The history of Key West begins thousands of years prior to recorded European contact, when the island became largely occupied by the Calusa and Tequesta Native American tribes. By the end of the Age of Discovery, Key West's indigenous history had largely diminished; brief settlements by transient Seminoles in the late 18th century introduced temporary trade in the surrounding Florida Keys, with early fishing and wrecking revenues becoming lucrative among passing Natives in the region. The island's first documented exploration by Europeans occurred in 1513 by the Spanish explorer Juan Ponce de León while attempting to reach Florida's Gulf Coast.In 1513, Ponce de Leon and his fleet of three ships and 200 men set sail from Puerto Rico and discovered the land of Florida in which he named La Florida. Upon encountering the Gulf Stream, Leon and his fleet began their voyage north to discover Florida's west coast. To do so, the fleet traveled south around the Florida Keys, where he named the newly discovered islands, Los Martires ("The Martyrs"). See Weddle (1985), p. 42Weddle (1985), p 42 The island soon adopted the Spanish name, Cayo Hueso, literally meaning "bone cay", referring to the scattered bones attributed to inter‑tribal warring among Indigenous inhabitants.Key West's original name, Cayo Hueso, Spanish for "Bone Cay" or "Bone Key", refers to the white-bleached bones found on the island's beaches. It was believed to be left behind from a massacre between rivaling Natives.Viele (2013), p. 1 Although ownership was claimed by the Spanish explorers, no permanent settlement had been established, and possession of the island was briefly asserted by the British Empire in 1763.Wilkinson (n.d.), para. 1–3
Following Spain's cession of Florida to the United States in 1819, the first permanent colonization of Key West began with American possession in 1821.Homan, Reily (2000), p. 7 Legal claim of the island occurred with the purchase by businessman John W. Simonton in 1822, in which federal property was asserted only three months later with the arrival of US Navy Lieutenant Matthew C. Perry. After being designated as an official Port of Entry in 1828, Key West's wrecking industry became a significant factor in the island's growing economy. By the 1830s, Key West was the wealthiest city in the United States per capita.Florida's Writer's Project (1939), p. 332
Shortly after Florida's secession from the United States in 1861, Federal forces seized Fort Zachary Taylor, securing their position in Key West as a stronghold for the duration of the ensuing American Civil War.Wilkinson (n.d.) & para. 7 The East Gulf Blockade Squadron, established on the island by the Union navy to restrict supplies reaching Confederate ports, played a significant role in supporting Union blockade operations in the Gulf of Mexico during the conflict with the South.Key West Bicentennial (2022), p. 10 With the completion of Henry Flagler's Overseas Railroad in the early 1910s, Key West was connected to the Florida mainland with Flagler's extension of the Florida East Coast Railway (FEC).Wilkinson (n.d.). para 10 In the years prior to the Cuban Revolution in 1953, frequent transport closely linked Key West and Havana. During the Cuban Missile Crisis, the island later became a strategic position for installation of missile defense systems and military personnel in the event of a sudden attack from Cuba. In his speeches regarding Fidel Castro, President John F. Kennedy often used the phrase "90 miles from Cuba" in reference to Key West's close proximity to Cuba.
Authors Lynn M. Homan and Thomas Reilly defined Key West's role in the 20th century as that of a significant "artistic haven".Homan, Riley (2000), p. 9 The island was home to novelist Ernest Hemingway for eight years, during which he wrote several of his major works. It also served as a longtime residence for playwright Tennessee Williams, who spent much of his later life on the island. In subsequent decades, Key West hosted a number of prominent writers, including John Hersey, Wallace Stevens, Robert Frost, Elizabeth Bishop, Shel Silverstein, and Thomas McGuane, as well as various musicians and celebrities such as Jimmy Buffett, Jerry Jeff Walker, Richard Burton, and Sally Rand.
Prehistory and settlement Geological development According to USGS geologists, Barbara Lidz and Eugene Shinn, the geological history of Key West coincides with the early sedimentary development of the Florida Keys in the latter part of the Pleistocene and Holocene epochs in the last 500 million years.Shinn, Lidz (2018), pp 5–20 Early deposition resulted in the accumulation of Pleistocene limestone over 200 feet in width in the Lower Keys. Key West and the Lower Keys are categorized geologically by their particular coralloid composition, sometimes classified as the High Coral Keys, Low Coral Keys and the Oolite Keys for their early foundation of sandbars and ooid composition.Wilkinson, para 5 Key West is geologically distinctive from the rest of the Keys due to nonlinear orientation westward compared with the Upper Keys and Middle Keys, often attributed to the influence of southward or westward-trending currents. While largely formed from shallow sandbars and oolite shoals, evidence that Key West existed as a dense and inhabited "coral forest" reaching height of 10 to 18 feet is distinguishable from the "Low Coral Keys" with coral heights from five to ten feet.
