Wreckers, rebels and rumrunners…historic Key West has attracted them all
Story and photos by Rich Grant
The six-foot-two-inch female impersonator in the gold dress curled her finger at me across Duval Street and shouted, “Come on over honey, the show starts in 15 minutes.”
She was wrong. The “show” in Key West started about 180 years ago and it’s still going strong.
This somewhat crazy tropical island, capital of the self-proclaimed Conch Republic, lies 126 miles from the southern tip of mainland Florida (making it the southernmost point in the nation). It's closer to Cuba than to Miami, and closer to another planet than to Mainstream America. Since it was founded in 1822, Key West has been home to a whacky collection of pirates, wreckers, artists, rumrunners, writers, sponge divers, cigar makers, ex-presidents, poets and musicians.
Highway 1 to Key West
There are 800 islands in the Florida Keys, but only 30 of them are inhabited. The Overseas Highway, also called U.S. 1, opened in 1938 on an old railway bed and stretches from Key Largo just off the mainland all the way down to the bottom of Whitehead Street in Key West. Along the way, the highway crosses 42 bridges spanning some 18.8 miles of open ocean water, including a spectacular stretch at Seven Mile Bridge. The latter is also known as Mile Marker 45 (miles are marked by how far you are from Key West, which has the distinction of being Mile Marker 0).
At MM45, you can walk on an old abandoned stretch of the bridge to Pigeon Key and a museum about Henry Flagler, the crazy millionaire who made all of this possible.
It was Flagler who had the inspiration and obsession to build a railway across the Florida Keys. People thought he was mad and it took him seven years and a small fortune, but in 1912 a steam locomotive finally chugged across the ocean and “Flagler’s Folly” was a reality. The tourist railway was a success until Sept. 2, 1935, when a hurricane and an 18-foot tidal wave washed over the keys, killing 800 people and wiping out the tracks and many of the bridges.
Key West was an island again…but only for three years and then the railroad was replaced with the auto highway.
Old Town Key West
The first thing to do in Key West is park the car. There are at least a dozen bike rental shops and everything is more or less within walking distance…provided you like to walk. The historic area is 4 miles by 2 miles, and runs from the Gulf of Mexico to the Atlantic Ocean.
It’s been home to wreckers and spongers, Cuban cigar makers and New England fishermen, spongers from the Bahamas and a batty assortment of writers, poets, gays and eccentrics…all of whom left their mark.
The architecture reflects everything from Victorian New England to the louvered shutters of the Caribbean, with a few New Orleans balconies thrown in. And of course in the tropical climate, everything is rotting to some degree. Much of the wood carpentry work was done by out-of-work boat builders, so there’s a unique, hand-crafted “Conch House” on every block.
The north side of the island has most of the action. Harborwalk is a maze of boardwalks that follows the waterfront. It’s lined with boats and bars and four great tall ships that go in and out of the harbor on day and sunset cruises. Duval Street, the town’s main drag, runs the length of the island, but it is decidedly more noisy, nutty and decadent on the north side. You’ll have to have the obligatory beer in Sloppy Joe’s (where you’ll hear that the original Sloppy Joe’s – the one where Hemingway drank rum mojitos – is now Captain Tony’s Saloon, a gay bar).
The Green Parrot is wonderful (it made Playboy’s Top 20 Bars in America), and Kelly’s Caribbean Bar, Grill & Brewery is beautiful at night – an outdoor patio
under trees of white lights (it's owned by actress Kelly McGillis, star of Witness and Top Gun).
And of course, a visit to Mallory Square for the sunset madness of jugglers, mimes, fire-eaters and pirates is obligatory. As is posing for a photo at the Southernmost Point, a red, yellow and black buoy that is closer to Cuba than Miami.
Key West attractions
For such a small place, Key West has an incredible amount of attractions. You can wander around Hemingway’s house, see the “Southern White House” of Harry Truman, go to art museums and art galleries, walk among butterflies or through an aquarium petting stingrays, stroll the town on historic walking tours, ghost tours and rubber wheeled train tours, sail across the bay on schooners or jet boats, lay on the beach, take a snorkeling cruise, climb to the top of a lighthouse or dream of discovering sunken treasure at Mel Fisher’s Shipwreck Museum.
At the edge of town, next to the largest beach, is Fort Taylor. It has walls five feet thick, but never fired a gun in action. Which is appropriate, because Key West is the location of the shortest war in American history. In 1982, to stop drug trafficking from the Keys to mainland Florida, the U.S. Border Patrol put up a blockade on the U.S. 1 and forced anyone traveling north from Key West to show identification that they were U.S. citizens.
Since the U.S. government was treating the Keys like they were a foreign country, on April 23, 1982, Key West Mayor Dennis Wardlow declared that Key West was seceding from the Union to become “ the Conch Republic.” A flag was created and war was declared. The Conch Republic immediately surrendered and demanded foreign aid.
Today, the Conch flag flies throughout town and you can buy any number of souvenirs (including a Conch Republic passport) with the country’s slogan, “We Seceded Where Others Failed.”
But Key West doesn’t need its own flag or passport. You only need to spend 10 minutes here to know this is a strange and different land.
More info: www.keywest.com and www.fla-keys.com
Rich Grant writes about other destinations at www.WalkingAndDrinkingBeer.com
