Historic Key West

DATE First became a Spanish possession in 1565; sold to an American in 1822

SIGNIFICANCE: Current seat of Monroe County, Florida, Key West has a long and colorful history of economic, demographic, and military importance. Today, the city is probably best known as the 1930s home of Ernest Hemingway, who used Key West and Key West–inspired tropical seaside cities as the backdrop for several of his novels and short stories. The city’s population of approximately thirty thousand depends primarily upon fishing and tourism for economic sustenance. Key West’s Old Town is a well-preserved historic district.

LOCALE: The southernmost settlement in the continental United States, located approximately 100 miles west-southwest from mainland Florida on a coral island slightly less than 8 square miles in total area; often described as the westernmost of the chain of Florida Keys, but in reality only the westernmost inhabited island of the chain

Due to its strategic location between the Gulf of Mexico and the Atlantic Ocean, only 90 miles from Cuba, Key West has seen more than its share of migrations, revolutions, conquests, and periods of prosperity. The city has lived under Spanish, British, and American flags, and its population and culture reflect a mix of Cuban, European, Caribbean, African, and mainstream American influences. Key West politics have run the gamut from socialist to libertarian, and the city has been both the wealthiest and the poorest in Florida. Through it all, the residents of Key West—historic and modern—have earned a reputation for taking it all in stride.

The Old Town Historic District of Key West, a 1-square-mile community located along Duval Street from the Atlantic to the Gulf, contains most of the city’s historic sites. Fire destroyed approximately half of Key West in 1886, and serious efforts at historic preservation came in fits and starts between 1934 and the 1970s. A remarkably large portion of the city’s history has been retained, however; 2,000 of the 3,100 buildings within the historic district are considered to be historically significant. Visitors to the city today will find plenty of important relics of Key West’s freewheeling past tucked into the urban fabric amid the modern resorts and tourist traps that have become the island’s economic lifeblood.

Early History

Key West was probably first sighted by Europeans in 1513 when Spanish explorer Juan Ponce de Léon landed at what is now St. Augustine, Florida, in his quest for the Fountain of Youth. Sailing southward along the Atlantic coast of Florida, Ponce de Léon recorded passing through the Straits of Florida between the Florida Keys and Cuba, although he made no specific mention of Key West in his journals.

For the next 250 years, Spanish adventurers and entrepreneurs traded and traveled throughout mainland Florida and the Keys despite the territory’s changes in ownership. Florida became a solid Spanish possession in 1565, after Spanish soldiers decimated a settlement of French Huguenots in northern Florida and established the city of St. Augustine, the oldest city in the United States. The Spanish named what is now Key West Cayo Hueso (island of bones), after the large quantity of human bones they found strewn about the island. Local legend says that they were the remains of the Calusa people, an unlucky tribe pursued by its enemies across the Keys and slaughtered when there was nowhere left to run.

Notoriety

Key West’s rough-and-tumble reputation was born during this early period. With treacherous coral reefs and unpredictable currents, the Keys provided both navigational hazards and plenty of places to hide. The thousands of islands in the 192-mile chain were favorites of the pirates who roamed the Straits of Florida in the eighteenth and early nineteenth centuries, preying upon merchant ships or on the Spanish fleet as it returned from South America, sometimes dangerously overladen with treasure. The pirates’ practice of looting ships in trouble was eventually turned into a legitimate business by later generations of islanders, who made “wrecking”—salvaging valuables from shipwrecks—a legal and lucrative enterprise. The legendary pirates Blackbeard and Jean Lafitte were among the motley crew who infested the Keys during this period.

Florida remained in Spanish hands until 1763, when British victory in the French and Indian War forced Spain to acquiesce to British demands for the territory. The territory once again found itself in Spanish hands in 1783, following the American Revolution, but continued to be used by Great Britain for covert activities against the newly founded United States from 1783 through the War of 1812.

Cession to the United States

In 1815 the colonial governor of East Florida, Juan José de Estrada, granted Key West to a Spanish artillery officer named Juan Pablo Salas, whose service to the Crown at St. Augustine merited a sizable reward. Florida was ceded to the United States in 1819, but Salas managed to maintain ownership of his island until 1822, when he sold it for two thousand dollars to an American named John W. Simonton, thereby making the island American territory.

