History of Florida
Map ofFlorida et Regiones Vicinae from ca. 1640
Topics Cities Bartow Fort Lauderdale Gainesville Key West Sarasota St. Augustine West Palm Beach Ybor City Counties Brevard County Palm Beach County Politics Women's suffrage in Florida
Timeline Pre-history, until 1497 Spanish Rule, 1513–1763 British Rule, 1763–1783: American Revolutionary War, 1775–1783 Spanish Rule, 1783–1821: War of 1812, 1811–1814 First Seminole War, 1817–1818 U.S. Territorial Period, 1822–1845: Capitol moved toTallahassee, 1824 Second Seminole War, 1835–1842 Constitutional convention, 1838 Statehood, 1845–present: Third Seminole War, 1855–1858 Ordinance of Secession, 1861 Civil War, 1861–1865 3rd Constitution, 1865 Reconstruction, 1865–1868 4th Constitution, 1868 5th Constitution, 1885 Great Migration, 1910–1930 Land Boom, 1925–1929 6th Constitution, 1968 Gore v. Harris,Presidential Election, 2000 COVID-19 pandemic, 2020–2022
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Thehistory ofKey West begins thousands of years prior to recordedEuropean contact, when the island became largely occupied by theCalusa andTequestaNative American tribes. By the end of theAge of Discovery, Key West's indigenous history had largely diminished; brief settlements by transientSeminoles in the late 18th century introduced temporary trade in the surroundingFlorida Keys, with early fishing andwrecking revenues becoming lucrative among passingNatives in the region. The island's first documented exploration byEuropeans occurred in 1513 by theSpanish explorerJuan Ponce de León while attempting to reach Florida'sGulf Coast.^{[note 1][1]} 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.^{[note 2][2]} Although ownership was claimed by the Spanish explorers, no permanentsettlement had been established, and possession of the island was briefly asserted by theBritish Empire in 1763.^[3]

FollowingSpain's cession ofFlorida to theUnited States in 1819, the first permanentcolonization of Key West began with American possession in 1821.^[4] Legal claim of the island occurred with the purchase by businessman John W. Simonton in 1822, in whichfederal property was asserted only three months later with the arrival ofU.S. Navy LieutenantMatthew 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.^[5]

Shortly afterFlorida's secession from the United States in 1861,Federal forces seizedFort Zachary Taylor, securing their position in Key West as a stronghold for the duration of the ensuingAmerican Civil War.^[6] TheEast Gulf Blockade Squadron, established on the island by theUnion Navy to restrict supplies reachingConfederate ports, played a significant role in supportingUnion blockade operations in theGulf of Mexico during the conflict with the South.^[7] With the completion ofHenry Flagler'sOverseas Railroad in the early 1910s, Key West was connected to the Florida mainland with Flagler's extension of theFlorida East Coast Railway (FEC).^[8] In the years prior to theCuban Revolution in 1953, frequent transport closely linked Key West and Havana. During theCuban Missile Crisis, the island later became a strategic position for installation ofmissile defense systems and military personnel in the event of a sudden attack fromCuba. In his speeches regardingFidel Castro, PresidentJohn 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 the20th century as that of a significant "artistic haven".^[9] The island washome to novelistErnest Hemingway for eight years, during which he wrote several of his major works. It also served as a longtime residence for playwrightTennessee Williams, who spent much of his later life on the island. In subsequent decades, Key West hosted a number of prominent writers, includingJohn Hersey,Wallace Stevens,Robert Frost,Elizabeth Bishop,Shel Silverstein, andThomas McGuane, as well as various musicians and celebrities such asJimmy Buffett,Jerry Jeff Walker,Richard Burton, andSally Rand.^[9]

According toUSGS geologists, Barbara Lidz and Eugene Shinn, thegeological history of Key West coincides with the earlysedimentary development of the Florida Keys in the latter part of thePleistocene andHolocene epochs in the last 500 million years.^[10] Earlydeposition resulted in the accumulation of Pleistocenelimestone over 200 feet in width in the Lower Keys. Key West and the Lower Keys are categorized geologically by their particularcoralloid composition, sometimes classified as the High Coral Keys, Low Coral Keys and the Oolite Keys for their early foundation of sandbars andooid composition.^[11] 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 shallowsandbars andoolite 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 ofcalcium carbonate laying above Miami Colite limestone.^[12] The reduction of sea levels from the formation ofglaciers during theIce 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 shallowsand cays as it would be known as by human settlers. These shoals were shallow enough to facilitatephotosynthesis and the development ofcoral reefs.^[13] As sea levels continuously lowered during the following periods of geological formation, the Florida Keys was eventually disconnected from theFlorida 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 theAtlantic.^[14]

Historian John Viele traces possible human occupation of Key West to 3000B.C.E,^[15] with indigenous groups related toCalusas,Matecumbes,Tequestas, and lateSeminoles possibly settling in more than 800islands in the Florida Keys. According to contemporary historian Jerry Wilkinson, the dominant inhabitants of the Florida Keys were likely the Calusa, however, the discovery ofpottery fragments later indicated the presence of Tequesta and possibly evidence forCaribbean Island Natives.^[16] Wilkinson posits further archeological evidence indicating that the Calusa occupants may have functioned as aconfederation composed of smaller tribes such as the Tequesta,Ais, orJeaga.^[17] Primarilyhunter-gatherers, the island's abundant source of fish, turtle,lobster,shellfish, andmanatees provided native settlers with copiousstaple foods and even the installation of temporary trade outposts by later Seminoles.^[18] Spanish documents record a "Chief of the Key Bones", referring to a possible tribal leader or earlychiefdom on Key West.^[18] During the period of Spanish control, many of Key West's native groups adopted aspects of the Spanish language,customs, andsurnames, with evidence of the use of Spanish titles such as "captain-gener-al" "bishop", and "king" by Native leaders.^[19]

Upon sighting Key West during hisvoyage south along the keys in 1513, Ponce de León and his Spanish fleet adopted the island's original name ofCayo Hueso (Spanish pronunciation:[ˈkaʝoˈweso]). The initial discovery of driedhuman 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 ascommunal graveyard.^[20] In his correspondence with the lawyer and politicianJohn 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."^[21] On the presence of Natives, Whitehead notes evidence offortifications, possible burial grounds, and human bones initially believed to be rocks.^[22] 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:

In his early years he had heard it stated that some eighty or ninety years previous, (probably about the commencement of the eighteenth century) the Indians inhabiting the Islands along the coast, and those on the main land, were of different tribes, and as the Islanders frequently visited the main for the purpose of hunting, a feud arose between the two tribes, and those from the main having made an irruption into the Islands, their inhabitants were driven from island to island until they reached Key West. Here, as they could flee no farther, they were compelled to risk a final battle, which resulted in the almost entire extermination of the islanders. Only a few escaped, (and that by a miracle, as they embarked in canoes upon the ocean) whose descendants, it is said, were known to have been met with in the Island of Cuba.

