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Longstreet Highroad Guide to the Florida Keys & Everglades

By Rick Ferren

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Florida Keys & Everglades > The Lower Florida Keys > Key West

Key West

[Fig. 8] In a way, Key West defines the spirit, the history, and the mythology of the Florida Keys. If you missed something during the drive down through the islands, you'll find it in Key West.

If you flew into Key West, you can find everything the Florida Keys have to offer within the island's 2,987 acres, except maybe solitude. And even that can be found when you take to the water, or plunge beneath the surface into another world. Click here for a new window with a larger version of this map.

The island is here for you, the tourist. Your visit, and that of millions of others each year, is the industry of Key West. Museums, scuba diving, deep-sea fishing, eco-tours, historic buildings, street entertainers, fine restaurants, shopping and more shopping, parasailing, boating, and bird-watching—it's all here, at your doorstep.

You can spend days just walking around Old Town, from one marvelous spot to another. From the Hemingway House to Sloppy Joe's, from Mallory Square to the Hard Rock Cafe, there's an endless number of sights, and shops, and great treats to sample along the way.

While you're here you may have to learn drink names like a Sloppy Rita or a Pan Am Panic, or you may find yourself out of costume during the world famous fantasy fest, or you might have to face an irresistible urge to never leave this tropical paradise. But these are the risks you take on a visit to Key West.

After crossing Cow Key Channel (MM 4), you're on the brink of Key West. The first thing you'll encounter is a major intersection where the road forks left and right. Most of the attractions including the Southernmost Point and Mallory Square lie at the other end of the island.

If you bear to the left at the junction, you'll be on South Roosevelt Boulevard (A1A), which takes you past Atlantic Ocean beaches and the airport. If you continue to bear to the left at the next few intersections and follow US A1A, you'll eventually come to the Southernmost Point in the continental United States.

If you turn right when you first come onto the island, you'll remain on U.S. 1, which continues as North Roosevelt Boulevard, a multilane commercial strip skirting the Gulf of Mexico. (If you do plan to turn to the right, all the locals know you should get in the right-hand lane before crossing the bridge.) After dozens of traffic lights and hundreds of neon signs, the boulevard eventually narrows into Truman Avenue and takes you into Key West's Old Town.

At Whitehead Street turn left to go to the Southernmost Point or right to Mallory Square and two public parking areas. There's also plenty of metered street parking available; the farther away from the square you get, the more likely you are to find a spot. But take note of which street you're on, and which turns you take when walking; the old narrow streets can tend to look alike to the newcomer.

Like Savannah, New Orleans, and Charleston, Key West is one of those special American cities that feel so different, so foreign, so out-of-synch with the mainstream, you wonder whether you should have brought your passport and a phrase book.

Depending on which way you hold your map, Key West is the beginning or the end of the Florida Keys. If you've been driving the length of the Keys you'll want to know that the Overseas Highway's Mile Marker 0 is at Fleming and Whitehead streets, near the Hemingway House in Old Town. From here it's 126 miles north to Florida City on the Overseas Highway. The Mile Markers are the original Mile Markers from the Flagler Railroad.

The road brings millions of visitors to the Keys every year. They may stop and dally awhile at Key Largo, Islamorada, Marathon, Bahia Honda, and Big Pine Key, and some may not make it to Key West. But as the sign in front of City Hall proclaims, Key West is "The End of the Rainbow," and although it may be a zany, eccentric, let-it-all-hang-out pot of gold, those who seek it are rewarded.

Key West's international stewpot has been simmering for hundreds of years. When the first Europeans set foot here, the island was covered mainly by low, dense bushes. The tall palm trees, fruit trees, flowering plants, and lush vegetation that now characterize the city were brought in from the Caribbean. Dr. Henry Perrine introduced many of these plants to the Keys in the late 1830s.

The island's original settlers were Calusa Indians, who lived here more or less peacefully until Spanish explorers showed up in the early 1500s. The Spaniards discovered piles of human bones littering the island and named it Cayo Hueso, "Island of Bones."

By the mid-1700s, European contact, which brought disease and slave traders, had decimated the Calusa population. Key West was reported to be one of their last settlements. It was abandoned in 1763 when England gained control of Florida from Spain.

When the English arrived in the 1700s, they anglicized the morbid Cayo Hueso to the more inviting Key West, although the Keys' most westerly islands are actually the Dry Tortugas, 70 miles over open water from Key West.

