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Key West: History and things to do
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Key West - History and things to do

Key West is the southernmost city in the continental U.S. and is the southern terminus of U.S. Route 1. It is 129 miles southwest of Miami and 98 miles north of Cuba. Juan Ponce de Leon was the first European visitor in 1521. The island was purchased by John W. Simonton in 1821 from the Spanish based on a recommendation of John Whitehead, due to the island’s strategic location. The island was considered the “Gibraltar of the West” because of its location on the shipping lane Straits of Florida which connects the Atlantic Ocean with the Gulf of Mexico.

During the civil war, Florida joined the Confederate States of America, but Key West remained in U.S. Union hands. Between 1845 and 1866 Fort Zachary Taylor was constructed on the island. Fort Jefferson in the Dry Tortugas, 68 miles to the west, served as a prison for Dr. Samuel Mudd, the doctor who set the broken leg of John Wilkes Booth, the assassin of President Abraham Lincoln.

Henry M. Flagler connected Key West with the mainland by constructing the Overseas Railroad in 1912. This railroad was destroyed in 1935 by a hurricane, but was rebuilt by the U.S. government in 1938 as a roadway extending of U.S. Highway 1 to Key West.

President Truman stayed in Key West for 175 days of his presidency. Ernest Hemingway wrote or worked on “A Farewell to Arms”, “Death in the Afternoon”, “For Whom the Bell Tolls”, “The Snows of Kilimanjaro”, and “The Short Life of Francis Macomber” while in Key West. Tennessee Williams wrote his first draft of “A Street Car Named Desire” while in Key West and listed Key West as his primary residence until his death in 1983.

In 1982 Key West declared its “independence” as the Conch Republic in protest over a U.S. Border Patrol blockade that was a response to the Mariel Boatlift from Cuba. You can still buy Conch Republic souvenirs on Duval Street.

Old Town, on the west side of the island, is the main tourist destination. Most structures date from 1886 to 1912 and have a distinctive architecture. New Town, the east end of the island, is built on a landfill and contains shopping centers, strip malls, and the airport.

The following are some of the sights to visit during your stay in Key West:

  • Mallory Square and the Sunset Festival. Every night about two hours before sunset the local street vendors and performers start to assemble at Mallory Square on the northwest corner of the island. See the performing cats, jugglers, tight rope walkers, and escape artists prior to the nightly plunge of the sun into the Gulf of Mexico. This is a must see event!
  • Touring Duval Street. Duval Street, the main drag of old town Key West, is ~15 blocks long and contains shops, art galleries, bars, and restaurants including Fast Buck Freddie’s (a tropical department store) and Sloppy Joes (Ernest Hemingway’s favorite bar). At its northern most end is Mallory Square and near its southern end is the Southernmost Point (a few block to the west) with its huge red and yellow concrete buoy and Cuba (a mere 98 miles to the south).
  • Key West Lighthouse. The lighthouse once guided ships past the dangerous reefs around Key West. Now you can climb the 88 steps to the top for a great view of the surroundings and tour the Keeper’s Quarters which contains lighthouse artifacts and the maritime history of the Keys.
  • Ernest Hemingway’s House. Hemingway lived in Key West for 11 years and wrote many of his best novels in his studio over the garage. The house and studio contain his manual typewriter, numerous artifacts, and over 40 of the descendants of his 6 (and 7) toed polydactyl cats!
  • Historic Zero Mile Marker and Southernmost Point. Locate and visit the historic zero (0) mile marker that marks the end of U.S. Highway 1 and the large marker of the southernmost point in the U.S.
  • Mel Fisher Maritime Heritage Museum. See some of the $450,000,000 treasure recovered by Mel Fisher of the Nuestra Senora de Atocha and the Santa Margarita, the Spanish galleons that sank during a hurricane on September 6, 1622, near Key West, Florida. The treasure included over 40 tons of silver and gold, 100,000 Spanish “Pieces of Eight” coins, gold doubloons, emeralds, and other artifacts.
  • Old Town Trolley Tours and the Couch Tour Train. Two tours that take you to the various sights of Key West. The trolley allows you to get off and board a later tour while the Train is one continuous tour. These are a good way to get oriented to Key West and its various sights.
  • Key West Aquarium. A small aquarium in the Mallory Square area that contains a touch tank, tarpon, sharks, and many other fish.
  • Key West Cemetery. Take a self guided tour through the cemetery to see the above ground vaults and tombs, Robert’s “I told you I was sick” headstone, “At least I know where he’s sleeping tonight” tombstone, military memorials, vampire vaults, and an unidentified tombstone (a tree completely surrounds it).
  • Ft. Jefferson /Dry Tortugas National Park. The least visited National Park in the U.S. because of its location (68 miles west of Key West). Half and full day tour trips are available by plane, boat, and ferry of this 19th century coastal fort. Tour the fort, bird watch, snorkel, and sun bathe at this unique location.
  • Audubon’s House and Tropical Gardens. Visit the house where it is believed Audubon created 18 drawing for his “Birds of America” folio during a visit in 1932. The house contains 28 first-edition Audubon works.
  • Truman’s Little White House. President Harry S. Truman retreated to Key West at his doctor’s suggestion to recover from bronchial pneumonia, staying 175 days of this presidency. The tour provides a glimpse of American History having housed Presidents Truman, Eisenhower, and Carter, Thomas Edison, and many world dignitaries.
  • Fort Zachary Taylor State Historical Site. This site is entered through the Truman Annex on Southard Street. It was built between 1845 and 1866, remained in Union hands throughout the Civil War, used during the Spanish-American War, and contains the largest collection of Civil War cannons.
  • Key West Heritage House Museum & Robert Frost Cottage. See 200 years of Key West culture through the lives of the Porter family, who have lived on the island for seven generations. The family’s literary connections/guests included Robert Frost, Tennessee Williams, Thornton Wilder, Gloria Swanson, Sally Rand, and others.
  • Curry Mansion. An elaborate Victorian house built on the site of the homestead of Florida’s first millionaire. This historical house showcases an era of elegance.
  • Nancy’s Secret Garden. A little known one-acre rain forest garden on Free School Lane that includes over 100 palm trees, aroids, cycads, and orchids.
  • Ghost Tours of Key West. Take a 90 minute walking tour through Old Town’s historical haunted lanes each night and 8 and 9 p.m. from the Crowne Plaza La Concha Hotel at 430 Duval St.
  • Key West Ship Wrecker’s Historeum Museum. Take a walk through the past when the industry of ship wrecking was alive and strong in Key West.
  • Alternative trips include fishing trips, snorkel and scuba dives at the surrounding reefs, and sunset sailing trips.
This website is maintained by Doug Dankel.
Page updated on 30-Apr-2007