Keys in the Cays

Story by Ron Keys// Photos by Ron Keys
September 9 2010

I went down to Captain Tony’s to get out of the heat
When I heard a voice call out to me, “Son, come have a seat”
I had to search my memory as I looked into those eyes
Our lives change like the weather but a legend never dies
-Jimmy Buffett

As I sit at my table in Sloppy Joes at the corner of Duval and Greene Streets, my senses awaken to the lovely, statuesque waitress with the perfectly tanned legs that never end. She smiles at me and asks, “Would you like a margarita, sweetie?” I respond in my most masculine voice, “Yes, I’d love one of those…and could I have one of those Sloppy Joes too?” Her bronze skin and her beauty leave me a quivering pool of jelly. I can hear the band warming up in the background and the din of happy people carrying on animated conversations tells me that the cares of the world are left far behind at Sloppy Joes. As I survey the nostalgia suspended like memories from the ceiling and the walls, I’m jarred back to real time by the loud clanging of a ship’s bell, an audible “thank-you” for a generous tip received at one of the three bars.

On December 5, 1933, prohibition ended and the original Sloppy Joe’s Bar at 428 Greene Street opened, just a few steps away from its present location. It is said that Ernest Hemingway, who used to frequent it, suggested this moniker after a filthy dive in which he used to hang out in Cuba. In 1948, Anthony (Tony) Tarracino, son of a bootlegger from New Jersey, arrived in Key West with $18 in his pocket while running away from the mob. Tarracino became a shrimper and a gunrunner during the Bay of Pigs debacle. He was a charter boat captain for a while, a gambler, ladies’ man and raconteur. In 1961, Tony became the proprietor of the old Sloppy Joe’s location and changed the name to Captain Tony’s Saloon. Then in 1989, after several tries, he became mayor of Key West. He said later that it was the hookers’ votes that put him over the top. Four wives and 13 children later, Tarracino finally passed away on November 1, 2008, at the ripe old age of 92. Jimmy Buffett, who used to sing at Captain Tony’s for five bucks and a free Bud, says it all in this chorus about Tony’s life:

He said I ate the last mango in Paris
Took the last plane out of Saigon
Took the first fast boat to China
And Jimmy there’s still so much to be done

Circumstances have placed me in Florida for a mini-vacation, so I’m southbound on Florida’s Turnpike with Miami in view and a rendezvous with my old friend Dave. Miami, with America’s third-largest skyline, glistens in the bright sunshine as Dave and I walk alongside the Miami River toward South Beach. Strolling along the beach, I notice that many of the lovely tanned female bodies are adhering to Miami’s minimalist textile mindset. I wholeheartedly agree with their philosophy and I hate to leave. We pass along Ocean Drive, which is quiet now, but when the sun goes down, these outdoor patios fill to capacity, and who knows which movie stars you may see on any given night.

The next morning I arrive early at Peterson’s Harley-Davidson ( on the Old Dixie Highway in South Miami. Tracy Morehouse, Peterson’s rental girl, has a silver Harley-Davidson Electra Glide Classic all ready for my two-day ride out to Key West. Peterson’s and Tracy have been very helpful, and if you’re ever in South Florida and looking to rent a bike you know where to go. After a little spin around the parking lot to prove that I know how to ride, I’m southbound on U.S. 1 to the most southerly point in the continental United States.

It’s close to 32*C (90*F) and I feel like an anomaly here, with my full-coverage helmet, leather gloves, and armoured mesh jacket. Everyone is riding bareheaded without any protective gear. With 46 years of riding experience, I’ve witnessed too many disastrous results of not wearing proper attire while riding.

I ride through Homestead, the last city on the mainland before entering the Keys, and remember the 1992 Category 5 hurricane that killed 65 people and devastated everything in its path. Now it looks as if nothing had ever happened.

As the Harley thrums along, I enter the Keys as I cross the first bridge at Jewfish Creek and a sign proclaims it is now 108 miles to Key West. Key Largo is the first of the many cays, which is the Spanish word meaning a small island of sand or coral. Since this entire area was once Spanish, only the spelling of the word has changed, but the pronunciation remains the same. My attention is drawn left and right to the opulence and materialism that consume the moneyed people who have vacation residences here.

I slowly cruise along, and on either side I see evidence of the land wrestling with the sea for dominance. Mangroves are everywhere with their tangled roots set deep into the saline ocean floor. Bits of sand and organic material become trapped, depositing themselves in the tangle of roots providing nutrients, and eventually another island is formed. The Florida Keys are a chain-like cluster of about 1700 islands which divide the Atlantic Ocean from the Gulf of Mexico. Fishing in this habitat is among the best in the world, as fishing charters advertised everywhere along my way attest.