Key Westers are fond of calling themselves Conchs (pronounced konks), after the magnificent pink-shelled mollusks that tourists love to haul home. By some accounts, the original Conchs were British Loyalists who fled the 13 colonies during the American Revolution. Under the pledge, "We'd rather eat conchs than fight Mother England," they settled in the Bahamas and later migrated to Key West.

The appellation was often used in derision. In more recent times, however, Conch has come to mean a lifelong resident of the Keys, although Key West sticklers insist it's a badge that can be worn only by someone actually born on their island. In the meantime, conchs (the mollusk) are served in salads, frittered, stewed, and steaked.

In 1822, a Spanish nobleman who'd been awarded the island by his government in 1815 was so disillusioned with its heat, mosquitoes, fevers, and lack of fresh water, he sold it for $2,000 to Alabamian John Simonton. (A major Old Town street is named for Simonton.) A United States Navy presence was established and Key West was chartered as a city.

At the time pirates operating out of safe havens in the Caribbean were a serious menace to the fledgling town's existence, preying on merchant ships traveling the Florida Straits. In their swift, low-draft boats, they ambushed heavier ships wallowing in the shallow waters. Virtually uncontested, they seized goods, plundered, and murdered.

By the mid-1820s, the situation had become so critical that President John Quincy Adams sent Commander David Porter to rid the shipping lanes of the menace. Porter employed a fleet of mobile, light-draft schooners and a ferry boat requisitioned from New York City and was able to put the buccaneers out of business. However, sic transit gloria, so fleeting is fame, Porter was later court-martialed for chasing the pirates all the way into Spanish territory in Cuba and the Caribbean.

The pirates were replaced by "wreckers," members of a legalized industry that rescued passengers and salvaged the cargoes of ships that ran aground on the reefs and sand bars. According to the law, wreckers were entitled to 25 percent of everything they salvaged, but apparently they didn't always come by their cut on the up-and-up. Many ship captains claimed their saviours were no more than licensed pirates who even set strategically located fires to lure storm-threatened ships into dangerous waters.

From the early 1830s to the mid-1850s there were so many shipwrecks that Key West grew and prospered from the wrecking trade. The population increased to nearly 3,000 as New Englanders and British from the nearby Bahamas rushed in to take part in the lucrative enterprise. Key West became Florida's largest city and for a brief time one of the wealthiest per capita in the entire country.

Wrecking's heyday was over by about 1860. Lighthouses had finally been erected throughout the Keys and, along with improved navigation charts, were keeping new steam-powered ships out of harm's way. In wrecking's wake, other industries were spawned. Green turtles abundant in the Gulf of Mexico were harvested, canned, made into soup, and shipped from the island, to the point of near-extinction.

Harvesting sponges from the sea bottoms also put a jingle in the islanders' pockets. But, by the early 1900s, the overzealous spongers had nearly wiped out the supply. The divers moved on to Tarpon Springs, on Florida's west coast, where they prospered until the late 1930s, when a blight killed off most of the sponges and reduced the industry to a tourist attraction.

After the Civil War, thousands of Cubans fleeing their homeland's struggle for independence from Spain brought the cigar-making industry with them to Key West. By the turn of the century, more than 150 operations on the island were supplying much of the world's demand for quality cigars. But, like the sponging industry, cigar makers pulled up stakes and moved on to the west coast and made Tampa's Ybor City America's cigar city. Cubans who stayed behind have left their indelible mark on Key West.

On January 22, 1912, Key West's isolation from the rest of the world ended with a festival of marching bands, ship whistles, overblown rhetoric, and shouts of adoration from the townsfolk.

Henry Flagler's Florida East Coast Railroad, with the venerable, 82-year-old, almost blind and deaf, great man himself riding in triumph in his private car, entered the city. To the wildly cheering populace he proclaimed, "We have been trying to anchor Key West to the mainland, and anchor it we have."

With his dream fully realized, Flagler died peacefully in May 1913. His railroad brought boom times to Key West. Passengers and freight could now travel in two days between New York and Key West and continue to Havana on ferries that carried the cars across 90 miles of open water. The catastrophic Labor Day Hurricane of 1935 blew away the railroad, but three years later the Overseas Highway (US 1), built on the railroad's bones, was opened to tourist-bearing automobiles.

