of President Truman’s winter home starting in November 1946. $16 adults, $5 kids 5-12.

Key West Museum of Art & History, 281 Front St.; 305-295-6616; Lots of Key West and Hemingway memorabilia in the historic old Custom House. $10.

Key West Butterfly & Nature Conservatory, 1316 Duval St.; 305-296-2988; Stunningly beautiful butterflies and tropical birds. $12 adults, $8.50 kids 4-12.

Fort Zachary Taylor State Park, 601 Howard England Way; 305-292-6713; (find Fort Zachary in pulldown box). Admission $2.50 for one person on foot or bicycle to $6.50 for a carload of eight.

Fishing: Many charter and party boat options are available, but I liked Tortuga IV, 305-293-1189; A friendly half-day party boat that goes offshore every morning and afternoon. $55 includes all tackle.


 Highlights of Hemingway Days, July 17-22. Note that some events require pre-registration.


 Ernest Hemingway Home & Museum guided tours. 907 Whitehead St. Open 9 a.m. to 5 p.m.

Rarely exhibited Hemingway photographs and memorabilia. Key West Museum of Art & History at the Custom House, 281 Front St. Open 9:30 a.m. to 4:30 p.m.


  Introduction of contestants and previous winners of the Hemingway Look-Alike Contest. Doubletree Grand Key Resort, 3990 S. Roosevelt Blvd. 5:30 p.m.


 Key West Marlin Tournament first day of fishing. 8:30 a.m. to 4 p.m.

Sloppy Joe’s 32nd annual “Papa” Hemingway Look-Alike Contest, first preliminary round. 6:30 p.m.

“Hemingway On Stage: In Deadly Ernest.” The final segment of actor Brian Gordon Sinclair’s six-part one-man dramatic presentation on Hemingway’s life. Tropic Cinema, 416 Eaton St.; 8 p.m. $10 per ticket. 305-295-6616, ext. 106, or


 Key West Marlin Tournament’s second day of fishing.

“Hemingway On Stage: In Deadly Ernest” at Tropic Cinema. 11:30 a.m.

Papa Hemingway Look-Alike Fish-Off: Papas compete in dockside catch-and-release challenge using traditional Cuban yo-yos. Conch Republic Seafood Co. docks. 1:30 p.m. Free.

Sloppy Joe’s 32nd annual “Papa” Hemingway Look-Alike Contest, second preliminary round. 6:30 p.m.

Lorian Hemingway Short Story Competition winners announcement and reception at Hemingway’s first Key West residence, Casa Antigua, 314 Simonton St. 8 p.m. Free.


 Key West Marlin Tournament’s third day of fishing.

Caribbean Street Fair with arts, crafts, jewelry, tropical clothing and food. 10 a.m.-9 p.m. 305-292-8445 or

Photo opp with “Papas.” Greene Street outside Sloppy Joe’s. Noon.

Running of the Bulls: “Papas” dressed in their Pamplona best and a breed of “bull” found only in Key West. Outside Sloppy Joe’s. 1 p.m., followed by Hemingway’s birthday cake at 1:30 p.m. Key West Marlin Tournament awards banquet and silent auction (open to tournament participants and their guests only). Westin Key West Resort, 245 Front St.

Sloppy Joe’s “Papa” Hemingway Look-Alike Contest, final round. 6:30 p.m. Hemingway 5k Sunset Run/Walk through Old Town Key West. 7:30 p.m., with awards ceremony to follow. To register: 305-240-0727.


Sloppy Joe’s Arm Wrestling Championship. Registration 11 a.m., contest begins at noon. Sloppy Joe’s. $5 entry fee; free to watch.Screening of “To Have and Have Not” at Tropic Cinema, 416 Eaton St. Reception and silent auction at 7 p.m., film at 8 p.m. 305-292-8445.

Special to The Miami Herald

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?

Read more Florida Travel stories from the Miami Herald

Miami Herald

Join the

The Miami Herald is pleased to provide this opportunity to share information, experiences and observations about what's in the news. Some of the comments may be reprinted elsewhere on the site or in the newspaper. We encourage lively, open debate on the issues of the day, and ask that you refrain from profanity, hate speech, personal comments and remarks that are off point. Thank you for taking the time to offer your thoughts.

The Miami Herald uses Facebook's commenting system. You need to log in with a Facebook account in order to comment. If you have questions about commenting with your Facebook account, click here.

Have a news tip? You can send it anonymously. Click here to send us your tip - or - consider joining the Public Insight Network and become a source for The Miami Herald and el Nuevo Herald.

Hide Comments

This affects comments on all stories.

Cancel OK

  • Marketplace

Today's Circulars

  • Quick Job Search

Enter Keyword(s) Enter City Select a State Select a Category