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 theKingdom of Great Britain in1763, 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, possibleanglicization during British authority likely altered the name ofCayo Hueso ("Bone Cay") to a modifiedKey West in following years.^{[note 3][20]} 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."^[23] 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 wineXeres Seco into 'Sherry Sack,' corrupted into Key West."^[23]

With the onset ofBritish control of Florida, Key West become mostly uninhabited, with neither the arriving British nor Spanish exercisingde facto control.^[24] In 1766,Major general andEast 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.^[25] Grant consisted of no means to prevent the situation.^{[note 4][26]}

For much of the 18th century,smugglers andprivateers used the island to conceal valuables, while Bahamians and Cubans often visited for fishing and other various forms of resource manufacture.^[27]British expansion westward in theThirteen Colonies prompted the immigration south by many of theCreek Indian Nation in the early 1700s. These migrants, who settled much in Florida, came as far as Key West in 1770.^[28]Raids by outside natives in the early 1700s, supported and sometimes led by the British,^[24] resulted in the destruction of severalSpanish missions in Florida.^[29] 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.^[24]

During the early 19th century, with neither Spain nor Britain maintaining effective authority over Key West, residents of Havana continued to issuefishing licenses tovessels in the British territory.^[25] On 26 August 1815, theRoyal Spanish Navy Artillery officer, Juan Pablo Salas, acquired a Spanish land grant of Key West fromJuan José de Estrada,^[30] the7th governor of Spanish East Florida, for his "meritorious service to theKing of Spain".^[31][20] Six years later on 21 December, 1821, the American businessman fromMobile, Alabama, John W. Simonton offered to purchase Sala's land grant for $2,000.^[32] Simonton, whoJefferson B. Browne writes was initially attracted by Key West's "advantageous situation and capacity of the harbor"^[33] and its proximity to majorshipping lanes,^[34] conducted the purchase with Salas while meeting in Havana following Spain's formal cession of Florida to the United States in 1821.^[20]

Eager to sell the island, Salas had initially sold Key West for a total of $575 to a former governor ofSouth Carolina, GeneralJohn Geddes, who was unable to secure the rights before Simonton, assisted by influential friends fromWashington D.C., asserted legal claim in January, 1822.^[35] During the purchasing process, Simonton was joined by three business partners—John Whitehead, John Fleeming (now spelled Fleming), and Colonel Pardon C. Greene. Soon after the purchase, Simonton sold half of his interest to John Whitehead and John W. Fleeming, both then of Mobile, Alabama. He sold an additional quarter interest to John Warner and John Mountain, whose share was later vested in Greene, who resided on the island. The island was subsequently divided into three separate properties, each allocated to one of these partners.^[22][36] As a result, Simonton, Whitehead, Fleeming, and Greene were hailed the "founding fathers" of Key West by theKeys Weekly Newspapers.^[37]

During his business travels between ports in the Gulf of Mexico and the eastern seaboard, John Whitehead often saw Key West but never stopped there. His first visit to the island was unplanned. While sailing from Mobile, Alabama, toNew York City, the ship he was on was wrecked in the Straits of Florida. When wrecking crews arrived to salvage cargo from the shipwreck, they transported the passengers, crew, and John Whitehead to Key West. Following his arrival, Whitehead explored the island.^[37] Key West’s Whitehead Street, which runs roughly north-south through Old Town, is named after John Whitehead.^[38]William A. Whitehead, a native ofNew Jersey, joined his elder brother John in Key West in 1828 and quickly became a prominent figure in the developing community. In 1829, he conducted a survey of the town after Key West received its first government charter. In 1830, Whitehead was appointed collector of customs; during the same year, he was in charge of Key West’s port of entry.^[39][38]

On March 25, 1822, Lt. Matthew C. Perry commandeered theUSSShark, aschooner armed with 12 guns, sailed into Key West, and formally claimed the island asde 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 theSecretary of the Navy,Smith Thompson, andWar of 1812 hero and President of the Navy Supervisors Board,John Rodgers.^[40] Following the signing of theAdams–Onís Treaty in 1819 by Secretary of State,John Quincy Adams, and Foreign Minister of Spain,Luis de Onis, thousands of tracts ofcoral and Atlantic shallows offshore of the Florida Keys (what now makes up theFlorida Reef), was made an extension of U.S. soil. "An Act to Protect the Commerce of the United States, and Crimes of Piracy"^[41] was signed into law and authorized by PresidentJames Monroe to create a special unit of the Navy, that would be known as theWest Indies Squadron, to combat piracy and the slave trade in the waters surrounding Key West and the Florida Keys. CommodoreJames Biddle was named the squadron's first commander and was assigned a fleet of 14 ships. Biddle employed mostly heavy-drafted ships that proved to be ineffective in the pursuit of pirates who favored shallow-drafted vessels for agile navigation in theshoals andreefs of theWest Indies.^[41]

In 1823, Secretary Smith Thompson replaced Biddle with CommodoreDavid Porter of theUSSFirefly, theflagship of a five-ship squadron tasked with the disruption of British trade in the West Indies, and granted him control over Key West.^[43] With a large portion of wealthymerchant 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; in order to combat the piracy, Porter organized the “Mosquito Fleet”: his command of 10Chesapeake Bay schooners, five swift shallow-drafted vessels, and the steam-powered USSSeagull.^[44][45][46] Key West's Naval base was established in 1823 (in what is now known asMallory Square) to avert the theft of the island's merchant vessels. Porter, who ruled Key West undermartial law as a military dictator, was delegated the assignment of counter-piracy and control over the island'sslave trade.^[47] In 1831, Porter noted the strategic value of Key West's military outpost:

The advantages of Key West's location as a military and naval station has no equal except Gibraltar. ... It commands the outlets of all trade fromJamaica, theCaribbean Sea, theBay of Honduras, and the Gulf of Mexico, and is a check to the naval forces of whatever nation may hold Cuba.

