# History of Key West

Thousands of years before European discovery, the island of Key West was largely occupied by the Calusa and Tequesta Native American tribes. Brief settlements by transient Seminoles in the late 18th century introduced temporary trade in the Florida Keys; early fishing and wrecking revenues became notable among passing Natives in the region. The island's first documented discovery by Europeans occurred in 1513 by Spanish explorer Ponce de León while attempting to reach Florida's Gulf Coast. The island soon adopted the Spanish name, Cayo Hueso, literally meaning "bone cay", referring the scattered bones believed to be left behind from warring natives. 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 in 1763.
Following Spain's secession of Florida to the United States in 1819, the first permanent colonization of Key West began with American possession in 1821. 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 U.S. Navy Lieutenant Mathew 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. Shortly after Florida's secession from the United States, Union soldiers seized Fort Zachary, securing their position in Key West as a stronghold for the duration of the war. The East Gulf Blockade Squadron, established on the island by the Union Navy to limit the import of supplies to Confederate port cities along the Gulf of Mexico, was a key influence in the outcome of the American Civil War.
With the completion of Henry Flagler's Overseas Railway in the early 1910s, Key West was connected to the Florida mainland with Flagler's extension of the Florida East Coast Railway (FEC). In the years prior to the Cuban Revolution in 1953, frequent transport existed between 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.

## Prehistory and settlement
### Prehistory

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. 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. 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. 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. 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 then 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.

### Human settlement

Possible human occupation of Key West can be traced back to 3000 B.C.E, with indigenous groups related to Calusas, Matecumbes, Tequestas, and late Seminoles possibly settling in more than 800 islands in the Florida Keys. It is relatively agreed among historians that the dominant inhabitants of the Florida Keys were the Calusa, however, the discovery of pottery fragments later indicated the presence of Tequesta and possibly evidence for Caribbean Island Natives. Among archeological debates, the possible occupation by the Calusa may have existed as a confederation composed of smaller tribes such as the Tequesta, Ais, or Jeaga. Primarily hunter-gatherers, the island's abundant source of fish, turtle, lobster, shellfish, and manatees provided native settlers with copious staple foods and even the installation of temporary trade outposts by later Seminoles. 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.
Upon 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 (Spanish pronunciation:). Dried bones were discovered along the island's beaches, believed by modern historians to be remnants of several battles fought between rivaling tribes and used as communal graveyard. 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. Possible Anglicization during British authority may have altered the name of Cayo Hueso ("Bone Cay") to a butchered Key West in following years.
With the onset of British control of Florida, Key West become mostly uninhabited, with neither the arriving British nor Spanish exercising de facto control. 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, however, 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. Grant consisted of no means to prevent the situation.
For much of the 18th century, smugglers and privateers used the island to conceal valuables; Bahamians and Cubans often visited for fishing and other various forms of resource manufacture. British expansion westward in the Thirteen Colonies prompted the immigration south by many of the Creek Indian Nation in the early 1700s. These migrants, who settled much in Florida, came as far as Key West in 1770. Raids by outside natives in the early 1700s, supported and sometimes led by the British, resulted in the destruction of several Spanish missions in Florida. As a result, many of the remaining natives of Key West fled to Cuba. The 1750s and 1760s saw the last Native American residents of Key West, when roughly eighty families of Calusa natives reportedly taking refuge on the island in 1763.