Later that year the US government sent Commodore David D. Porter, with his famed “mosquito fleet” of the West Indies Squadron, to rid the Keys of the pirates who had held them for so long. Following his mission a naval depot was established on Key West, beginning an American military presence on the island that remained unbroken until 1974, when budget cutbacks forced closure of the naval base. A small naval air station is still based on a nearby Key.

The military was destined to play a major role in the growth of Key West. There are three fortifications on the island alone: Fort Zachary Taylor, East Martello Tower, and West Martello Tower. Located on the island’s west side, Fort Taylor was constructed between 1854 and 1866 and served as an important naval base during the Civil War, enabling the Union navy, which controlled the island throughout the war, to mount a successful blockade of Confederate ships—one that may have reduced the length of the war by as much as a year. The towers, begun in 1861, were never completed because advances in military equipment made them obsolete almost immediately. Today, Fort Taylor is both a Florida State Park and a National Historic Landmark, and the towers, east and west, serve as home to an art gallery and the Key West Garden Club, respectively.

“Fort Forgotten”

Unused and buried under tons of sand, Fort Taylor was once dubbed “Fort Forgotten” by islanders and was once considered a possible site for a sewage treatment plant. In 1968, however, local resident Howard England, a historian and civil architect for the Key West naval base, waged a grassroots preservation campaign to save the historically important site. With the help of his sons and other volunteers, England began to dig, eventually uncovering most of the south side of the fort and excavating thousands of weapons and other artifacts from the Civil War. The fort is now considered to be one of the most important Civil War sites in the nation.

Although located in the Dry Tortugas, a small group of islands located 70 miles west of Key West at the very end of the Keys, Fort Jefferson, dubbed the “Gibraltar of the Gulf,” was conceived as part of the same military buildup that had fortified Key West. Begun in 1846, Fort Jefferson was built on Garden Key and is well protected by a cluster of seven hazardous coral reefs and a large population of shark and barracuda. Intended for grand military purposes, Fort Jefferson managed only to serve as a prison during and immediately following the Civil War. Its most famous prisoner was Dr. Samuel Mudd, who treated Abraham Lincoln’s assassin, John Wilkes Booth. The island, which was designated Fort Jefferson National Monument in 1935 and was added to the National Register of Historic Places in 1970, is now a sanctuary for wild birds and a wide variety of marine life.

Early Nineteenth Century Growth

After Key West had been secured by Commodore Porter, it began to attract its unique population. Previously home to Spaniards, Britons, and (probably) Calusa, the island experienced unprecedented growth in the 1820s and 1830s, bringing together the varied lot of entrepreneurs, pleasure-seekers, and eccentrics who continue to populate the island today.

First to settle in the new US territory were New Englanders, Virginians, and South Carolinians in search of a new and different way of life. Joining them were pro-British Tories who had fled to the British-ruled Bahamas during the American Revolution. These settlers incorporated the modern city of Key West in 1828.

The “Conchs”

Along with these settlers of easily determined lineage came the people who came to be known as “conchs” (konks), after the large shellfish that forms an important part of the Key West diet. The original conchs were descended from English Cockney fishermen who plied their trade throughout the American colonies and landed in Key West following the Revolutionary War.

The story of the conchs began in 1646 when Captain William Sayle, a British territorial governor from Bermuda, claimed to have been granted, by Parliament no less, his very own island in the Bahamas. Although no record of this grant has ever been found, Sayle and his band of self-proclaimed Eleutheran Adventurers sailed to the Bahamas to found a colony where “every man might enjoy his own opinion or religion without control or question.”

Their destination was an island that early Spanish explorers had called Cigateo. They changed the name to Eleutheria, which later became Eleuthera. The island’s politics were laissez-faire from the very beginning, and it soon became a haven for runaway slaves, revolutionaries, and religious zealots, all of whom found a niche on Eleuthera. One legend says that the conchs got their name when they said that they would rather “eat conch” than pay the taxes levied against them by the British Crown. Why this was regarded as such an outlandish statement is not explained; conch has since become a staple of the Key West diet.

When Britain gained control of Florida in 1763, large numbers of Britons, largely Cockneys seeking a better life, moved to the new colony, only to be forced out in 1783 when Florida was returned to Spain. Having spent a generation in the tropics, most of the settlers moved to other parts of the West Indies, including Eleuthera. Eventually, many conchs came to the Florida Keys, and these settlers were to play a vital role in the development of Key West.