Porter wascourt-martialed after invading the town ofFajardo, Puerto Rico and resigned from the U.S. Navy on 18 August, 1826.^[49] Two years later, Key West was officially incorporated as United States property in 1828.^{[note 5]} The first actincorporating the "City of Key West" was passed on 8 January, 1828. However, on 8 November, 1828, this act was repealed and replaced by a new one incorporating the "Town of Key West".^[50] The island saw extensive growth beginning in the late 1820s, particularly in 1825 with the Federal Wrecking Act prescribing that all property wrecked inU.S. waters be taken to aU.S. Port of Entry. Between 1823 to 1830, Key West's population rose from nearly 400 to 500 inhabitants. 20 years later, Key West would be home to roughly 2,500 residents.^[46]

In 1827, the United States Senate passed a bill to establish a territorial court with admiralty jurisdiction at Key West. This legislation initially faced opposition from residents in northern Florida, who had good chances of blocking it. However, John W. Simonton traveled to Washington, D.C., and presented a formal petition to Congress advocating for the bill’s approval. As a result, in 1828 Congress enacted the bill creating a territorial (or federal) court at Key West, known as the "Superior Court," with jurisdiction over the southern part of the territory. JudgeJames Webb of Georgia was appointed as the first judge of the Superior Court in 1828. He served until his retirement in April 1838, after which he moved to Texas and became a secretary there. He was succeeded in 1839 by Mitam Fain, M.D., who held the position until Florida’s admission to the Union in 1845. In 1847, theUnited States District Court for the Southern District of Florida was established.^[51]

Authority was granted to a board consisting of seven town council members, who were elected by free "white male persons" aged twenty-one or older, provided they had lived within the designated boundaries for a minimum of three months.^[50] The council’s president simultaneously acted as mayor, carrying out mayoral responsibilities and also fulfilling the role of justice of the peace for the territory, including collecting associated fees. Besides typical municipal functions, the council uniquely held the power to appointmaritime pilots, oversee pilotage regulations, and enforce laws both from the territory and those locally enacted. In 1832, the incorporated town was replaced by an incorporated city following the issuance of a charter by the territorial council. This charter established the framework for electing a mayor along with six council members. To be eligible to vote, residents had to have lived in the city for at least twelve months. ColonelOliver O'Hara became the first mayor elected under this new charter.^[50]

In 1832, there were eighty-one buildings within the city limits, including storage sheds for wrecked cotton and other goods, as well asblacksmith shops. The two most prominent structures were the warehouses owned by Pardon C. Greene andFielding A. Browne, each valued at $6,000, including the land and wharfs. In 1835, the territorial council abolished the city charter under circumstances that were unclear to most residents. However, the repeal stipulated that all existing ordinances would remain effective. Upon learning of this, local citizens petitioned Congress to oppose the decision. The Congressional Committee on Territories reviewed the situation and recommended reinstating the charter, leading the territorial council to restore it in 1836.^[54]

By request of theUnited States military, Key West later became a strategic position foranti-piracy in the West Indies. Among the first people to immigrate to Key West, the island saw an increase inBahamian population during the mid 19th century.^[55] Their successive involvement in Key West'slabor force were contributing factors in the island's growing maritime industries, particularly fishing,sponging,turtling, andshipbuilding. In addition to a number of Bahamian migrants, Key West's population boom throughout the 1830s consisted of newcomers of English descent from the Bahamas, many of whom were relatives ofLoyalists who had fled theAmerican Revolution. This influx was complemented by settlers from southern, eastern, andNew England states, who established homesteads and contributed to the town’s growing diversity. The demographic expansion also included both enslaved andfree Blacks, arriving from various parts of the United States and the West Indies.^[56]

Constructed in the 1820s on the corner of Caroline and Whitehead Streets, a one-storycedarwood house is recorded as the oldest house in Key West, and among theoldest in South Florida.^[57][58] Around 1832, the home was moved by a mule team to its present location on 322 Duval Street and purchased by Captain Frances Watlington in 1839. The house currently serves as the Wrecker's Museum after being donated to the State of Florida in 1974.^[57] As maritime activity around the island increased, the originalKey West Lighthouse was built on the southern tip of the island in 1825. After it was destroyed during a hurricane in 1846, a replacement was built further from shoreline to 938 Whitehead Street. Built 56 feet high, it became the third-oldest brick lighthouse in Florida.^[59] As multi-storied buildings developed during Key West's economic growth and obscured theLighthouse's beacon, 20 feet were added to its height. The property was purchased by American politician and then Key West customs collectorStephen Mallory from John Whitehead for $200.^[60]

After years of governmentlobbying for the establishment ofmilitary installations in Key West, the historicFort Zachary Taylor was constructed in 1845 for the purpose of defending thesoutheast coast of the United States.^[61] Designed byU.S. ArmyColonel, Joseph Gilmore Totten, and Simon Bernard, the fort was built with a largegunpowder magazine at either end of the barracks and was supported by twoartillery batteries,Martello Towers, which still exist as theMartello Gallery-Key West Art and Historical Museum and theWest Martello Tower (which now serve as the Key West Garden Club).^[62] Originally built in 1861, the first official railroad in Key West was a small track that connected the two Martello Towers with Fort Taylor.^[63] Fort Taylor was built on an almost 13-acre island roughly 440 yards off of the southwest shore of Key West. Set in 10 feet of water, the fort was connected to Key West by a 720-foot long woodendrawbridge.^[64] Construction of Fort Taylor was frequently hampered by bouts ofyellow fever, and less than a year after work began, the hurricane of 11 October, 1846, caused significant damage to the site and resulted in the deaths of four workers.^[64] Named for PresidentZachary Taylor, the fort was built of brick and local coral rock harvested offshore. Construction was completed in 1866, a year after the Civil War ended.

