North America | United States
July 24, 2008
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Key West

A journey down Highway One to America's southernmost tip.

Laid-back and over-easy

Bone Idyll

Of the many strange journeys to be made in America, one of the strangest is to follow Highway 1 from Miami to the southernmost tip of the continental US.

To be pedantic, that last statement is true thanks only to the highway engineers. For the final 113 miles of its length US1 (aka the “Overseas Highway”) runs far out over the sea, picking its way deep into the Gulf of Mexico along the slew of low coral keys (islands) that trail Florida’s southern tip. At its end lies fabled Key West, a mere 90 miles short of Havana and closer to Cuba than to the Florida mainland.


The start of the drive is low key. In fact, it’s deadly dull. Miami’s southern suburbs merge in a low-rise, low-interest urban prairie as far as the mainland’s last town, Homestead – flattened by 1992 Hurricane Andrew and rebuilt with all the flair of a McDonald’s.

After a brief respite as the road skirts the Everglades and hefts itself over a swamp-fringed channel onto Key Largo, normal service is resumed with relentless strip development whilst US1 island hops to Marathon, the cheerily redneck hub of the Middle Keys.

Seven Mile Bridge

Only then, just as you are on the point of despair, do things start to look up. Soaring serenely above the ocean, Seven Mile Bridge is shadowed by the gaunt remains of Flagler’s railroad, washed out with the loss over 400 lives in an earlier hurricane. On the far side – often beyond the limit of visibility – lie the pristine white coral beaches of Bahia Honda, the first of the Upper Keys.

To Key West

This lightly populated chain is a world away from everything that has gone before. From here on driving is pure joy. With the hood rolled down, the sky arches impossibly wide as a tropical sun throws up mirages of shimmering heat. Land and water mix in a maze of creeks, channels and tidal islets. Cormorants perch on the telegraph poles that stride across the sea, snakes bask on the roadway, and snapping turtles lurk in the pools. Pelicans, part-goose part-pterodactyl, swoop and dive overhead with a grace that belies their ludicrous clumsiness on land. Despite the distance from the mainland, the colours are of the swamp not the sea – sky of tarnished silver, water of burnished gold, both cut through with the vivid green of tropical vegetation. Stop the engine and the sounds are not the crash of surf, but the gentle lap of water underpinned by a steady insect drone. Only the salt in the air hints of the deep ocean.

Myths and legends

Four hours driving from Miami allows plenty of rumination. Key West is one of those travel names that carries baggage. Sometimes deliberately, it’s hard to disentangle history from myth. It’s true enough that at a time when Miami was still populated only by mosquitoes, Key West was the richest small town in America, with its own steamer service to New York. It’s true also that much of its wealth came from rum-running and wrecking – licensed salvage from the ships that came to grief on the Keys’ treacherous reefs. But much also came from cigar rolling, sponge diving and the US Navy, who used it as the base for their Caribbean anti-pirate squadron.

Likewise it’s true that Ernest Hemingway was numero uno soak at 'Sloppy Joe’s' - an old urinal still serves as a drinking fountain in Hemingway’s garden for the descendents of his beloved cats. It’s merely that 'Sloppy Joe’s' is no longer 'Sloppy Joe’s' but 'Captain Tony’s'. (Today’s 'Sloppy Joe’s' is a Johnny-come-lately impostor for the tourists.) Even the town’s name is not what it seems. Originally called 'Bone Island' - Cayo Hueso (pronounced 'wayso') by the Spanish, it became Key West only as the result of a typically linguistically-challenged Yankee misunderstanding.

'Fear This!'

Another chestnut is Key West’s more recent reputation as one of America’s quirkiest, most liberal settlements – a lingering consequence of its sixties status as a hippy Mecca. When I visited, it took precisely ten seconds for evidence in support to appear. Crossing the city limits past bikini-clad pickets protesting Iraq, my view was abruptly filled by a rear window screaming “Fear This!” as I was overtaken by a klaxon-sounding, bull-horned hearse turned motorhome.

Paradise lost and found

But Key West is actually a complete Jekyll and Hyde of a town. It is indeed a tropical idyll of immense elegance, with the largest historic district of any US town and some quite magical B&Bs and inns (courtesy largely of the town’s strong gay community).

However it has also become blue-collar America’s chosen place to let loose and kick back – hot and exotic, but safely free from Arab terrorists and suspicious plumbing.

Rum punch with apple pie

Thankfully it’s straightforward to escape the Hawaiian shirt brigade simply by avoiding Duval Street (the town’s main drag) and adjacent Mallory Square.

What’s left is a totally captivating townscape of 19th century white clapperboard mansions with deep verandas and lushly gorgeous tropical gardens, interspersed with banyans and guavas for shade.

As for mood, a unique mix of Caribbean informality and the peaceful calm of small town America prevails. This is a place where cockerels rootle in the cemetery, grannies with hair buns ride silver-tasselled bicycles, and leathery old sailors prop up the harbour bars eyeing the pelicans and the Dupont’s 200 foot yacht with equal disdain. As the locals have it: 'Enjoy!'

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