Key West is an island located in the Straits of Florida and is about 4 miles long and 1 mile wide, with a total land area of 4.2 square miles. The average elevation above sea level is about 8 feet and the maximum elevation is about 18 feet, within a 1-acre area known as Solares Hill.

The city of Key West is the southernmost city in the contiguous United States and the island is the westernmost island connected by the Overseas Highway in the Florida Keys. The city boundaries include the island of Key West and Stock, Sigsbee Park—originally known as Dredgers Key, Fleming Key and Sunset Key (the latter two are part of the Naval Air Station and are inaccessible to the general public.

Key West and most of the Florida Keys are on the dividing line between the Atlantic Ocean and the Gulf of Mexico. The two bodies have different currents, with the calmer and warmer Gulf of Mexico being characterized by great clumps of seagrass. The area where the two bodies merge between Key West and Cuba is called the Straits of Florida.


Precolonial and colonial times

The last Native American residents of Key West were Calusa refugees who were taken to Cuba when Florida was transferred from Spain to Great Britain in 1763.  Cayo Hueso is the original Spanish name for the island of Key West. It literally means “bone cay”, cay referring to a low island or reef. It is said that the island was littered with the remains (bones) of prior native inhabitants, who used the isle as a communal graveyard.

In 1766 the British governor of East Florida recommended that a post be set up on Key West to improve control of the area, but no nation exercised de facto control. There are rumors of permanent settlements in the Keys but the locations are not known.  Fishermen from New England started visiting the Keys after the end of the War of 1812, and may have briefly settled on Key Vaca.

In 1815, the Spanish Governor of Havana, Cuba deeded the island of Key West to Juan Pablo Salas, an officer of the Royal Spanish Navy Artillery posted in Saint Augustine, Florida. And in 1821, the United States took possession of Florida from Spain, there were few permanent inhabitants anywhere in the Florida Keys. Salas was so eager to sell the island that he sold it twice – first for a sloop valued at $575 to a General Geddes, a former governor of South Carolina, and then to a U.S. businessman John W. Simonton for the equivalent of $2,000 in pesos in 1821. The island was considered the “Gibraltar of the West” because of its strategic location on the 90-mile wide deep shipping lane in the Straits of Florida, between the Atlantic Ocean and the Gulf of Mexico.  Cubans and Bahamians regularly visited the Keys, the Cubans primarily to fish, while the Bahamians fished, caught turtles, cut hardwood timber, and salvaged wrecks. Smugglers and Pirates also used the Keys for concealment.

On March 25, 1822, Lt. Commander Perry sailed to Key West and planted the U.S. flag, claiming the Keys as United States property later renamed Cayo Hueso (Key West) to Thompson’s Island. In 1823, U.S. Navy Commodore David Porter of the Indies Anti-Pirate Squadron took charge of Key West, which he ruled as military dictator under martial law countering piracy and the slave trade in the Key West area.

First developers

Soon after his purchase, John Simonton subdivided the island into plots and sold three undivided quarters of each plot. Simonton spent the winter in Key West and the summer in Washington, where he lobbied hard for the development of the island and to establish a naval base on the island, both to take advantage of the island’s strategic location and to bring law and order to the town.

In 1852 the first Catholic Church was built and became a landmark when five Sisters arrived from Montreal, Canada, and established the first Catholic school in South Florida and is still operating today as Mary Immaculate Star of the Sea School.

American Civil War and late 19th century

Fort Zachary Taylor, active during the Civil War, contains the largest collection of Civil War cannons. During the American Civil War, while Florida seceded and joined the Confederate States of America, Key West remained in U.S. Union hands because of the naval base.

By1861, Key West was a major center of U.S. salt production, harvesting the commodity from the sea (via receding tidal pools) rather than from salt mines. The industry was destroyed by an 1876 hurricane and never recovered.

During an unsuccessful Cuban war for independence in the 1860s – 1870s, many Cubans sought refuge in Key West.  A major fire in 1886 spread out of control, destroying 18 cigar factories and 614 houses and government warehouses. By 1889, Key West was one of the largest and wealthiest city in Florida.  The USS Maine sailed from Key West on her fateful visit to Havana, where she blew up and sank in Havana Harbor, igniting the Spanish–American War.

20th century

The railway yard and station on Trumbo Point in Key West circa 1930

was connected to the Florida mainland via the Overseas Railway extension of Henry M. Flagler’s Florida East Coast Railway (FEC).  The Labor Day Hurricane of 1935 destroyed much of the railroad and killed hundreds of residents. The FEC could not afford to restore the railroad.

The U.S. government then rebuilt the rail route as an automobile highway built atop many of the footings of the railroad. It became an extension of U.S. Route 1 called the Overseas Highway which remains today.

Pan American Airlines was founded in Key West, originally to fly visitors to Havana, in 1926. The airline contracted with the United States Postal Service to deliver mail to and from Cuba and the United States. Prior to the Cuban revolution of 1959, there were regular ferry and airplane services between Key West and Havana.

In the late 1950s, many of the large salt ponds on the eastern side of the island were filled in and is called New Town, which contains shopping centers, retail malls, residential areas, schools, ball parks, and Key West International Airport.   John F. Kennedy used Key West’s “90 miles from Cuba” extensively in his speeches against Fidel Castro during the Cuban Missile Crisis (a U.S. Naval Blockade of Russian missles via shipments to Communist Cuba) which brought the U.S. on the brink of possible Nuclear War.

In 1982, Key West asserted independence as the Conch Republic as a protest over a United States Border Patrol blockade in response to the Mariel Boatlift of Cuban Refugees. The Border Patrol also stopped every car leaving the Keys, supposedly searching for illegal immigrants attempting to enter the mainland United States. This paralyzed the Florida Keys Tourism.  Flags, T-shirts and other merchandise representing the Conch Republic are still popular souvenirs for visitors to Key West, and Independence Celebration is celebrated annually on April 23.

Old Town

The earliest Key West neighborhoods, is on the western part of the island. The Key West Historic District includes Mallory Square, Duval Street, the Truman Annex (President Trumans Summer White House)  and Fort Zachary Taylor. Old Town is where the classic bungalows and guest mansions are found. Bahama Village, southwest of Whitehead Street, features houses, churches, and sites related to its Afro-Bahamian history. The Meadows, lying northeast of the White Street Gallery District, is exclusively residential.

Generally, the structures date from 1886 to 1912. The basic features that distinguish the local architecture include wood-frame construction of structures set on foundation piers about three feet above the ground due to historical flooding during Tropical Storms/ Hurricanes. Exterior characteristics of the buildings are peaked metal roofs, horizontal wood siding, gingerbread trim, pastel shades of paint, side-hinged louvered shutters, covered porches (verandas) along the fronts of the structures..

Among the Oldest structures include Cussans-Watlington House 1836 and the John Huling Geiger House 1849, now preserved as the Audubon House and Tropical Gardens. Fortifications such as Fort Zachary Taylor, the East Martello Tower, and the West Martello Tower, helped ensure that Key West would remain in Union control throughout the Civil War. Another landmark built by the federal government is the Key West Lighthouse, now a museum.

Two of the most notable buildings in Old Town, occupied by prominent twentieth-century residents, are the Ernest Hemingway House and the Harry S. Truman Little White House. Additionally, the residences of some historical Key West families are recognized on the National Register of Historic Places including the Porter House and the Gato House. Old Town includes the Key West Cemetery, founded in 1847, containing above-ground tombs, notable epitaphs, and a plot where some of the dead from the 1898 explosion of the USS Maine are buried.

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