During the Civil War, Fort Zachary Taylor gained the reputation of serving as the "Gibraltar of theStraits of Florida"^[65] or the "Gibraltar ofthe Gulf",^[66] referring to its significance in defending U.S. interests against European powers and headquartering the East Gulf Blockading Squadron. Major James Glassel of the U.S. Army dispatched two companies of infantry to Key West in February 1831, establishing soldier's barracks on the northern side of the island. The encampment was complete with officer's quarters, a guard house, and several additional buildings.^[67]

The 1840s saw three damaging hurricanes hit Key West. In October 1841, theKey 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.^[68] Three years later, theCuban Hurricane of 1844 passed east of Key West, but caused extensive damage to property and ships, with almost ten inches of rain recorded on 5 October.^[69] Two years later the1846 Havana hurricane struck Key West directly on 11 October. The storm surge reached three feet higher than the floors of buildings on Duval Street. The Key West lighthouse and theSand 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.^[70]

Prior to the Civil War, increasing concerns of a conflict withthe South prompted government officials to organize a seizure of Fort Taylor from Florida's possession.^[71] On 11 December, 1860, Lieutenant ColonelLorenzo Thomas of theU.S. Army, disturbed by the Union's vulnerable position in Key West, reported inthe Official Record of the Union and Confederate Armies that:

The present condition of affairs in this State indicates very clearly that Florida, by the act of her people, will succeed from the Federal Government. I have reliable information that as soon as the act is committed an attempt will be made to seize upon Fort Taylor. I therefore request instructions on what I am to do- endeavor at all hazards to prevent Fort Taylor being taken or allow State authorities to have possession.

At midnight on Sunday, 13 January, 1861, three days after Florida's secession, Captain James M. Brennan of the1st U.S. Artillery Regiment transported 44 of his men from the Key West Barracks to Fort Taylor to secure their position from theConfederates.^[72] Brennan later sent a message to the central government in Washington requesting reinforcements and the presence of at least one or twowarships in the harbor.

Construction of the U.S. military coastal fortress,Fort Jefferson onGarden Key (70 miles west of Key West), began in 1845 after a survey conducted by Commodore John Rodgers in 1829 stated that a military outpost in theDry Tortugas would provide a strong naval advantage within theGulf Coast. With the beginning of the Civil War, 62 men of MajorLewis Golding Arnold's Second U.S. Artillery Regiment were transferred to the fort to prevent it from falling into rebel hands. A drill on 26 January, 1861, was performed by the fort's Superintending Engineer, CaptainMontgomery C. Meigs, to test the integrity of the post'sartillery. The weapon's capabilities proved disappointing, as it took twelve primers to fire two rounds. The vessel,Brooklyn, anchored briefly on Garden Key on 2 February to unload twelvemountain howitzers before traveling toPensacola. 160 soldiers of Col.Bill Wilson's6th New York Infantry Regiment was transferred to Fort Jefferson on 4 July, 1861. New York soldiers were relieved in March 1862 when the7th New Hampshire Volunteer Infantry arrived under the command of Col.Haldimand S. Putnam. New Hampshire soldiers were relieved in June 1862 with the arrival of the90th New York Volunteer Infantry Regiment under the command of Lt. Col. Louis W. Tinelli. New York soldiers were replaced with the47th Pennsylvania Infantry Regiment in December 1862. Two years later, the110th New York Volunteer Infantry arrived in March 1864.^{[73]: 49, 55–57, 63–65, 78–79} After being convicted of conspiracy for housing assassinJohn Wilkes Booth, Dr.Samual A. Mudd was among the fort's most infamous prisoners.^[74][75]

Key West later became an important outpost for suppressingblockade runners, with theUnion Navy using their strategic position as an operations headquarters for theirEast Gulf Blockading Squadron.^[76] Through the course of the war, the Union Blockade captured and imprisoned about 299 captured blockade runners, as well civilians whom were disloyal to the Union, in Fort Zachary Taylor.^[65] For the duration of the war, Key West stood as a stronghold for the Union's prevention of resource transport to the Confederacy throughSouth Florida. 199 ships were captured by the blockade.^[77] 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.^[78]

During the unsuccessfulTen Years' War for Cuban independence in the 1860s and 1870s, Key West became a major site forCubanrefugees.^[79] On 11 November, 1871, a Cubanheritage center and museum, theSan Carlos Institute, was founded by members of Key West's exile community on Anne Street in Old Town. The institute served as a center for organizing efforts in support of Cuban independence from Spain. Key West community leaders José Dolores Poyo and Juan María Reyes proposed the creation of the organization to promote Cuban cultural identity and nationalist ideals.^[80] In his first visit to Key West, Cuban revolutionaryJosé Martí addressed a large gathering at the institute on 3 January, 1892, and announced the formation of a united front to lead the effort for Cuban independence.^[81]

At the time, while the Spanish Empire was engaged in a conflict with Cuban revolutionaries, financial and material assistance routed through Key West was crucial. The island’s cigar industry was integral to this support network, processing Cuban tobacco and facilitating the flow of funds to insurgent forces. According to certain interpretations, by targeting Key West’s cigar factories, Spanish authorities sought to disrupt a principal source of funding for the revolutionaries, thereby impairing their operational capabilities. Key West represented a primary conduit for revolutionary support, with limited alternative channels available.^[82] In 1874, the San Carlos Institute moved to a much larger facility on Fleming Street before it was ultimately destroyed in the City's fire of 1886. After its replacement was demolished by a hurricane in 1914, the institute was rebuilt at its present location on Duval Street.

