The Port of Key West is the seat of Monroe County and the southernmost city in the Continental United States. The Port of Key West is 151 nautical miles (210 kilometers or 130 miles by air) southwest of Miami. By comparison, it is only 87 nautical miles (167 kilometers or 104 miles by air) east-northeast of Havana, Cuba.

The Port of Key West is a popular destination for cruise ships and a well-known vacation spot. Because of its favorable weather, the Naval Air Station Key West is an important training station for naval aviation. The Port of Key West was President Harry Truman's winter White House. The 2000 US Census reported a population of over 25 thousand in the Port of Key West.

Before Europeans arrived in the New World, the Calusa people inhabited what would become the Port of Key West. In 1521, Juan Ponce de Leon arrived at Key West, laying claim to the island for Spain.

The island was called Cayo Hueso by the Spaniards due to the many bleached bones found there. Apparently, earlier inhabitants had used the island as a communal graveyard. Spanish-speaking people still call the Port of Key West Cayo Hueso, and the name is used frequently by local businesses.

When England took over the Florida territory in 1763, they moved local Spaniards and indigenous peoples living in the Port of Key West to Havana. Twenty years later when Spain re-won Florida, they did not resettle the island. Fishermen from Cuba and the British Bahamas used the island. When the United States won independence, American fishermen also frequented the Port of Key West. Even though Spain claimed ownership of Key West, no country prevailed for many years.

The Spanish governor of Cuba gave the Port of Key West to Juan Pablo Salas in 1815. When the United States gained control of Florida, Salas sold his island twice. First, he traded Key West for a sloop, and then he sold it to businessman John W. Simonton. The sloop salesman immediately sold the Port of Key West to General John Geddes who had been the governor of South Carolina; however, Simonton was able to use his influence in Washington to get a clear title to the island.

The island of the Port of Key West was valuable due to its strategic location on the Straits of Florida, the busy shipping lane between the Gulf of Mexico and the Atlantic Ocean. In 1822, Commodore Matthew Perry claimed the Florida Keys for the United States. He renamed Cayo Hueso as Thompson's Island after the Secretary of the Navy. He named the harbor Port Rodgers, honoring John Rodgers, a hero in the War of 1812.

In 1823, the US Navy's West Indies Anti-Pirate Squadron took charge of the Port of Key West. His tenure was marked by claims that he ruled more like a military dictator.

The Port of Key West cites four men as early developers of the island. John Simonton, who had bought the island from Juan Salas, spent his winters in the Port of Key West. During the summer, he lived in Washington, and he lobbied for island development and for the establishment of a naval base there.

The only founding father to live on the island permanently was Pardon C. Greene who was the mayor of the town briefly. He also founded the successful P.C. Greene and Company. Living there for just eight years, John Whitehead was a partner in P.C. Greene and Company while he lived in the Port of Key West. Leaving the island in 1832, he returned only once in 1861 during the American Civil War.

Englishman John W.C. Fleeming was a successful merchant in Mobile, Alabama, when he became friends with John Simonton. Fleeming lived in the Port of Key West for a few months in 1822 and did not return until 1832. He planned on manufacturing salt on the island.

The first Catholic Church was built in the Port of Key West in 1852. In 1864, five Sisters of the Holy Names of Jesus and Mary came to the Port of Key West from Montreal to establish South Florida's first Catholic school and convent.

Many of the Port of Key West's first citizens were immigrants. The European descendents called Conchs ("conks") immigrated from the Bahamas beginning in the 1830s. British loyalists fleeing the US during the American Revolution also immigrated to the Port of Key West. Many black Bahamians also immigrated to the Port of Key West, living now in a section of Old Town called "Bahama Village." By the 20th Century, many residents of the Port of Key West called themselves Conch, even though they were not descendants of the Europeans from the Bahamas.

In the early 1800s, several important industries were active in the Port of Key West: fishing, salvage, and salt. By 1860, shipwrecks in the Florida reefs had made the Port of Key West the richest and biggest city in the State.

When Florida seceded from the United States during the Civil War, the Port of Key West was held by the Union due to the naval base located there, even though many residents were sympathetic to the South and flew Confederate flags at their homes. Fort Zachary Taylor became an important Civil War outpost. Joined by rail, the East and West Mortello Towers served as armories for the larger fort.

During Cuba's failed war for independence in the mid-1800s, many Cubans escaped to the Port of Key West. By the late 19th Century, the Port of Key West had a prosperous cigar-making industry, although its salt and salvage industries had declined. By 1889, the Port of Key West was Florida's biggest and richest city.

Until the early 20th Century, the Port of Key West was fairly isolated. In 1912, it was connected to Florida's mainland by the Overseas Railway, an extension of the Florida East Coast Railway. Unfortunately, the Labor Day Hurricane of 1935 killed many residents of the Port of Key West, including about 400 veterans of World War I, and destroyed the railroad. When private interests could not afford to rebuild the railroad, the United States government replaced it with a highway for automobiles in 1938. That highway is the terminus of US 1, the 3825 kilometer (2377 mile) road that stretches along the East Coast from Fort Kent in Maine to the Port of Key West.