Wrecking

The first major industry established by the conchs on Key West was “wrecking,” or salvaging shipwrecks. The same navigational hazards that had given generations of pirates places to hide continued to wreak havoc on commercial shipping throughout the Keys and the Straits of Florida, creating a lucrative business out of the misfortune of others. In fact, some people believed that many a ship had been lured to its doom by overzealous wreckers eager to make some easy money.

Wrecking was fully sanctioned by law. In 1828 the United States established an official superior court on the island to handle the day-to-day legal affairs of the growing populace. One of the court’s most prolific functions was issuing salvage licenses to professional wreckers. The court also ruled that salvage rights to the cargo of a wrecked ship belonged to whoever got there first. Therefore, competition was keen to be the first to reach a new wreck, leading many wreckers to head to sea in the same storms that had created the wrecks they intended to salvage. Such practices led to many disputes among the wreckers, which also had to be ironed out by the court.

Wrecking had always been a profitable business in the West Indies, but the rapid growth of Key West, not to mention its proximity to so many treacherous waterways, made the island the capital of the region’s wrecking business almost overnight. Wreckers from Nassau and Havana set up shop in Key West. In particularly good years (or particularly bad, depending upon one’s point of view), bidders spent more than $1 million on items salvaged by the wreckers. In 1846 alone, wreckers recovered $1.6 million worth of goods. Wrecking continued to be a major industry until 1852, when a system of lighthouses and blinking reef lights made sailing the Keys much safer.

Prosperity

In the 1830s Key West was the wealthiest city per capita in the United States. The sudden and massive influx of industrious entrepreneurs in the 1820s had created a boomtown on what had been an irregularly populated chunk of coral with no obvious natural resources. In fact, resources were there, but like wrecks they needed to be exploited properly.

One hidden resource was the vast quantity of natural sponge growing in the waters around the island. Conchs dominated this industry for decades, developing an ingenious method whereby they hooked sponges from depths of up to 60 feet without even venturing into the water. A small community of Greek spongers threatened the conchs’ share of the trade by diving directly to the sponges, using weighted diving shoes that allowed them to stay longer on the bottom and harvest several sponges at once. The conchs clung to their old method, believing that the diving shoes worn by the Greeks harmed the sponge beds. At one point, conchs burned the boats of the Greek divers, and the Florida legislature eventually banned diving for sponges in the Keys, leaving the conchs to their tried-and-true method. A case of blight nearly destroyed the sponge beds in 1940 and several times thereafter, quickly shrinking the local sponging industry.

Civil War Years

Key West was held by Union forces for the duration of the Civil War, despite its claim as the southernmost city in the continental United States. Even so, sentiment among the islanders ran highly in favor of the Confederacy. The islanders’ independent streak was thoroughly tested during this period, for Key West served as an important base for blockade runners loyal to the Confederacy. True, the presence of Union naval forces on the island made things difficult, but many of the conchs challenged the blockade anyway. Scores of blockade runners were captured and tried in Key West during the war.

The Civil War ended in 1865, but another war, the Ten Years' War in Cuba, began in 1868, sending a massive wave of Cuban immigrants into Key West and adding another layer to the Key West demographic. By 1868, Cubans were already a mixed lot, with Spanish, African, and indigenous influences. They brought with them their religions, their customs and cuisines, and, most importantly for Key West, their legendary love of good cigars.

Cigar Industry

The first cigar factory in Key West was established in 1831 by William H. Wall. In most cases, the term “factory” is misleading, as the chinchares (called “buckeyes” by Americans) were mostly small, home-based businesses. The first Cubans to come to Key West in 1868 established their own chinchares, and in 1869 a Spaniard named Vicente Martinez Ybor, owner of El Principe de Gales (prince of Wales) cigar factory in Havana, moved his operations to Key West as a means of escaping persecution by Spanish authorities unhappy with his sympathy for the independence movement.

Ybor’s move was followed by the influx of thousands of other cigar manufacturers from Cuba, and they soon turned Key West into one of the world’s most important cigar-manufacturing centers. At first, manufacturers returned to Cuba after making some money in Key West, but it did not take long for them to change their tactics and begin to return to Cuba only long enough to prepare to take their families back to Key West. In addition to the greater personal freedom gained by establishing residence in the United States, the Cubans also profited from not having to pay import duties on their cigars and from freedom from La Liga, the Cuban cigar manufacturing union.