The island's subsequent rise in Cigar manufacturing and relocation of factories fromCuba were largely destroyed in Key West's devastatingfire of 1 April, 1886.^[83] The fire was one of the most catastrophic events in the island’s history, resulting in the death of seven citizens and $1.5 Million in property damage across 50 acres of land.^[79] The origin of the fire was discovered to be at the San Carlos Institute by a watchman at approximately 1:45 a.m. on 30 March.^[84] Propelled by the wind, the blaze quickly spread to adjoining buildings and throughout the town, destroying the Episcopal and Baptist churches, the Masonic Hall, several cigar factories, and the bonded warehouse containing nearly a quarter-million dollars’ worth oftobacco. With the city’s cisterns largely dry and no functioning water supply, officers from the U.S. Navy steamersBrooklyn andPowhatan resorted to demolishing buildings with explosives in an attempt to stop the fire. The flames soon reached the business district, consuming structures filled with valuable merchandise.^[83] The 12-hour-long fire was battled by three of the City's volunteer fire companies under the command of Fire Chief Benjamin Franklin H. Bowers, along with aid from local military personnel.^[85] The heat from the blaze was so intense that firefighters were frequently forced to retreat. Combined with a lack of equipment and water, these conditions led to the destruction of much of the town’s core. A total of six wharves and five brick warehouses were destroyed.^[83]

On 24 January, 1889, theUSSMaine left Key West for Havana to protect American interests in Cuba and conduct winter naval exercises in the Gulf of Mexico during theCuban War of Independence.^[86] Prior to its voyage to Havana, theMaine loaded coal to Fort Jefferson. Three weeks later on the night of 15 February, 1889, while anchored at theHavana Harbor, an explosion occurred on theMaine'sbow after more than 5 tons ofgunpowder charges for the vessel's forward batteries had detonated. 251 enlisted sailors of the ship's crew of 355 men were killed. The incident led to an increase in tensions between the United States and Spain. A U.S. Naval inquiry led by CaptainWilliam T. Sampson was conducted in the Key West Customs House to investigate the cause of the blast. Upon ruling that the explosion had occurred from an externaltorpedo detonation, the United States declared war on Spain on 25 April, 1898, marking the onset of theSpanish-American War. Shortly after the incident in Havana, the U.S. Navy began increased efforts to prepare Key West for military base use. Large stocks of ammunition and coal were sent to Key West to strengthen fortifications; Fort Zachary Taylor was supplied with two12-inch M1895 guns for south Battery Osceola and Four3-inch M1898 15-pounder rapid-firerifles to Battery Adair.^[87]

Beginning in 1885, trolleys operated by theKey West Street Car Company served as a primary mode of transportation throughout Key West. Later, tours of the island were performed aboardelectric railway cars run by the Key West Electric Company.^[88] Although the Key West Extension of the Florida East Coast Railway ceased operations following partial destruction by a hurricane in 1935, the Conch Tour Train now functions as the closest experience to a railway in Key West.^[89]

Before ice was manufactured locally in 1890, ships imported natural ice to Key West from New England, with local salvager and entrepreneurAsa Tift constructing anicehouse beside theship chandlery and cisterns originally built by A.C. Tift & Company. The ship chandlery was originally constructed in 1879 by salvager William H. Wall to serve as the warehouse for Wall & Company. The building was one of the earliest brick structures to be erected in Key West, and in 1884, Wall sold the nearly 154-foot-long building to Tift, who turned it into the waterfront chandlery.^[90] The former chandlery now serves as the chamber of commerce, while the former icehouse serves the Shell Warehouse.^[91]

Construction of Key West'sU.S. Customs House began in 1889 besides the wharf in order to house federal offices of the courts, customs, postal, and lighthouse services.^[92][93] Designed by theIrish-born architectWilliam Kerr fromBallyboley, County Down, local materials and labor on the island were scarce, so nearly 1 million bricks were needed to be transported from New York and iron was imported fromPennsylvania.^[94] The total cost of construction was $108,000, approximately $3.49 million as of 2025^[update].^[93]

On 7 May, 1898, theU.S. Navy's Atlantic Fleet was moved to Key West by CommodoreGeorge C. Remey of theUSSLancaster for the remainder of the war. With the arrival of the Navy on Key West during the height of the conflict, numerous affairs were made to prepare the island for base use.Coal bunkers large enough to hold 15,000 tons of coal were dug throughout Key West. Coal was temporarily stored insail barges in the harbor while coal bunkers were undergoing construction. Additionally, intensivedredging of the island's harbor had been conducted by the Army in order to extend military fortification off Key West's shore; private owners ofdocks,warehouses, andwharves, leased their properties to the military to help with war efforts, and highexplosives and ammunition were stored in a number of newly built ordnance depots.^[95][96]

Following the sinking of theUSS Maine in the Havana Harbor, roughly 24 bodies were buried the same year at theKey West's City Cemetery on 1 March 1898. A funeral was performed by CaptainBowman H. McCalla of theUSS Marblehead and a statue memorial was erected in 1898 by the Encampment Union Veterans Legion, Washington D.C.^[97][98]

With the turn of the century came Key West's rapid growth following the extension ofHenry M. Flagler'sFlorida East Coast Railway (FEC), connecting Key West with the Florida mainland via the newly constructedOverseas Railroad.^[99] After initially becoming interested in connecting Key West to the mainland following the announcement in 1905 of the construction of thePanama 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.^[100] Several hurricanes in the early 20th century threatened to halt the project, including the devastating1909 Florida Keys hurricane and1910 Cuba hurricane the following year. The project was finally completed in 1912 and was hailed the8th wonder of the world by some residents,^[79] stretching 128 miles (206 km) fromHomestead to Key West.^[79]

Both the 1909 and 1910 hurricanes caused significant damage to Key West. On 11 October, 1909, winds reached up to 94 miles per hour, with 8 to 10 inches of rainfall. More than 400 buildings were displaced by the storm surge or collapse due to the high winds; the weather bureau building onSand Key was also swept out to sea, along with sections of the Overseas Railroad that were still under construction.^[101] Fifteen people were confirmed dead as a result of the storm, and over 300 boats were destroyed in the island's Harbor, resulting in a total of $1 million in damages accumulated from the hurricane.^[102]

On 22 January 1912, theExtension Special was the first train to arrive in Key West in the island's history. Arriving in his private railcar, Henry Flagler was welcomed by local residents bands and a celebratory parade.^[103] The following year, Flagler died at the age of 83 fromTuberculosis. Regarded as one of the most intense hurricanes to strike the United States, the1935 Labor Day hurricane caused extensive damage to the Overseas Railroad. As a result, the line was sold by the Florida East Coast Railway toMonroe County and the State of Florida for $640,000.^[104] Wind gusts were measured reaching as high as 150 to 200 miles per hour.^[105] InIslamorada, approximately 35 miles of railroad track were destroyed by storm tides reaching 18 to 20 feet. A rescue train was swept off the tracks, and nearly 300World War I veterans, employed through a federal relief program, were killed in the storm.^[105] Three years later, the U.S. government rebuilt Flagler's railroad as an automobile highway as an extension ofU.S. Route 1, becoming theOverseas Highway in 1938.

