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Originally settled by Calussa Indians, Spanish conquistadors attempted to seize this prime real estate in the Southwestern Keys. The beaches became the burial grounds for many of the natives, giving the island the name of Bone Island; Key West in Spanish. The English changed this name to Key West.

John Simonton, an American businessman, bought the island from Juan Pablo Salas and developed the island with the help of Greene, Whitehead, and Fleming. They encouraged the Navy to open a base to combat piracy in the area.

The island prospered because the coral reefs brought many ships to Davy Jones Locker. Many became millionaires saving the many shipwrecks. At one point, the people of Key West became the wealthiest city per capita in the United States.

Henry Morrison Flager, against all odds and better judgment, built a railroad from Homestead to Key West. The first train arrived on January 22, 1912. It connected the mainland with Key West. From Key West, Havana Cuba was only ninety miles away. Considered the Eighth Wonder of the Modern World, the Overseas Railway crossed 42 stretches of sea with tracks and bridges, the longest being seven miles. From 1912 to 1935 Key West exploded as a business and tourist center. A major Class Five hurricane destroyed much of the track in 1935. Once again, Key West was cut off from the mainland.

The state of Florida purchased the Overseas Railroad right-of-way and converted it to Overseas Highway in 1938, using the roadbed and bridges that Henry Flager built.

World War II brought new prosperity to the island with the Naval Base. Ernest Hemmingway and Tennessee Williams resided on and visited the island. Cuban tobacco became handmade cigars.

In 1981, the United States government installed roadblocks near Key Largo, cutting off tourist trade to Key West. I’m not quite sure why this happened. The citizens of Key West decided to secede. They formed the Conch (pronounced conk) Republic. Many still fly the flag today. They demanded billions in reparations and foreign aid. The United States government ignored his wishes; but they removed the barricades.

Today Key West thrives primarily on tourism. Get there by driving the 128 miles along the Overseas Highway in the old railroad bed, or fly into the Key West Airport, or take the Key West Express ferry from Marco Island or Ft. Myers Beach. To get acquainted with the island, take the 1½ to 2 hour Conch Tour Train. Tickets can be purchased at the Flager Train station ticket office or The Old Town ticket office near Mallory Square. The guided tour goes through almost every street in Key West – a great orientation to the island. Other forms of transportation on the island are electric cars, bicycles, mopeds, taxis, and two-person bicycle strollers. Walking the streets is perhaps the best way to see the island, which is four miles long by one mile wide. Traffic can be a real challenge, especially along US 1, which has its terminus at mile 0.

Looking for action? Duval Street is your goal. Stop in and grab a beer at Hemingway’s watering hole, Sloppy Joe’s Bar and Restaurant (the original bar is half a block away at Capt. Tony’s Saloon). If your interests lean toward Jimmy Buffet, head to Margaritaville, just four blocks down the street. Up and down, the restaurants, bars, souvenir shops, and people watching Duval draw everyone to the narrow sidewalks. You might even come across one of Key West’s famous chickens strolling down the street.

Other highlights include the Hemingway house, with guided tours that are $12.00 right now. The views from the outside are free. Across Whitehead Street is the old lighthouse and keepers’ quarters. The lighthouse was moved inland to protect it from hurricanes. A couple of blocks down is the Truman White House. President Truman used this resident and the many outbuildings on it during his time in office. Other dignitaries also followed his lead: John F. Kennedy, Jimmy Carter, Bill Clinton, and Colin Powell. Speaking of President Truman, the Margaret Truman Laundromat is not to be missed. It is rumored to be named after Margaret Truman, the president’s daughter. Its location is at the corner of Margaret and Truman streets. That’s what it’s called.

Along Truman Street is the Nuestra Señora del Mar convent. Many survivors of the 1935 hurricane were treated there. The nuns erected a grotto next to the church in honor of Our Lady of Lourdes. As hurricane season approaches, many candles are lit in the grotto as a prayer to keep Key West free and safe. A marker designates the southernmost point of the continental US. Tourists love to have their photo taken.

We had lunch at Pepe’s Restaurant on Caroline Street, near Flager Station. Established in 1909, this restaurant offers hearty American fare. I had a really hard time finishing my open-faced meatloaf sandwich.

A trip to Key West is about enjoying the many water sports: parasailing, jet skiing, snorkeling, glass bottom boat rides, deep sea fishing or just relaxing on the beaches on the Atlantic Ocean side. A day trip to Dry Tortugas National Park (Fort Jefferson) leaves daily from Key West.

Above all, the people-watching, weather, and laid-back atmosphere draw people, young and old, to Conch Republic. He calls you too.

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