Key West (Spanish: Cayo Hueso [kaʝo ˈweso]) is a coral cay island in the Straits of Florida, at the southernmost end of the U.S. state of Florida and its outlying Florida Keys archipelago. Together with all or parts of the separate islands of Dredgers Key, Fleming Key, Sunset Key, and the northern part of Stock Island, it constitutes the City of Key West.

For thousands of years, Key West and the surrounding islands were inhabited by various Native American tribes. The island's first recorded European contact occurred in 1513, when an expedition led by Spanish conquistador Juan Ponce de León circumnavigated the Florida Keys amid his voyage along the coast of Florida, though no permanent settlement was established. Over the following centuries, the island remained sparsely populated while passing between periods of Spanish and British control. Following the transfer of Florida to the United States in 1819, Key West rapidly developed into a major maritime center, with its strategic location along the Florida Straits and thriving wrecking industry helping make it one of the wealthiest communities in the United States during the 19th century.

Key West is the southernmost city in the contiguous United States and the westernmost island in the Florida Keys connected by highway, located about 130 miles (210 km) southwest of Miami and roughly 95 miles (153 km) north of Cuba. The island measures approximately 4 miles (6 km) long and 1 mile (2 km) wide, with a total land area of about 4.2 square miles (11 km²), and the city itself spans roughly 5.6 square miles (14.5 km²). It serves as the county seat of Monroe County, which includes a majority of the Florida Keys and part of the Everglades, and had a population of 26,444 at the 2020 census, carrying the motto “One Human Family.”

Key West functions as a major transportation and tourism hub, serving as the southern terminus of U.S. Route 1 and hosting a passenger cruise port, an international airport, and Naval Air Station Key West. Its main commercial corridor is Duval Street, which runs from the Gulf of Mexico to the Atlantic Ocean. Key West lies within the Florida Keys National Marine Sanctuary and is located near several protected areas, including the Dry Tortugas National Park and the Key West National Wildlife Refuge; due to its proximity to the Great Florida Reef, the island serves as a notable center for recreational diving.

History

Precolonial and colonial times At various times before the 19th century, people who were related or subject to the Calusa and the Tequesta inhabited Key West. 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., pp. 62–63 This island was the westernmost Key with a reliable supply of water.Windhorn, Stan & Langley, Wright 1973. Yesterday's Key West Between 1763, when the Kingdom of Great Britain took control of Florida from Spain, and 1821, there were few or no permanent inhabitants anywhere in the Florida Keys. 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 privateers also used the Keys for concealment.

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 nothing came of it. During both the British and Spanish periods no nation exercised de facto control. The Bahamians apparently set up camps in the Keys that were occupied for months at a time, and there were rumors of permanent settlements in the Keys by 1806 or 1807, 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 1818.

Ownership claims

In 1815, the Spanish governor of Cuba in Havana deeded the island of Key West to Juan Pablo Salas, an officer of the Royal Spanish Navy Artillery posted in Saint Augustine, Florida. After Florida was transferred to the United States in 1821, Salas was so eager to sell the island that he sold it twice – first for a sloop valued at $575 to a General John Geddes, a former governor of South Carolina, and then to a U.S. businessman John W. Simonton, during a meeting in a Havana café on January 19, 1822, for the equivalent of $2,000 in pesos in 1821.

Geddes tried in vain to secure his rights to the property before Simonton who, with the aid of some influential friends in Washington, was able to gain clear title to the island. Simonton had wide-ranging business interests in Mobile, Alabama. He bought the island because a friend, John Whitehead, had drawn his attention to the opportunities presented by the island's strategic location. John Whitehead had been stranded in Key West after a shipwreck in 1819 and he had been impressed by the potential offered by the deep harbor of the island. The island was indeed considered the "Gibraltar of the West" because of its strategic location on the –wide deep shipping lane, the Straits of Florida, between the Atlantic Ocean and the Gulf of Mexico.

On March 25, 1822, Lt. Commander Matthew C. Perry sailed the schooner to Key West and planted the U.S. flag, claiming the Keys as United States property. No protests were made over the American claim on Key West, so the Florida Keys became the de facto property of the United States. After claiming the Florida Keys for the United States, Perry renamed Cayo Hueso (Key West) to Thompson's Island for Secretary of the Navy Smith Thompson, and the harbor Port Rodgers in honor of War of 1812 hero and President of the Navy Supervisors Board John Rodgers. In 1823, Commodore David Porter of the United States Navy West Indies Anti-Pirate Squadron took charge of Key West, which he ruled as military dictator under martial law. The United States Navy gave Porter the mission of countering piracy and the slave trade in the Key West area.