## 19th century

   A Salute of 17 Guns is to be find at 8 o'clock this morning from the Battery in front of the Town, and the American Ensign is to be hoisted at the Flag Staff.
   The Town is hereafter to be called Allenton, and the Battery, Thompsons Battery.
During the early 19th century, with neither Spain nor Britain maintaining effective authority over Key West, residents of Havana continued to issue fishing licenses to vessels in the British territory. On 26 August 1815, the Royal Spanish Navy Artillery officer, Juan Pablo Salas, acquired a Spanish land grant of Key West from Juan José de Estrada, the 7th governor of Spanish East Florida, for his "meritorious service to the King of Spain". Six years later on December 21, 1821, the American businessman from Mobile, Alabama, John W. Simonton offered to purchase Sala's land grant for $2,000. Intrigued by the island's deep water ports and access to wide shipping lanes, Simonton conducted the purchase with Salas while meeting in Havana following Spain's formal cession of Florida to the United States in 1821. Eager to sell the island, Salas had initially sold Key West for a total of $575 to a former governor of South Carolina, General John Geddes, who was unable to secure the rights before Simonton, assisted by influential friends from Washington D.C., asserted legal claim in January, 1822. On March 25, 1822, Lt. Mathew C. Perry commandeered the USS Shark, a schooner armed with 12 guns, sailed into Key West, and formally claimed the island as de facto property of the United States. Upon claiming the island, Perry renamed Key West to "Thompson's Island" and its harbor "Port Rodgers" in honor of the Secretary of the Navy, Smith Thompson, and War of 1812 hero and President of the Navy Supervisors Board, John Rodgers.
In 1823, Commodore David Porter of the USS Firefly, the flagship of a five-ship squadron tasked with the disruption of British trade in the West Indies, was granted control over Key West. With a large portion of wealthy merchant fleets operating through the island's ports, the waters of Key West became a significant point of interest for pirates to prey on shipping lanes. Key West's Naval base was established in 1823 (in what is now known as Mallory Square) to avert the theft of the island's merchant vessels. Porter, who ruled Key West under martial law as a military dictator, was delegated the assignment of counter-piracy and control over the island's slave trade. Key West was officially incorporated as United States property in 1828. Key West saw extensive growth beginning in the late 1820s, particularly in 1825 with the Federal Wrecking Act prescribing that all property wrecked in U.S. waters be taken to a U.S. Port of Entry. By request of the United States military, Key West later became a strategic position for anti-piracy in the West Indies. Among the first people to immigrate to Key West, the island saw an increase in Bahamian population during the mid 19th century. Their successive involvement in Key West's labor force were contributing factors in the island's growing maritime industries, particularly fishing, sponging, turtling, and shipbuilding.
After years of government lobbying for the establishment of military installations in Key West, the historic Fort Zachary Taylor was constructed in 1845 for the purpose of defending the southeast coast of the United States. Designed by U.S. Army Colonel, Joseph Gilmore Totten, and Simon Bernard, the fort was built with a large gunpowder magazine at either end of the barracks and was supported by two artillery batteries, Martello Towers, which still exist as the Martello Gallery-Key West Art and Historical Museum.
The 1840s saw three damaging hurricanes hit Key West. In October 1841, the Key West Hurricane of 1841 brought a storm surge to Key West that was the highest to date in the city's history, driving several ships ashore. Three years later, the Cuban Hurricane of 1844 passed east of Key West, but caused extensive damage to property and ships, with almost ten inches of rain recorded on October 5. Two years later the 1846 Havana hurricane struck Key West directly on October 11. The storm surge reached three feet higher than the floors of buildings on Duval Street. The Key West lighthouse and the Sand Key Lighthouse, on an island six miles from Key West, both collapsed, killing more than 20 people who had taken refuge in them. It was reported that only eight houses of some 600 in Key West were undamaged. Two cemeteries were washed out, with open coffins and bones scattered about.
Prior to the Civil War, increasing concerns of a conflict with the South prompted government officials to organize a seizure of Fort Taylor from Florida's possession. At midnight on Sunday, January 13, 1861, three days after Florida's secession, Captain James M. Brennan of the 1st U.S. Artillery Regiment transported 44 of his men from the Key West Barracks to Fort Taylor to secure their position from the Confederates. Brennan later sent a message to the central government in Washington requesting reinforcements and the presence of at least one or two warships in the harbor. Key West later became an important outpost for suppressing blockade runners, with the Union Navy using their strategic position as an operations headquarters for their East Gulf Blockading Squadron.
For the duration of the war, Key West stood as a stronghold for the Union's prevention of resource transport to the Confederacy through South Florida. 199 ships were captured by the blockade. Key West's salt production industry was temporarily shut down by the Union after in increase in Confederate sympathizers smuggling the product to the south. During the unsuccessful Ten Years' War for Cuban independence in the 1860s and 1870s, Key West became a major site for Cuban refugees. The island's subsequent rise in Cigar manufacturing and relocation of factories from Cuba were largely destroyed in Key West's devastating fire of April 1, 1886, resulting in the death of seven citizens and $1.5 Million in property damage across 50 acres of land. Following the sinking of the USS Maine in the Havana Harbor, roughly 24 bodies were buried the same year at the Key West's City Cemetery on 1 March 1898. A funeral was performed by Captain Bowman H. McCalla of the USS Marblehead and a statue memorial was erected in 1898 by the Encampment Union Veterans Legion, Washington D.C.