During this period of geological formation, Key West's foundation was composed of compacted oolite deposits of calcium carbonate laying above Miami Colite limestone.Wilkinson, para 6–10 The reduction of sea levels from the formation of glaciers during the Ice age resulted in the collapse of Key West's early coral forests. Geological shifts in the Pleistocene Epoch, 2–3 million years ago, may have altered the island into the shallow sand cays as it would be known as by human settlers. These shoals were shallow enough to facilitate photosynthesis and the development of coral reefs.Shinn, Litz (2018), pp. 20–29 As sea levels continuously lowered during the following periods of geological formation, the Florida Keys was eventually disconnected from the Florida mainland following its exposure as a landmass 100,000 to 125,000 years ago. During this time, Key West saw significantly less coral reef development than the Upper Keys as a result of the region's nutrient rich exchange of waters through perpendicular channels from the Gulf of Mexico to the Atlantic.Wilkinson, para 10–14
Human settlement Historian John Viele traces possible human occupation of Key West to 3000 B.C.E,Viele (1996), 3 with indigenous groups related to Calusas, Matecumbes, Tequestas, and late Seminoles possibly settling in more than 800 islands in the Florida Keys. According to contemporary historian Jerry Wilkinson, the dominant inhabitants of the Florida Keys were likely the Calusa, however, the discovery of pottery fragments later indicated the presence of Tequesta and possibly evidence for Caribbean Island Natives.Wilkinson (n.d.) para 1–5 Wilkinson posits further archeological evidence indicating that the Calusa occupants may have functioned as a confederation composed of smaller tribes such as the Tequesta, Ais, or Jeaga.Wilkinson (n.d.) para 5 Primarily hunter-gatherers, the island's abundant source of fish, turtle, [obster, shellfish, and manatees provided native settlers with copious staple foods and even the installation of temporary trade outposts by later Seminoles.Viele (1996), 4 Spanish documents record a "Chief of the Key Bones", referring to a possible tribal leader or early chiefdom on Key West. During the period of Spanish control, many of Key West's native groups adopted aspects of the Spanish language, customs, and surnames, with evidence of the use of Spanish titles such as "captain-gener-al" "bishop", and "king" by Native leaders.Viele (1996), 6Upon sighting Key West during his voyage south along the keys in 1513, Ponce de León and his Spanish fleet adopted the island's original name of Cayo Hueso (). The initial discovery of dried human bones reported along the island's beaches generally align with modern interpretations to be remnants of several battles fought between rivaling tribes and subsequently used as communal graveyard.Homan, Reily (2000), 7 In his correspondence with the lawyer and politician John Rodman in the 1830s, the then Collector of Customs and surveyor in Key West, William A. Whitehead, describes an early account of intermittent occupation of the island by various feuding "aborigines of the country.", p. 62 On the presence of Natives, Whitehead notes evidence of fortifications, possible burial grounds, and human bones initially believed to be rocks. An account relayed by a resident of 50 years describes how, approximately 130 years prior, two distinct Native American tribes, the island inhabitants and those from the mainland, came into conflict: Upon discovery, Ponce de León soon claimed the island on behalf of Spain, with possible evidence of trade between Spanish vessels and Key West natives appears throughout the 17th century during Spanish colonization. However, Key West was considered to be of little value to the Spanish Empire, and with the exchange of Florida control from Spain to the Kingdom of Great Britain in 1763, the island fell under English possession. Two explanations have been offered for the origin of the name. Although there is no authentic records of the origin of the name Key West, possible anglicization during British authority likely altered the name of Cayo Hueso ("Bone Cay") to a modified Key West in following years.Key West may be an anglicized version of the Spanish Cayo Hueso. Another suggests that it derives from the island's position as the westernmost of the chain of islands—or keys—extending from the Florida mainland, hence the name "Key West."Browne (1912), p. 8 The island's initial surveyor William Whitehead accepted the former theory, saying in a letter: "...hence the name of the island, Cayo Hueso, which the English, with the same facility which enabled them to transform the name of the wine Xeres Seco into 'Sherry Sack,' corrupted into Key West."
With the onset of British control of Florida, Key West became mostly uninhabited, with neither the arriving British nor Spanish exercising de facto control.Viele (1996), 7 In 1766, Major general and East Florida governor, James Grant, proposed the idea of establishing a military base on Key West to further regulate any activity in its surrounding waters. Grant often urged that a post or settlement on Key West would be ideally situated for trade with Havana and have a strategic advantage point in the case of a war with Cuba, but nothing came of his plea. After observing fleets of about 30 Cuban and 14 Bahamian fishing vessels in the Florida Keys, Grant became insistent on preventing the intrusion of foreign vessels, as he feared their presence could threaten British control of Florida.Viele (1996), 13 Grant consisted of no means to prevent the situation.In 1763, control of Florida was traded with the British for Spanish authority over Havana. While British officials, including Grant, saw Key West's value for trade in the Florida Straits, the Spanish saw limited use for the island.McRae (1923), 135