The bright orange ball is sinking fast as the darkening ocean rushes to meet it. But the crowd at Mallory Square is torn between snapping photos of the stunning sunset and the distractions around the square. Escape artists, stilt walkers, musicians and magicians vie for the attention and dollars of the hordes of spectators who have wandered down to take part in the popular nightly ritual.

The scene is eccentric, touristy, and a totally Key West thing. Which is exactly why I’m here.

One weekend back in the early ‘70s, a struggling musician named Jimmy Buffet took a drive through the Florida Keys and found himself soaking up the sun and the rum in Key West. It proved to be a fortuitous stopover. He wrote a string of tunes about life in the slow lane that made his fortune and, ironically, revived tourism in the sleepy town.

After a year of emotional turbulence, Jon and I have come here to find our own Margaritaville.

You know that place – where flip flops are formal footwear, afternoons are spent lounging on a front porch drinking frozen concoctions.

 

And where a crisis is when the salt shaker goes missing.

 

After driving down the Overseas highway – that infamous ribbon of tarmac from Miami to Key West, we get to Key West just as a torrential downpour erupts. The roads become rivers, and traffic comes to a standstill. Then, suddenly, it’s over, and in a few minutes all evidence of the monsoon is gone. The sun reappears and the oppressive heat rises with a vengeance.

Flip flops as appropriate footwear – check.

We park outside the Speakeasy Inn and Rum Bar – our promising lodging choice for the next few days – and walk into the bar in search of a reception desk. The bartender greets us with a smile and hands us the keys to our room and a voucher for a free drink. “We have everything,” she says,” but our specialty is rum.”

She tells us a bit about the colourful history of the inn and the town. With only 90 miles of ocean separating Cuba from Key West, it was a popular hub for rum running during Prohibition. The inn was once the home of Raul Vaquez, a cigar selector at the Gato cigar factory. But his preferred source of income was running rum between the between Key West and Cuba, and he kept the inn’s cellar stocked with bootleg liquor. Raul was a popular guy and seems to have endeared himself to both sides of the law.

As we relax on the veranda sipping our margaritas (porch – check! Frozen concoction – check!), grateful for Raul’s entrepreneurial spirit and pondering our next move, the unique vibe of this little town at the end of the (American) earth starts to sink in. People wander by, mostly at a slow, meandering pace. Even drivers and cyclists don’t seem to be in a hurry. A few chickens scramble across the street, looking for cover from the unrelenting sun.

Wait, chickens? “Maybe some farmer left his coop open,” surmises Jon. “That’s a lot of chickens,” I reply, as a pack of the runaway poultry stops traffic as they make their way to the other side of the road.

In the hazy heat of the late afternoon, we rouse ourselves to take a stroll down legendary Duval Street – the main drag. An endless supply of shops hawks tee shirts, post cards, and souvenirs emblazoned with cigar, drug smuggling and Conch Republic themes.

We pass a couple of shops dedicated exclusively to the Key West chicken. Finally somebody clues us in. The prolific poultry have been roaming free for over 175 years. Their population increased dramatically in the 1950s, when thousands of Cubans landed on Key West’s shores as they fled the Revolution, their chickens in tow. The birds eventually made their way out of their pens and into the streets where they continue their free-range lifestyle.

We pass by Ernest Hemingway House – the author’s home before he packed up his second marriage and moved to Cuba. The stunning home is as famous for the resident six-toed cats (that are as prolific and the chickens) as it’s historical significance. Hemingway wrote The Snows of Kilimanjaro, To Have and Have Not, and countless other works here. Not surprisingly, his larger than life footprint is everywhere in town – mostly bars – and I suspect he must have been great pals with Raul of bootleg liquor fame.

We walk, and we walk. Reminders of the glory days of a by-gone era are everywhere, but instead of feeling contrived, it’s more like the eccentric personality of a favourite aunt.

As night approaches, the sound of music emanates from the bars tucked down the many side streets and laneways. We pick one and climb up the stairs to a small lounge. We plunge into soft cushions on the outdoor sofa and sip on cold mojitos while a blues musician bleeds his soul (strumming his six-string – check!).

Back at Mallory Square, in the growing darkness, another mellow day in Key West draws to a close. The crowds start to disperse in search of a meal, a drink, or a walk along the pier. Or their lost shaker of salt.

Margaritaville found – check!