Suddenly, on my left, I see a monument. I’m a sucker for monuments and historical plaques, so I make a U-turn and go back. On September 2, 1935, the first of three Category 5 hurricanes ever to hit the United States in the 20th century, “The Labour Day Hurricane,” came ashore in the Upper Keys and rapidly intensified. A storm surge of 5.5 to 6 metres (18 to 20 feet ) hit Islamorada, leaving death, destruction and mayhem in its wake. Over 400 people were killed in the disaster. Hurricanes Camille in 1969, and Andrew in 1992, were the only other Category 5 hurricanes to hit the continental United States. (It wasn’t until World War II that hurricanes were given the names of women, and because of demands for equality, in 1978 male names were also adopted.)

As I ride out of Key Largo, the lush green vegetation along the roadside obscures my view of the nearby ocean on either side. Here and there, tall, stately palms, bent over by prevailing winds, stand like drunken pirates wearing green party hats. The Islamorada Fish Company Restaurant and Market comes into view on my right, and I pull into the lot and park the Electra Glide. In a sweaty rush, I make a beeline for the front door and the awaiting air conditioning. All manner of fish and creepy crawlies that live in the sea are on display, packed in ice and ready to take home. I walk outside again and there, on piers over the water, covered with a steep-pitched, log-framed roof thatched with reeds, is the restaurant. Along the plank walkway that leads to the restaurant is a screened-in area of seawater filled with very large fish. I watch for a few minutes as departing customers dally while throwing leftovers into the water and the fish swirl about in a feeding frenzy grabbing what the seagulls don’t get first.

I’m throbbing along at about 2000 rpm in sixth gear, rigorously observing the posted speed limit and watching for those tourism guys. I’ve been told that should my throttle hand become impetuous, they would take great delight in reminding me of my lack of attention. I see federal and local tourism guys in abundance, doing their jobs, stopping locals and tourists alike and welcoming them to Florida’s Keys with their red lights flashing.

With Key Largo and Islamorada in my wake, the keys ahead of me are somewhat smaller: Fiesta, Conch, Duck, Grassy, Vaca, Boot and Knights Keys roll by. The cloudless sky is reflected in the sea and the water is so clear that I can see the sandbars and coral beneath the choppy water.

Seven Mile Bridge parallels the old railway with its continuous sea-level arches. This was the first link between the mainland and Key West that enabled the transportation of people and goods back and forth. The great American capitalist Henry Morrison Flagler built resorts and railroads in Florida to promote tourism, but the Labour Day Hurricane destroyed much of the fruits of his labour. The government replaced the railway, using parts of the old bridges to build the auto road to Key West. What remains of the old railway bridges is now used as walkways and places for fishermen to try their luck. I stop on the bridge to take a photo, unaware of signage that precludes me from doing so. Luckily, none of those tourism guys with the red roof lights were around.

After crossing Seven Mile Bridge, I’m now in what is referred to as the Lower Keys, and as I pass by the entrance to Bahia Honda State Park on Deer Key, I remember being told that I should adhere religiously to the posted speed limit. This area is home to the Key Deer, which are tiny little creatures about the same size as a Doberman. The highway here is bounded by a high black chain-link fence to protect the deer, and at every entrance there are cattle grates on the ground that prevent them from walking out onto the roadway. At night the deer are in abundance and quite approachable, but I don’t catch a glimpse of these tiny little guys as I ride along.

At Key West, I trundle along Roosevelt Boulevard and arrive at land’s end. My destination for the night is Eden House on Fleming Street. As I walk between the white pillars with light-green trim that support the second-floor cantilevered balcony, and through open doors, my attention goes to the wide wicker blades of the whirring ceiling fan in the open-air lobby. Catherine greets me at the front desk and shows me my room and all the amenities of Eden House ( Built in the 1920s, it is one of the oldest hotels in Key West. I divest my saddlebags and trunk of all my belongings, park the bike in the provided safe place and relax in my air-conditioned room to cool off. With its quaint historic charm, southern hospitality and proximity to downtown, this is a great place to stay.

Later I walk out onto Fleming Street with map in hand. Scooters, the favourite means of transportation, zoom here and there at full speed. As I slowly walk along, my senses are awakened by a horticultural profusion. Trees in full bloom perfume the air I breathe as I slowly stroll along, their vines covering white-stuccoed walls, their flowers in the most iridescent reds, violets, oranges and blues. Palms trees stand erect with their green fronds spread like peacocks inside a black wrought-iron fenced garden. Brightly painted homes with second-level balconies and extravagant embellishments line the street. This is the look of Key West.

At Duval Street, I turn right and walk toward the sea. It’s not too busy today, but I’m told that it picks up in the evening. I walk past a lady of the evening and a scantily clad girl, her body embellished with tattoos, beckoning me to come inside the Red Garter to see the girls. I pass on that one.

The open doors of Captain Tony’s Saloon welcome me in, and as I look up, every square inch of the ceiling is covered with business cards except for one sweet area. I walk over and sure enough, it’s just as I thought – this area is covered with ladies’ brassieres. I’m sure if those bras could talk, each one would have an uplifting story to tell. I can only imagine what a hot spot this must be late into the evenings.


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