Walking and Drinking Beer with the Wreckers, Rebels and Rumrunners of Key West
The six-foot-two-inch female impersonator in the gold lame gown 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.
And, of course, it’s also attracted tourists. Today, tens of thousands of them flock to Key West on frantic day trips from cruise ships, barely making it past the bars and souvenir shops on Duval Street to hurriedly buy a Sloppy Joe’s t-shirt or Margaritaville shot glass.
Nothing wrong with that, of course, but Key West is best enjoyed at a slower pace. Instead of looking at your watch so as not to miss the last launch back to the ship, you should be bicycling down the back streets past pastel-colored mansions, dining on the wharf under moonlight or sunning on a beach beside a Civil War fortress. Or of course, walking and drinking a beer along the harbor past the second largest schooner fleet in the nation.
With gas prices at record lows, this is the year for a road trip down Highway U.S. 1 to the southernmost point in the nation — especially since this “road” trip spends 15 percent of its time on water.
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 crazy millionaire who made all of this possible. http://www.pigeonkey.net/
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 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 September 2, 1935, when a hurricane and 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.
Driving U.S. 1, which for the most part is just two lanes, can be slow, but there are enough 1940s tourist attractions including giant shells, 30-foot high pirates and huge cement dolphins, as well as pull offs for beaches and parks, to keep it interesting.
If you’re driving straight through to Key West, Islamorada at MM 85 makes a good lunch stop. The Islamorada Fish Company offers alligator, grouper and cracked conch on a deck overlooking the water. It’s part of the Bass Pro Outlet here, which is worth a look to see Hemingway’s personal boat, Pilar, with is rather bizarrely placed in the middle of the store. God knows what Hemingway would have thought of that.
Islamorada is called the “sport fishing capital of the world,” but you might have to share your catch with the pelicans that are everywhere. Just off the coast is the San Pedro Underwater Archaeological Preserve – the final resting spot for 21 Spanish galleons that sank in a 1733 hurricane. Hurricanes have been bad news here for a long time.
Old Town Key West
The first thing to do in Key West is park the car. You won’t need it again until you leave. 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 nuts.
It’s been home to wreckers and spongers, Cuban cigar makers and New England fishermen, spongers from the Bahamas and a crazy assort of writers, poets, gays and eccentrics…all of whom have left their mark on the look of the place. 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 on the houses was done by out-of-work boat builders, so there’s a unique hand-crafted, wood “Conch House” are on nearly every block. And, it’s easy to believe, a ghost story behind every one.
Pick up a copy of Sharon Wells’ Walking & Biking Guide to Historic Key West, perhaps the best and most detailed free tourist guide produced anywhere (also on line at http://www.seekeywest.com/). It’s available at racks around town and in bars and restaurants. She provides 14 walking and biking tours with an exhaustive amount of detail. You’ll never be able to do it all — or even follow her crazy directions –but if you really want to know the history of that strange, Classic Revival pink house on the corner, this guide will tell you.
The north side of the island has most of the action, centered, naturally, around the cruise ship docks and the historic seaport. 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 is decidedly more noisy, crazy 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 Hemingway drank rum mojitos at — is now Captain Tony’s Saloon, a gay bar). Have a second obligatory beer at the Hog’s Breath Saloon, after which you can relax and discover you own places.
The Green Parrot is wonderful (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 with decent beer and wonderful food, all owned by actress Kelly McGillis, star of Witness and Top Gun. http://www.kellyskeywest.com/
I liked the waterside setting and pub atmosphere of The Schooner, where from our table you could hear the rigging creaking in the nearby boats, but there’s no shortage of bars. http://www.schoonerwharf.com/
No one said a thing to me when I walked the Harborwalk drinking a Guinness. There’s a number of outdoor bars along the pier selling everything from beers to frozen daiquiris at Mallory Square, and it appears that as long as you have your drink in a plastic cup, you can walk and drink on the streets to your heart’s content.
And of course, you will have to go Mallory Square for the sunset madness, at least once. It’s not as bad as you’d think for having a dozen mimes, jugglers, fire-eaters and pirates (frightening creatures dressed like Johnny Depp who come up behind you, say “Argggh”…and want a dollar to pose for a photo). The famous cat show is worth seeing, though you’ll want to throw the annoying Frenchmen through the ring of fire instead of the cat. But the sunset, with the schooners sailing back and forth in the foreground, the crowds and the craziness is now an American icon, right up there with the Grand Canyon.
As is posing for a photo at the Southernmost Point. When the cruise ships are in, there’s actually a long line of people waiting to pose by the 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 tour the homes of Hemingway and Audubon, 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 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, dream of discovering sunken treasure at Mel Fisher’s Shipwreck Museum, or even see an authentic shrunken torso that was once owned by Hemingway and is now, very appropriately, in Ripley’s “Believe it or Not” museum.
I gave the Pirate Soul Museum a look. Billed as the “Ultimate Pirate Museum!” it has Blackbeard’s weapons (they look like any other flintlock guns), and the only authentic pirate treasure chest in the world. Well, anything to do with pirates should be encouraged, but trying on pirate hats at the costume shop next door is more fun.
The Shipwreck Museum starts off with a dreadful bit of corny “living history” as “actors” portray the wreckers who once dominated Key West, but then they take you into the museum and the story is quite fascinating. 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 and it was highly competitive to watch the sea for wrecks. http://www.shipwreckhistoreum.com/
Why sea captains continued to sail in these waters, knowing that 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, strangely called both “the Gibraltar of America” and “the Forgotten Fort.” It never fired a gun in action. The trapezoid Civil War fort has brick walls five-feet thick and houses, as their guides will tell you, “the largest collection of Civil War artifacts in America.” Well…what the guides don’t tell you is that the artifacts, mostly huge canons, were used as land fill and were completely covered with cement. So you can’t actually see the largest collection of Civil War artifacts in America, but you can see where they were buried.
And it’s appropriate the fort in Key West never fired a canon because Key West is also the location of the shortest war in American history. In 1982, to stop alleged 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 residents of 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 that this is a strange and different land.