On 18 December, 1917, the establishment ofKey West's Naval Air Station was commissioned withU.S. Coast Guard Lieutenant Stanley Parker ascommanding officer.^[106] The base soon became a major center for U.S.Naval aviation training and, quipped with a fleet ofseaplanes and blimps, trained roughly 500 naval aviators during theFirst World War.Trumbo Point was originally built in 1912 to accommodate construction imports for the extension of the Florida East Coast Railway.^[107] 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 earlysubmarine base on Key West was established in the Fort Taylor Annex (what is now known as theTruman Annex).Thomas Edison resided in a home on the base in Key West for 6 months while developing 41 weapons for the US war effort and developing underwater ordinance for the Navy.^[108] The base was assigned the task of supplying U.S. fleets with oil and blockingGerman Naval vessels from reaching Mexican oil supplies.

Key West's Naval stations saw extensive expansion with the onset of theFirst World War. A year after the outbreak of World War I in 1915, the Naval Station onBoca Chica Key included 101 acres, 55 buildings, coal sheds with a 50,000-ton capacity, a machine shop, a marine railway with a 750-ton capacity, a small hospital, and 100 to 300 personnel of civilian workforce.^[109] A landfill was used for the construction of Key West'sFlemming Key to hold a number of the island's military installations. On 13 July, 1917, three months after the United States' entry into World War I, land rented from the F.E.C Railway, what is now known asTrumbo Point, was used for the construction of a new coastal air patrol station. The land consisted of a dredging contract with 134 acres of landfill pumped up from the water's bottom. On 22 September, aCurtis N-9seaplane was piloted by U.S. Coast Guard Lieutenant Stanley Parker and was logged as the first naval flight from Key West. Numerous U.S. Navaldestroyers,submarines,submarine chasers, andpatrol vessels conducted training and patrol operations off the coast of Key West from the Naval Station and from a Section Base in downtown near Duval street.

With World War I drawing to close in 1918, Key West's submarine and air station were decommissioned with multiple buildings at the Trumbo Annex being dismantled. Military activity in Key West greatly decreased following the end of the war, with the island's facilities mainly being used for minor seaplane training. A radio wireless station was established in the Truman Annex and was used by the Navy throughout the 1920-30s.^[110] A project initiated in 1917 to construct a submarine basin on the island's harbor was finished in 1920 and saw frequent use with the beginning of the 1940s. Military activity in Key West slowly re-emerged with an increase in sightings ofGerman U-boat presence off the Gulf of Mexico and the Florida Keys.^[111] In 1939, theUnited States Lighthouse Service merged with the Coast Guard, establishing the island'sCaptain of the Port Key West.^[112]

In 1926,Carl Tänzler emigrated fromGermany to the United States, eventually settling in Florida. Adopting the name Carl von Cosel, he became employed as aradiology technician at the U.S. Marine Hospital in Key West.^[113] On 22 April, 1930, von Cosel examined a youngCuban-American patient,Maria Elena Milagro de Hoyos, who had been diagnosed with tuberculosis. Captivated by her appearance and believing she was the woman foretold to him in visions during his youth, von Cosel developed an obsessive infatuation. Despite her worsening condition and repeated treatments administered by von Cosel, Hoyos died in October 1931. After removing her body from the Key West Cemetery in 1933, von Cosel brought it to his makeshift laboratory and later moved it into the airplane-shaped structure in his backyard, where he lived with the preserved corpse until 1940, when his actions were discovered by Elena's family and authorities. This case has since become widely recounted in local histories.^[114][115]

On 19 July, 1927, the newly founded airlinePan American Airways (Pan Am) received a mail contract authorizing flights between Key West and Havana.^[116] The first of these flights occurred on 19 October when theFairchild FC-2 float planeLa Nina was chartered by Pan Am to fly from Key West to Havana. As construction commenced on a company-commissioned runway at Meacham Field, Pan Am expanded its Key West fleet with the addition of threeFokker F-VIItrimotor aircraft.^[116] Scheduled mail flights officially began on 28 October, 1927.^[116] On 16 January, 1928, Pan American Airways expanded its operations to include regular passenger service between Key West and Havana, with a one-way fare of $50 for a 75-minute flight.^[117]

During theGreat Depression, Key West's municipal government had issuedrevenue bonds, backed by anticipated tax revenues or service fees, to finance essential public services and infrastructure. By around 1933, the city had defaulted on several millions of dollars in bonded debt, using up available tax revenue and unable to cover interest or principal payments. When the economic collapse severely reduced tax collections, the city became unable to honor its bond commitments.^[118] The following years brought Key West's largest economic strife; by 1934, historianStuart McIver described the island as among "the poorest cities in America",^[119] as roughly three-quarters of 11,000 residents were receiving government financial aid,^[120] and its per capita monthly income dropped to less than $7.00.^[121] In July the same year, GovernorDavid Sholtz declared a state of emergency in Key West and put the city under the control of theFederal Emergency Relief Administration (FERA). He appointed the head of head of the Federal Emergency Relief Administration for the Southeastern United States, Julius F. Stone Jr., to oversee the city’s recovery efforts.^[122] Stone led the Key West Administration, a local body tasked with managing relief and redevelopment funded by federal allocations (approximately $1 million for the first 18 months).^[123]

Ernest Hemingway and his wifePauline Pfeiffer moved to Key West in 1928 inhome 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'scarriage 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-fictionGreen 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 1970posthumous 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.^[124] In 1937, he publishedTo Have and Have Not, written and set largely in Key West inside his home on Whitehead Street.Film adaptations, includingTo Have and Have Not (1944) andThe Rose Tattoo (1955), set in Key West soon earned the island's reputation as an artistic haven.^[124]

PlaywrightTennessee Williams first visited Key West in 1941, and eight years later, bought a home on 1431 Duncan Street in 1949. He stayed in the Key West property intermittently for 30 years until his death in 1983.^[125] Before purchasing the home, Williams worked from a succession of guest houses on the island, the La Concha Hotel, where he reportedly completed an early manuscript forA Streetcar Named Desire (1947) titled "Poker Night", and eventually wrote from storage shed studio in his Duncan Street home which he referred to as “the madhouse.”^[126] The honorary Tennessee Williams Fine Arts Center (later known as Tennessee Williams Theater) was opened on the island in 1980 with a premiere of Williams' play,Will Mr. Merriweather Return From Memphis?