Tourist numbers remained small, however, and the island's businesses suffered the same bankruptcy problems suffered elsewhere during the Great Depression. Over the years the island has also attracted a number of literary lions: Ernest Hemingway, Tennessee Williams, Truman Capote, John Hersey, Gore Vidal, and Carson McCullers sought inspiration from the tropic vibes.

The early nineteenth century island of Key West was probably one-third to one-half the size it is today. As the population grew, ponds and lagoons were filled in for houses, businesses, and docks. Periodic hurricanes have had a hand in reconfiguring the island. So did Henry Flagler. When Flagler learned that there was no dry land in the city for a terminal for his approaching railroad, he ordered the filling of about 140 acres on what is now Trumbo Point.

Before World War II, Key West was a city of small wooden houses in a forest of exotic trees and red, yellow, pink, and white jacaranda, poinciana, frangipani, and bougainvillea flowers. There was no freshwater pipeline from the Florida mainland until early in the war, when increased military presence gave it a high priority, so each house had a cistern to collect rain water to supplement ground wells. The city had no sewer system, only a few houses had indoor plumbing, and outhouses and cesspits were the rule for most of the population.

Self-reliant Conchs depended on fishing and usually had at least one Key lime tree in their yard. The fruit was used for the Keys' famous pie, and the juice went into drinks and marinades for poultry, fish, and meat. Key Westers also grew Spanish limes, sapodilla, sour oranges, bananas, Jamaica apple, avocados, and mangos.

With the economic benefits from the Navy's heightened presence during World War II, the island began to modernize its infrastructure, a process that continues today. Tourists who began arriving in a trickle in the 1950s now arrive like a year-round tidal wave from around the world.

Drug smugglers also found the Keys a lucrative place to ply their trade. In response, in April 1982 the U.S. Border Patrol set up a blockade on US 1 at Florida City in order to trap drug smugglers using the Overseas Highway. Every vehicle approaching the roadblock was stopped and searched. The small number of arrests and confiscations was mitigated by a horrendous traffic jam that had thousands of cars and trucks backed up for miles.

Key West citizens, declaring that they were being treated like a different country, seized upon the road block as an opportunity for some fun and a party. A mock-secession conclave was called, and a flag with a big, lustrous conch shell as its centerpiece was created and raised in Mallory Square. The Conch Republic was born and quickly surrendered, making itself eligible for "foreign aid" from the notoriously generous U.S. government. "Conch Republic Days" is now an annual April happening.

Nowadays, visitors on extended holiday, taking in the island at a properly tropical, leisurely pace, are joined by daily throngs of cruise ship passengers, who rush down the gangways on a frantic mission to see it all in the few hours before the Royal "Whatever" sails onto Nassau or Cozumel.

Most of them never stray very far from Duval Street. From the Gulfside Pier House to South Beach and the Southernmost House on the Atlantic, Duval is one of the most eclectic, nonstop, energized miles in America (also, some say, one of the tackiest and tawdriest).

It's a neverending carnival, a sensual fiesta, a pedestrian river that flows at high tide around the clock. Posh apparel boutiques, art galleries, gift shops, and hip department stores like Fast Buck Freddie's stand side-by-side among an endless number of shops selling the same T-shirts. Remodeled Conch houses, cigar makers' cottages, and new little malls sell yogurt, ice cream, conch fritters, sponges, racy lingerie, books, dive trips, kayak trips, fishing trips, parasailing, excursions to the Dry Tortugas, bagels and cappuccino, real estate, pizza, pottery, Key lime pie, and Peking duck.

There are small hotels like the revamped Cuban Club, and the La Concha, a seven-story skyscraper now flying the Holiday Inn flag, that has seen the street through boom, bust, and boom since 1924. Some of the island's very oldest homes and churches, like the blinding-white St. Paul's, also knew the old town when it was just a town at the end of the railroad, not a tourist haven.

Attractions include The Wreckers Museum in the town's oldest house and the more recently established Ripley's Believe It Or Not! Odditorium. At restaurants by the score you can sit at a raw bar overlooking the street and gulp oysters by the dozen, or up the ante in more formal rooms and lushly planted courtyards with pricey French and Italian cuisines, plus steaks and seafood fixed every way imaginable.

Menus are often conveniently posted by the sidewalk. You can stroll along, enjoying the shops and the crowds, while choosing the perfect meal from dozens of offerings.