## 20th century

With the turn of the century came Key West's rapid growth following the extension of Henry M. Flagler's Florida East Coast Railway (FEC), connecting Key West with the Florida mainland via the newly constructed Overseas Railway. After initially becoming interested in connecting Key West to the mainland following the announcement in 1905 of the construction of the Panama Canal, Flagler partnered with project engineer James Meredith to establish a railway south through the Florida Keys. Throughout the course of seven years of construction, Flagler employed as a much as 4,000 workers and spent roughly $50 million in 17 million cubic yards of material for construction efforts. Several hurricanes in the early 20th century threatened to halt the project, including the devastating 1909 Florida Keys hurricane and 1910 Cuba hurricane the following year. The project was finally completed in 1912 and was considered the 8th wonder of the world by some, stretching 128 miles (206 km) from Homestead to Key West. On 22 January 1912, the Extension Special was the first train to arrive in Key West in the island's history. Regarded as the most intense hurricane to make landfall in the United States, the 1935 Labor Day hurricane caused significant damages to the Overseas Railroad, forcing Flagler to sell the railroad to Monroe County and the State of Florida $640,000. The following years saw Key West largest economic strife; 1934, the island was among the poorest city in the United States. In July the same year, the governor put the city under the control of the Federal Emergency Relief Administration. In 1938, the U.S. government rebuilt Flagler's railroad as an automobile highway as an extension of U.S. Route 1, becoming the Overseas Highway.
On December 18, 1917, the establishment of Key West's Naval Air Station was commissioned with U.S. Coast Guard Lieutenant Stanley Parker as commanding officer. The base soon became a major center for U.S. Naval aviation training and, quipped with a fleet of seaplanes and blimps, trained roughly 500 naval aviators during the First World War. Trumbo Point was originally built in 1912 to accommodate construction imports for the extension of the Florida East Coast Railway. However, with the acquisition by the U.S. Navy in 1917, the site was used as a seaplane base for the duration of the war. An early submarine base on Key West was established in the Fort Taylor Annex (what is now known as the Truman Annex). Thomas Edison resided in a home on the base in Key West for 6 months while perfecting 41 weapons for the US war effort and developing underwater ordinance for the Navy. The base was assigned the task of supplying U.S. fleets with oil and blocking German Naval vessels from reaching Mexican oil supplies.
Ernest Hemingway and his wife Pauline Pfeiffer moved to Key West in 1928 in home on 907 Whitehead Street, first built in 1848 by marine architect and salvage wrecker, Asa Tift. Pauline had first gained interest in the home while staying two-story home at 1301 Whitehead Street and eventually purchased the property for $8,000. Ernest used the property's carriage house as a writing studio, valuing the property's seclusion for his works. Pauline's addition of a swimming pool in 1937 was the first pool ever built in Key West. Ernest's 1935 non-fiction Green Hills of Africa, 1936 short stories "The Snows of Kilimanjaro", and "The Short Happy Life of Francis Macomber", were some of his most notable works written in Key West. Following their divorce in 1940, Pauline continued to live in the house until her death in 1951. The manuscripts of Ernest's 1970 posthumous novel, Islands in the Stream, were discovered in the property's garage. Upon returning to Key West, Ernest Hemingway began to work on the draft of his novel, A Farewell to Arms. In 1937, he published To Have and Have Not, written and set largely in Key West inside his home on Whitehead Street. Film adaptations, including To Have and Have Not (1944) and The Rose Tattoo (1955), set in Key West soon earned the island's reputation as an artistic haven.
With the onset of World War II, more than 14,000 ships were brought into the island's harbor; an almost doubling population occurred with arrival soldiers, sailors, laborers, and tourists. German U-boat operations occurred so close to Key West throughout the 1940s that locals often reported witnessing the burning wreckage of allied cargo and military freighters from the island's shore. "Meachum Field "(located in what is now known as Key West International Airport) was constructed as an additional satellite facility in 1940 to support blimps running anti-submarine patrols. In the same year, personnel from the Atlantic Fleet Sound School in New London, Connecticut, were transferred to the Naval Station, Key West, to create the Fleet Sonar School in the Truman Annex, tasked with training sonar operators to wage anti-submarine warfare against German hostiles. Following the end of the World War II, operations at Submarine Squadron 4 were transferred from Pearl Harbor to Key West in August 1945 as part of the U.S. Atlantic Fleet. The squadron was assigned commanding officers, Captains Edward S. Hutchinson and Lawrence Randall Daspit, respectively. The base was equipped with a fleet of one Fulton-class submarine tender, the USS Howard W. Gilmore (AS-16), one Chanticleer-class submarine rescue ship, the USS Petrel (ASR-14), a Balao-class submarine, the USS Clamagore (SS-343), which served as the squadrons flagship from January 1946 to August 1, 1959.
As relations between the U.S. and the Soviet Union deteriorated with the beginning of the Cold War, President Harry S. Truman made 11 trips to Key West to organize military defense plans while staying at the Little White House. In March 1948, Truman met with the Chiefs of the Armed Forces and the Department of Defense in Key West to discuss military fortification plans, known as the Key West Agreement. The agreement gave the Navy, Army, and Air force in increase of control over their aviation assets for reconnaissance, medical evacuation, and other tactical functions for the island's defense. With the establishment of Fidel Castro's regime after the Cuban Revolution in 1959, growing concerns over Soviet activity in Cuba led government officials to direct operations from South Florida military installations such as Homestead Air Force Base, Opa-Locka Marine Air Station, and the various U.S. Navy facilities in Key West.
An informal secession from the United States occurred in 1982 in Key West in response to a United States Border Patrol roadblock and inspection point on US 1. Numerous protests were sparked by the lack of accessibility into the Card Sound Bridge within the merger of Monroe County Road 905A/Miami-Dade County Road 905A where a Border Patrol checkpoint had been performing a narcotics and illegal immigrant search. After several failed complaints by the Key West City Council claiming that the roadblock would damage the island's tourism industry, Mayor Dennis Wardlow and the council declared Key West as an independent micronation on April 23, 1982.