With the onset ofWorld War II, more than 14,000 ships were brought into theisland's harbor; an almost doubling population occurred with arrival soldiers, sailors,laborers, and tourists.^[127]German U-boat operations occurred so close to Key West throughout the 1940s that locals often reported witnessing the burning wreckage ofallied cargo and military freighters from the island's shore.^[128]

"Meachum Field "(located in what is now known asKey West International Airport) was constructed as an additionalsatellite facility in 1940 to supportblimps runninganti-submarine patrols. In the same year, personnel from the Atlantic Fleet Sound School inNew London, Connecticut, were transferred to the Naval Station, Key West, to create theFleet Sonar School in theTruman Annex, tasked with trainingsonar operators to wage anti-submarine warfare againstGerman hostiles.^[129] Following the end of the World War II, operations atSubmarine Squadron 4 were transferred fromPearl Harbor to Key West in August 1945 as part of theU.S. Atlantic Fleet. The squadron was assigned commanding officers, Captains Edward S. Hutchinson and Lawrence Randall Daspit, respectively.^[130] The base was equipped with a fleet of oneFulton-class submarine tender, theUSS Howard W. Gilmore (AS-16), oneChanticleer-class submarine rescue ship, theUSSPetrel (ASR-14), aBalao-class submarine, theUSS Clamagore (SS-343), which served as the squadrons flagship from January 1946 to 1 August, 1959.^[131]

Following theJapanese surprise attack on the Pacific Fleet inPearl Harbor in 1942, wartime efforts in Key West were immediately resumed with the United States' entry into World War II. Only four days after the U.S. declared war onJapan on 12 December, 1942,OperationPaukenschlag, commanded byKarl Doenitz, was ordered byAdolf Hitler to begin an extensive U-boat campaign within the American coasts, a large portion of which occurred offshore Key West.Blackouts were frequently imposed by the Navy in order to prevent warships from being identified. A practice blackout conducted on 11 January, 1942, formed a 300-mile-long stretch of darkness fromStuart, Florida, to Key West along the Florida coastline.^[132] On 6 February, 1942, theGulf Sea Frontier (GSF), a U.S. Navy command tasked with defending theStraits of Florida and the Gulf of Mexico, was headquartered in Key West. On the night of 18 July, 1943, aK-74 navy blimp engaged in battle with aU-134 German submarine forty miles southwest of Key West.^{[133][134][135]}

As relations between theU.S. and the Soviet Union deteriorated with the beginning of theCold War, PresidentHarry S. Truman made 11 trips to Key West to organize military defense plans while staying at the Little White House.^[136] In March 1948, Truman met with the Chiefs of the Armed Forces and theDepartment of Defense in Key West to discuss military fortification plans, known as theKey West Agreement. The agreement gave the U.S. Navy,Army, andAir force in increase of control over their aviation assets for reconnaissance, medical evacuation, and other tactical functions for the island's defense.^[137]

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 asHomestead Air Force Base, Opa-Locka Marine Air Station, and the various U.S. Navy facilities in Key West.^[138] Throughout the 1950s, more than 20,000 naval personnel and over 3,000 sonar operators were trained in Key West. Important factors such as the island's advantageous water and climate conditions allowed for submarine operations to be conducted year round with minimal cancellations; Key West's stable water temperatures made sonar conditionals fairly predictable.^[139]

AfterSoviet nuclear missile sites were discovered in Cuba on 15 October, 1962, large numbers of troops and aircraft quickly arrived in Key West, and naval destroyers and submarines stationed in the harbor were dispatched out to sea. Within just a few days, Key West’s military population surged from roughly 3,000 to 12,000 as U.S. forces mobilized in response to the crisis. On 22 October, President John F. Kennedy announced a naval and air “quarantine” of Cuba to prevent further delivery of Soviet missiles. During the height of the Cuban Missile Crisis, Key West transformed into a heavily fortified military zone. Army units reinforced the shoreline withbarbed-wire and sandbag barricades, machine gun emplacements, and sixHawk missileantiaircraft batteries. Marines secured the perimeter while additional troops guarded bridges and critical infrastructure across the Keys to prevent sabotage. The historic Casa Marina Hotel was repurposed as an Army command post and housed approximately 500 soldiers. Meanwhile, Air Force, Navy, and Marine aircraft conducted hundreds of sorties from the nearby Boca Chica Naval Air Station and later from Key West International Airport, maintaining air surveillance and readiness throughout the crisis. After the naval and air quarantine of Cuba was lifted on 20 November, President John F. Kennedy and the Joint Chiefs of Staff convened at the Key West Naval Station, marking the first time such a high-level meeting occurred outside of Washington.^[140]

MusicianJimmy Buffett first visited Key West in November 1971 with singer-songwriterJerry Jeff Walker, known for his hit"Mr. Bojangles," and Walker’s partner Teresa "Murphy" Clark. The two had previously offered Buffett shelter in their open-air home inCoconut Grove after he leftNashville, Tennessee, seeking escape from both its climate and music industry pressures. At the time, the 25-year-old Buffett was recovering from the recent end of his marriage to his first wife and series of professional setbacks in Nashville.^[141] Walker and Clark, hoping to lift his spirits, invited him to Key West onbusking trip. Buffett enjoyed the island so much that he decided to move there in the spring of 1972.^[142][143] By that time, Key West had become a popular destination for numerous writers, actors, and musicians. Buffett rented a second-floor apartment, which he eventually loaned to journalistHunter S. Thompson.^[144] WriterThomas McGuane, who would later become Buffett’s brother-in-law, moved to Key West around 1970 with his then-wife, Becky, and their son.^[145] McGuane and fellow writerJim Harrison, together with painterRussell Chatham,Richard Brautigan, and French sportsman Guy de la Valdène, formed a close inner-circle in Key West during the 1970s. They often spent their days fishing and their evenings socializing in the local bar scene.^[146][147] Among one of the most popular haunts frequented by the local artists in Key West was the hotel-room-turned-bar called the Chart Room on Duval Street.^[148] Writer and later bartender at the Chart Room,Tom Corcoran, reportedly served Jimmy Buffett his first beer in Key West at the bar, where Buffett also performed for local patrons including musicianJim Croce, Thompson, McGuane, Walker, and Corcoran himself.^[149][150]

