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 – 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.

Winter is the perfect time for a road trip down Highway U.S. 1 to the southernmost point in the United States – especially since this “road” trip spends 15 percent of its journey on water.

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 for 126 miles due south until dead-ending at the bottom of Whitehead Street in Key West. Along the way, the highway crosses 42 bridges – some 18.8 miles of open ocean water, including a spectacular stretch at Seven Mile Bridge, 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 eccentric millionaire who made all of this possible.

It was Flagler who had the inspiration and obsession to build a railway across the Florida Keys, stringing islands together a hundred miles out into the ocean. People thought he was mad. It took him seven years and a small fortune, but in 1912, a steam locomotive finally chugged across the sea and “Flagler’s Folly” became a reality. The tourist railway was a success until Sept. , 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. There’s nothing else quite like it in the world because Key West’s history has been unique.

It’s been home to wreckers and spongers, Cuban cigar makers and New England fishermen, spongers from the Bahamas and a crazy assortment of writers, poets, gays and eccentrics, all of whom have 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 shipbuilders, so there’s a Key West handcrafted, “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. This is the second-largest schooner fleet in the United States and sailing on them, or even just watching them sail, is a big draw.

Duval Street, the town’s main drag, runs the length of the island, but it is decidedly more noisy, crazy and decadent on the north side. You’ll have to have a beer in Sloppy Joe’s (where you’ll hear that the original Sloppy Joe’s – the one where local legend Ernest Hemingway drank rum mojitos – is now Captain Tony’s Saloon).

The Green Parrot is fun (once ranked as one of Playboy’s Top 20 Bars in the United States) and Kelly’s Caribbean Bar, Grill & Brewery is beautiful at night – an outdoor patio under trees of white lights, owned by actress Kelly McGillis, star of the movies “Witness” and “Top Gun.”

A visit to Mallory Square is mandatory for some sunset madness of jugglers, mimes, fire-eaters and pirates who turn out every night to join thousands to watch the sun sink into the sea. Another obligatory stop is posing for a photo at the Southernmost Point, a red, yellow and black buoy that, as the sign says, is closer to Cuba than Miami.

Key West Attractions

For such a small place, Key West has an incredible amount of attractions. You can tour 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 and ghost tours or sit on a rubber-wheeled train tour, 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.

Shipwrecking is an important theme in Key West. The Shipwreck Museum tells the story of the wreckers who once dominated the town. From its founding in 1822 through the 1850s, most people in Key West made their living as “wreckers.”

About once a week, a ship would run aground on the reefs that surround the island and the people of Key West would race to it in small boats to salvage anything they could from the wrecks, including gold, silver, china, silks, rum, fine wines and tea. Big towers were built in town where people would watch the sea for wrecks.

Why sea captains continued to sail in these waters, knowing that, on average, one of them would wreck once a week, is never fully explained. But apparently they did. So much so that, for 50 years, the 2,000 Key West salvagers had the highest per capita income in the United States.

At the edge of town, next to the largest beach, is Fort Taylor. It has walls five feet thick, but the fort never fired a gun in action. Which is appropriate, because Key West is the location of the shortest war in U.S. history.

In 1982, to stop drug trafficking from the Keys to mainland Florida, the U.S. Border Patrol put up a blockade on highway 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 and becoming 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 information

For more information on Key West, consult the Key West webpage or Florida Keys page.