## 21st century

In January 2005, former president Bill Clinton and his wife, then Senator Hillary Clinton, spent a weekend in the Harry S. Truman Little White House. Former President, Jimmy Carter, and his family stayed in the Little White House for the second time in 2007. It was the last time a United States President stayed in the home since John F. Kennedy had visited Key West in March 1961, and in November 1962. Prior to Kennedy, Dwight D. Eisenhower stayed at the Little White House following a heart attack in 1955. Named after Truman for his total of 175 days on 11 visits to the home, the Little White House was opened as a state historic site & museum in 1991. The homes office quarters were first used by president William Howard Taft in 1912. In 2001, an international summit was held by former Secretary of state, Colin Powell, in the Little White House. President Truman's most iconic items still remain on his desk in the museum today, including his briefcase, books, telephone, and the famous "The Buck Stops Here" sign.
Several landmarks in the Key West Historic District were added in the 21st century. Expanded in 1983 as a registered U.S. Historic district, the district includes the historic Sloppy Joe's Bar, added to the U.S. National Register of Historic Places in 2006. The Basilica of St. Mary Star of the Sea, added to the Register of Historic Place in 1971, was raised a minor basilica by Pope Benedict XVI on February 11, 2012. The Western Union, berthed at the Key West Bight Historic Seaport, underwent restoration work in 2008 as part of the Secretary of the Interior's Standard for Historic Vessel Preservation Projects. In 2016, the Southernmost House historic mansion was inducted into the Historic Hotels of America program.
On October 24, 2005, Hurricane Wilma made landfall on Key West as a Category 3 tropical cyclone. The 12th hurricane of the 2005 cyclone season, Hurricane Wilma brought the highest storm surge observed in the Florida Keys since the 1965 Hurricane Betsy. The island's first surge occurred at 2:30 am and reached heights of 5–6 ft (1.5–1.8 m) above mean sea level (MSL). The runway complex at Key West International Airport was temporarily inundated by six inches of seawater on the Atlantic coast of the island and sustained the highest recorded wind speeds of a 2-minute average of 71 mph (114 km/h). Major roadways, including Flagler Avenue and the intersection at U.S. Highway 1 and Cross Street, were damaged with up to four feet of flooding at midnight. On the Gulf Coast, Key West's Old Town neighborhoods experienced heavy inundation. Key West sustained roughly $100 million in damages with roughly sixty percent of the homes being flooded.
A vote was approved to add three amendments to the City Charter in 2020 that prohibited large cruise ships into the Port of Key West, sponsored Key West Committee for Safer, Cleaner Ships. The Port's cruise ship dock was originally opened in 1984 in Mallory Square and was met with disapproval by citizens that it would disrupt sunset watching on the square. In 2021, the Florida State Legislature overturned the amendments.In March 2024, Florida Governor Ron DeSantis approved renovation plans for Pier B, a project in which to service larger ships in the harbor.