Early development Following the purchase of Key West by John W. Simonton in 1821, the island was subdivided and sold to a small group of investors who became known as its early “founding fathers,” including John Whitehead, John Fleeming, and Pardon C. Greene. Greene was the only one to permanently settle on the island, where he became a prominent merchant, city council member, and briefly served as mayor before his death in 1838. Whitehead, who had originally encouraged Simonton’s purchase, lived on the island intermittently and later left permanently in 1832, while Fleming remained only briefly before departing for Massachusetts. The island’s early development was further shaped by Simonton’s lobbying efforts in Washington, D.C., wherein he promoted Key West’s strategic maritime value and advocated for the establishment of a naval base.

In 1829, the island was formally platted by William Adee Whitehead. During this period, Key West expanded rapidly as maritime trade, wrecking, and shipping industries grew, supported by its designation as a U.S. port of entry and the establishment of local courts and governance structures. By the 1830s, Key West had become the wealthiest city per capita in the United States, driven by its strategic location along major shipping lanes and the expansion of salvage-based commerce. Throughout the 1840s, Key West was repeatedly impacted by severe hurricanes, including the devastating 1846 Havana hurricane, which caused widespread destruction across the island. However, religious and educational development continued to advance, marked by the construction of St. Mary’s Star of the Sea Catholic Church in 1852 and the establishment of the first Catholic school in South Florida in 1864, founded by the Sisters of the Holy Names of Jesus and Mary. The school is still operating today and is now known as the Basilica School of Saint Mary Star of the Sea. By the mid-19th century, Key West had emerged as both a wealthy maritime hub and a strategically significant settlement in the southeastern United States. American Civil War and late 19th century

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. Most locals were sympathetic to the Confederacy, however, and many flew Confederate flags over their homes.A Chronological History of Key West A Tropical Island City, Stephen Nichols, 3rd ed. However, Key West was also home to a large free black population. This population grew during the war as more enslaved black people fled from their enslavers and came under the relative safety of the Union garrison there. Fort Zachary Taylor, constructed from 1845 to 1866, was an important Key West outpost during the Civil War. Construction began in 1861 on two other forts, East and West Martello Towers, which served as side armories and batteries for the larger fort. When completed, they were connected to Fort Taylor by railroad tracks for movement of munitions. Early in 1864, 900 men from the 2nd United States Colored Troops (USCT) arrived in Key West as replacements for the 47th Pennsylvania Volunteers. Many of these men would see action in southern Florida and the 2nd USCT would become "one of the most active" black regiments in Florida.Solomon & Erhart (1999), 336 Fort Jefferson, located about from Key West on Garden Key in the Dry Tortugas, served after the Civil War as the prison for Samuel A. Mudd, convicted of conspiracy for setting the broken leg of John Wilkes Booth, the assassin of President Abraham Lincoln.

In the 19th century, major industries included wrecking, fishing, turtling, and salt manufacturing.June Keith, June Keith's Key West & The Florida Keys: A Guide to the Coral Islands (5th ed.: Palm Island Press, 2014), p. 8. From 1830 to 1861, 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. After the outbreak of the Civil War, Union troops shut down the salt industry after Confederate sympathizers smuggled the product into the South. Salt production resumed at the end of the war, but the industry was destroyed by an 1876 hurricane and never recovered, in part because of new salt mines on the mainland.

During the Ten Years' War (an unsuccessful Cuban war for independence in the 1860s and 1870s), many Cubans sought refuge in Key West. Several cigar factories relocated to the city from Cuba, and Key West quickly became a major producer of cigars. The Great Fire of Key West, on April 1, 1886, started at a coffee shop next to the San Carlos Institute and spread out of control, destroyed 18 cigar factories and 614 houses and government warehouses. Some factory owners chose not to rebuild and instead moved their operations to the new community of Ybor City in Tampa, leading to a slow decline in the cigar industry in Key West. Still, Key West remained the largest and wealthiest city in Florida at the end of the 1880s.

sailed from Key West on her fateful visit to Havana, where she blew up and sank in Havana Harbor, igniting the Spanish–American War. Crewmen from the ship are buried in Key West, and the Navy investigation into the blast occurred at the Key West Customs House.

20th century