But there’s a whole wave of people coming in thinking ‘This is the greatest place I’ve ever been.’ The only thing that has really changed from the standpoint of young artists is that it’s not a cheap place anymore. I was talking to somebody that said there’s a problem down there with young people stealing the sails off sailboats so they’d have something to sleep under. But for the department of tourism in Florida, Key West still gets more inquiries than any other place in Florida exceptDisneyland.^[151]

An informalsecession from the United States occurred in 1982 in Key West in response to aUnited States Border Patrol roadblock and inspection point onUS 1. Numerous protests were sparked by the lack of accessibility into theCard Sound Bridge within the merger ofMonroe County Road 905A/Miami-Dade County Road 905A where a Border Patrol checkpoint had been performing anarcotics andillegal immigrant search.^[152] After several failed complaints by the Key West City Council claiming that the roadblock would damage the island's tourism industry, MayorDennis Wardlow and the council declared Key West as an independentmicronation on 23 April, 1982.^[153]

In January 2005, former presidentBill Clinton and his wife, then SenatorHillary 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 sinceJohn 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.^[154] 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 presidentWilliam Howard Taft in 1912.^[155]

In 2001, aninternational summit was held by formerSecretary of state,Colin Powell, in the Little White House. As of 2025^[update], several items from President Truman’s time in office remain on display on his desk in the museum, including his briefcase, books, telephone, and the “The Buck Stops Here” sign. Several landmarks in theKey West Historic District were added in the 21st century. Expanded in 1983 as a registeredU.S. Historic district, the district includes the historicSloppy Joe's Bar, added to theU.S. National Register of Historic Places in 2006.^[156] TheBasilica of St. Mary Star of the Sea, added to the Register of Historic Place in 1971, was raised a minor basilica byPope Benedict XVI on 11 February, 2012. TheWestern Union, berthed at theKey West Bight Historic Seaport, underwent restoration work in 2008 as part of theSecretary of the Interior's Standard for Historic Vessel Preservation Projects. In 2016, theSouthernmost House historic mansion was inducted into the Historic Hotels of America program.^[157]

On 24 October, 2005,Hurricane Wilma made landfall on Key West as aCategory 3tropical cyclone.^[158] The 12th hurricane of the2005 cyclone season, Hurricane Wilma brought the higheststorm surge observed in the Florida Keys since the 1965Hurricane Betsy. The island's first surge occurred at 2:30 am and reached heights of 5–6 ft (1.5–1.8 m) abovemean sea level (MSL). The runway complex at Key West International Airport was temporarilyinundated by six inches ofseawater on the Atlantic coast of the island and sustained the highest recordedwind 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 theGulf Coast, Key West's Old Town neighborhoods experienced heavy inundation.^[159] Key West sustained roughly $100 million in damages with roughly sixty percent of the homes being flooded.^[160]

A vote was approved to add three amendments to the City Charter in 2020 that prohibited large cruise ships into thePort of Key West, sponsored Key West Committee for Safer, Cleaner Ships.^[161] The Port's cruise ship dock was originally opened in 1984 inMallory Square and was met with disapproval by citizens that it would disrupt sunset watching on the square. In 2021, theFlorida State Legislature overturned the amendments. In March 2024,Florida GovernorRon DeSantis approved renovation plans for Pier B, a project in which to service larger ships in the harbor.^[162]

Thefishing industry was the center of Key West's economy throughout the island's history.^[163] Throughout much of the 19th and 20th centuries, Key West supplied eighty percent of all turtle products in the United States.^[164] Turtle fishing off of Key West first appeared in records of Ponce de Leon's voyage 68 miles off of the island to theDry Tortugas in 1513, in which his crew reportedly caught 160Green sea turtles to satisfy their supply offood rations. The presence of sea turtles soon contributed to the island's nameLas Tortugas, Spanish for "the turtles". The turtles, extracted for meat,eggs, andsoup, became a lucrative resource for early fishermen in Key West. Sea turtles in the island's waters were captured using small enclosures used astraps made from wooden orconcrete pillars situated near Key West's harbors where they could be quickly processed in nearby canning buildings.^[165]Soup canning, made often from the green pigment of theturtle 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 tooverfishing. 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 23 June, 1994, Key West's historic turtle Soup Cannery Buildings were added to the U.S. National Register of Historic Places.^[166]

Key West'swrecking industry contributed the island's wealthiest periods throughout much of the 19th century.^[167]Shipwrecks became a common occurrence in the Florida Keys with vessels from theOld World running aground in the region's shallowreefs. Indigenous Natives in Key West were often employed by local industries tosalvage cargo from wreckedmerchant vessels during the early 17th century, including a major salvaging by natives of the Spanish Fleet wrecked off of theMarquesas Keys in 1622.Salvaging of the remains of theNuestra Señora de Atocha, wrecked off of Key West on 6 September 1622, lasted for a duration of eight years by hired natives.^[168] On 4 July, 1823, Key West's wrecking act, developed by the legislative council of theTerritory of Florida, contained 14 sections ruling that salvagers were required to bring wrecked property into theUnited States territory and "report it to the nearestjustice of the peace".^[169]

As a result of the newly formed wrecking industry, thePensacola 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 3 March, 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"^[170] was sold in Key West with the establishment of Superior Court in Key West ofmaritime andadmiralty jurisdiction mandating that all Florida Keys wrecking property be taken to Key West.^[171]

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 toYbor City inTampa.^[172] 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 ofKey West's reefs in the 19th century, enabling the production of roughly 2,000 tons ofsponge 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.^[173]

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