## Industry

The fishing industry was the center of Key West's economy throughout the island's history. Throughout much of the 19th and 20th centuries, Key West supplied eighty percent of all turtle products in the United States. Turtle fishing off of Key West first appeared in records of Ponce de Leon's voyage 68 miles off of the island to the Dry Tortugas in 1513, in which his crew reportedly caught 160 Green sea turtles to satisfy their supply of food rations. The presence of sea turtles soon contributed to the island's name Las Tortugas, Spanish for "the turtles". The turtles, extracted for meat, eggs, and soup, became a lucrative resource for early fishermen in Key West. Sea turtles in the island's waters were captured using small enclosures used as traps made from wooden or concrete pillars situated near Key West's harbors where they could be quickly processed in nearby canning buildings. Soup canning, made often from the green pigment of the turtle shells, were an extensive part of Key West's exports from 1912 until 1952, when sea turtle population began to plummet throughout the Keys due to overfishing. In 1971, the Endangered Species Act was passed to allow the turtle population to recover, with the turtle and soup cannery buildings ceasing operations. On June 23, 1994, Key West's historic turtle Soup Cannery Buildings were added to the U.S. National Register of Historic Places.
Key West's wrecking industry contributed the island's wealthiest periods throughout much of the 19th century. Shipwrecks became a common occurrence in the Florida Keys with vessels from the Old World running aground in the region's shallow reefs. Indigenous Natives in Key West were often employed by local industries to salvage cargo from wrecked merchant vessels during the early 17th century, including a major salvaging by natives of the Spanish Fleet wrecked off of the Marquesas Keys in 1622. Salvaging of the remains of the Nuestra Señora de Atocha, wrecked off of Key West on 6 September, 1622, lasted for a duration of eight years by hired natives. On July 4, 1823, Key West's wrecking act, developed by the legislative council of the Territory of Florida, contained 14 sections ruling that salvagers were required to bring wrecked property into the United States territory and "report it to the nearest justice of the peace".
As a result of the newly formed wrecking industry, the Pensacola Gazette reported in 1826 that gross duties paid on goods landed in Key West increased from $389 in 1823 to $14,108 in 1824. On March 3, 1825, U.S. Congress passed the Federal Wrecking Act, mandating all property wrecked off of U.S. waters be brought in to the nearest U.S. port of entry. The following year, John Simonton reported that "from December, 1824, to December, 1825, $293,353.00 of wrecked property" was sold in Key West with the establishment of Superior Court in Key West of maritime and admiralty jurisdiction mandating that all Florida Keys wrecking property be taken to Key West.
In 1867, New York City-based cigar manufacturer, Samuel Sidenberg, established the first "clear Cuban" cigar factory in Key West. The island's devastating fire in 1886, destroying 18 cigar factories in Key West, left thousand employees without work and resulted in many factory owners to relocate their operations to Ybor City in Tampa. The subsequent loss of cigar factories in Key West lead to the eventual decline of the island's lucrative industry in the late 19th century. Key West significant sponging industry was also disrupted during the event. The Key West sponge industry originated with the discovery of large sponge beds in the shallow waters of Key West's reefs in the 19th century, enabling the production of roughly 2,000 tons of sponge products per year. At one point, Key West held a monopoly on the United States sponge trade and contributed to the first sponge shipment to New York City in 1849. Employing 1,200 men, sponging raised Key West's economy $750,000 annually by the mid-18th century.