Of course, there are bars, bars, and more bars. Gay bars and mixed bars. Darkly lit bars with alluring corners and racy shows. Open-air bars, where music, hawkers, and wafts of cool air lure you from the hot crowded sidewalks. Old-time favorites like Sloppy Joe's, Captain Tony's, and the Green Parrot, where Papa Hemingway boozed and brawled. Jimmy Buffett sometimes does a surprise drop-in to the delight of patrons at his Margaritaville Cafe.

Tourists glad to see a familiar face and other elements rush to Planet Hollywood, Hooters, and the Hard Rock Cafe. If you don't want to walk, rent a bike, a moped, or roller blades. The streets are filled with a constant traffic jam, and parking is usually limited to somewhere not close to where you want to be.

A few steps off Duval Street and you're at Mallory Square, Mel Fisher's Maritime Museum, Harry Truman's Little White House, the Key West Aquarium, the Sponge Market, Hemingway's House, the Lighthouse, and the Southernmost Point.

After a few days of encountering fellow travelers from Alabama, Australia, and points in between, you might begin to wonder where all the bartenders, shopkeepers, hawkers, and other permanent residents live. The answer lies in the residential areas on either side of Duval. On Fleming, William, Petronia, Angela, Thomas, Olivia and dozens of other quiet streets, where tourist feet seldom tread and where residents are busily rehabbing the decreasing number of fixer-up Conch and gingerbread Caribbean houses. Many of the residents frequent their own restaurants, Cuban and Bahamian grocery stores, bars, and hangouts.

Bahama Village is one of the best places to encounter the real, old Key West. On the island's southwest side, bounded by Duval, Angela, and Louisa streets, it's like an old untouristed neighborhood in Nassau. Dogs, children, chickens, and roosters run in the streets and in swept-dirt yards in front of wooden houses painted turquoise and white. People dress up for Sunday services in simple white frame churches, patronize small grocery and merchandise shops, play cards, and gossip, seemingly oblivious to the tourist hubbub just around the corner. If you need a goal, go for breakfast, lunch, or dinner at Blue Heaven, at Thomas and Petronia.

Dozens of Old Town's most attractive Conch homes are on the small streets and alleys bordering the City Cemetery. Pick up the Pelican Path, a free descriptive folder of many of these houses produced by the Old Island Restoration Foundation, at the Chamber of Commerce Visitor Center in Mallory Square at 402 Wall Street. Phone (305) 294-2587.

By most accounts, Key West is cleaner and more prosperous than at any time in its history. A modern sewer system has virtually eliminated cesspits. But observers also say that the root of that prosperity may also be causing the city to lose much of its unique, appealing character.

The city's economy depends almost solely on tourism. Each year the resident population of 27,000 is impacted by more than 1 million visitors. Unwittingly, the golden goose of tourism is degrading the quality of the environment by using resources and triggering construction of hotels, shopping areas, and other developments that erase more of the city's dwindling green spaces. With land at a premium, much of the island's garbage is hauled to landfills on the mainland. The city's middle class is becoming a threatened species. With an average wage of about $7 an hour, thousands of service workers find it difficult to locate affordable housing. Even small apartments rent for $900 to $1,000 a month, and Conch houses that sold for $30,000 to $40,000 a decade or so ago now go on the market for upwards of $200,000. Surging development, coupled with skyrocketing property values, is endangering traditional older neighborhoods like Bahama Village. The cost of food, gasoline, and other necessities is also above the national average.

The city's liberal, live-and-let-live attitude has welcomed a gay community that makes up about 25 percent of the population. Tourism efforts include promoting Key West to domestic and overseas gay markets as well as to traditional outlets.

No matter when you visit Key West, there's bound to be a festival just ending or coming up soon. In winter, the big events are house and garden tours, literary seminars, and the really big Old Island Days Festival. Spring means the Conch Republic Independence Celebration, Key West and Lower Keys Fishing Tournament, and Key West Music Festival. Fireworks explode on the Fourth of July, the same month that Hemingway Days fills the streets with lots of "Papas." Cooler weather ushers in the theater and cigar festivals and Christmas celebrations.

For more information: Key West Chamber of Commerce, 402 Wall Street, Key West, FL 33040. At Old Mallory Square. Phone (800) 527-8539 or local (305) 294-2587.

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