Locals proudly report that Ernest Hemingway wrote his famous A Farewell to Arms while he was in the Port of Key West waiting for the delivery of an automobile. Charles Thompson, the owner of the hardware store, introduced Hemingway to deep-sea fishing, which became a major interest for the rest of his life. They say that fisherman Joe Russell was the model for Freddy in To Have and Have Not, and some parts of the original manuscript were found in Joe's bar after the writer's death.

The home at 907 Whitehead Street was a wedding present for the Hemingway's in 1931. Hemingway wrote or worked on several other novels while he lived in the Port of Key West: For Whom the Bell Tolls, The Snows of Kilimanjaro, Death in the Afternoon, and The Short Happy Life of Francis Macomber. After the Hemingways divorced in 1939, "Papa" seldom returned to the Port of Key West.

American dramatist Tennessee Williams also found the Port of Key West an inspirational place. Beginning his visits to the island in 1941, some believe that Williams wrote the first draft of A Streetcar Named Desire at the La Concha Hotel in 1947. In 1949, he made the Port of Key West his home until he died in 1983. It was the only home he ever owned, though he rented homes all over the United States. In 1956, the movie based on his The Rose Tattoo was filmed on the island.

Being closer to Havana than to Miami, the Port of Key West has a large Cuban population. The son of Carlos Manuel de Cespedes, father of the Cuban Republic, was elected mayor of the Port of Key West in 1876. Cubans operated or worked at 200 factories in the Port of Key West, producing about 100 million cigars each year.

In 1898, the US battleship USS Maine departed the Port of Key West on its way to Havana with the mission to protect American interests. Blowing up in Havana Harbor, almost 75% of the crew were killed in the explosion and were buried in the Port of Key West. Although the cause of the explosion was not clear, many in the US blamed Spain. The explosion became an important contributor to the beginning of the Spanish-American War.

In 1926, Pan American Airlines was established in the Port of Key West to fly people to Havana. Before the 1959 revolution in Cuba, air and ferry services traveled regularly between the Port of Key West and Havana. During the Mariel Boatlift in the 1980s when up to 125 thousand people were allowed to leave Cuba, the Port of Key West was overwhelmed by the refugees. In 2003, refugees hijacked a Cuban Airlines flight and flew it into the Port of Key West.

The first regularly scheduled cruise ship arrived in the Port of Key West in 1969, and it called on the Port of Key West. Between 1969 and 1984, the Port of Key West hosted 266 port calls. By 1999, almost 600 thousand passengers arrived at the Port of Key West aboard cruise ships.

To protest a US Border Patrol blockade, a response to the Mariel Boatlift, the Port of Key West declared its independence in 1982, naming itself the Conch Republic. The blockade had brought traffic to a stop, creating a 27-kilometer (17-mile) traffic jam as each car was searched for illegal immigrants. While the declaration of independence was more protest that actual political movement, residents still celebrate April 23rd with the Conch Republic Independence celebration each year.

In 1984, the City Commission authorized improvements that made the city's Mallory Dock a full-service cruise ship dock. Today, the Port of Key West has three docking facilities: the privately-owned Pier B, the Mallory Square Dock, and the Navy Mole.

Sitting on the north side of the deep-water channel that connects the Atlantic Ocean to the Gulf of Mexico, the Port of Key West has always been an important military post. It has been called the "Gibraltar of the West" since the 1820s. When World War II began, the US Navy expanded its Port of Key West operations. It expanded its property from 50 acres to 3,000 acres, used landfill to construct Fleming Key, and built a pipeline for water that extends the length of the Florida Keys. About 15 thousand military personnel and 3400 civilians were stationed at the Port of Key West base at its height. Today, the base includes three major installations: NAS Key West, the Truman Annex, and the Trumbo Annex.

NAS Key West is the most important facility. The US Navy trains pilots there. In 2006, almost five thousand military personnel (including families) and over 1300 civilians were stationed there. Located six kilometers (four miles) east of the Port of Key West's central business district, the first naval base was established in 1823 to stop piracy. The base was then expanded during the Mexican-American and Spanish-American Wars. During World War I, the base was further expanded, and a submarine base began operating there in 1917. The first Naval flight from NAS Key West was made that year. The first class of pilot trainees arrived there in 1918, and its reputation as a premiere air training station has continued since then.

In 1943 during the Second World War, German submarines were sinking Allied vessels within sight of the Port of Key West. In 1943, almost 50 ships were torpedoed off Florida's coastline, and NAS Key West became an important site for the US's defense of the Gulf of Mexico. The naval station near the Port of Key West has been used on many occasions by both active and reserve Navy, Marine Corps, Air Force Reserve, and Air National Guard fighter and rescue squadrons. Since World War II, many new units have been transferred to NAS Key West as the Department of Defense closed other bases.

Near Fort Zachary Taylor at the southwest end of the Port of Key West, the Truman Annex was used as a submarine pen and for the Fleet Sonar School. President Harry Truman used the Commandant's on-base home for his winter White House. While there are still some government offices (including the NOAA Hurricane Forecasting Center) at the location and the Navy owns the piers, much of the Truman Annex has been released to the Port of Key West and private developers.

The US Coast Guard uses the Trumbo Annex, although it was established as a base for Navy seaplanes. Later used for helicopters, it is used for military housing today. The Navy Gateway Inns & Suites (NGIS), the tallest building in the Port of Key West, is located there. Civilians cannot enter the Port of Key West's Trumbo Annex without US Navy clearance.

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