The cigar workers, however, had different ideas about the desirability of unions. Shortly after the industry was established on the island, so were unions, becoming the first unions in the state of Florida. Inevitably, there was a major strike, called in 1889 to demand an increase in wages. The strikers won their raise early in 1890, but struck again in 1894 when their employers refused to stop importing labor from elsewhere. By the turn of the century the cigar business had almost ceased to exist in Key West, having transferred en masse to Tampa, a migration that had begun in 1886 following the devastating fire that destroyed almost half of the island and a large portion of the cigar industry. Still, the height of the Key West cigar business was achieved in 1890, when twelve thousand workers (of a total population of eighteen thousand) produced one hundred million cigars, making Key West the undisputed cigar manufacturing center of the United States.

Cuba’s Revolutionary Movement

While the first Cuban revolutionary movement had been unsuccessful, Key West served as a handy staging area for the plotters of the subsequent Cuban War of Independence in the 1890s. The leader of the revolution, José Martí y Pérez, established residence on the island during the cigar industry boom. In conjunction with the Junta Central Revolucionaria de Nueva York (Central revolutionary committee of New York), Martí planned the Partido Revolucionario Cubano (Cuban Revolutionary Party). On April 14, 1895, he set forth from Key West to Cuba, accompanied by Cuban General Máximo Gómez y Báez and a small army, thus beginning the revolution. During the fighting that followed, Key West provided a safe haven not only for refugees from the war but also for the obligatory horde of journalists assigned to cover it. When the Spanish-American War broke out in 1898, Key West served as an important US naval base.

Building a Land Route

Key West’s relative isolation and inaccessibility had always been its greatest blessing and its greatest curse. Isolation allowed the islanders to create a distinct society of their own with little interference from the outside, but the same isolation also forced islanders to take what they could get. Not just any industry could establish itself in Key West. All travel and commerce had to be done by boat, and relatively few people could get into Key West without booking passage with somebody else. As the island prospered, it became apparent that a land route to the island was needed.

In terms of turn-of-the-century technology, such an engineering feat was without peer, and it was left to a very wealthy visionary to make the dream a reality. Industrialist Henry M. Flagler, one of John D. Rockefeller’s partners in Standard Oil, proposed extending the Florida East Coast Railway across the Keys from the mainland all the way to Key West. Skeptics immediately dubbed this plan “Flagler’s Folly,” to which Flagler responded, “All you have to do is to build one concrete arch, and then another, and pretty soon you’ll find yourself in Key West.”

Construction on the railway began in 1906 but was quickly stalled by a hurricane that killed one hundred thirty workers. Flagler insisted that work continue, and in 1909 another hurricane destroyed 40 miles of already-laid track. On January 22, 1912, the Overseas Extension finally opened. The railway stretched a 100 miles, hopping from Key to Key and covering 25 miles on land and 75 miles over water at a final cost of fifty million dollars and seven hundred lives.

World War I vastly increased the amount of military activity on the island, with surface ships, submarines and airplanes all stationed there. The island’s strategic location on the Straits was crucial to the safety of the Gulf of Mexico. Inventor Thomas Edison carried out experiments with the first depth charges while in the Keys.

Prohibition and Depression

Prohibition, enacted in 1919, was roundly ignored in Key West. With Cuba, one of the world’s largest producers of rum, only 90 miles away, illegal liquor was readily available on the island and restaurant and cafe owners made only the weakest of attempts to hide their patrons’ activities from local authorities. Prohibition was still in force in 1931 when Ernest Hemingway, a notable drinker, first took up residence on the island. Rum-running became something of a sport in Key West, with the activities of bootleggers and US authorities adding still more color to the island’s image.

The Great Depression took an especially heavy toll on Key West. In 1934, the city was officially bankrupt and approximately 80 percent of its residents were on some form of government relief. In July, 1934, the Key West City Council passed a resolution petitioning the governor of Florida to declare a state of emergency on the island. In response to this request, the Florida Emergency Relief Administration was instructed to find a way to assist the economically shattered community. As with most other ideas, the philosophy of the New Deal was destined to take a peculiar twist in Key West.

The answer to the problems of Key West, the state surmised, lay in its potential as an upscale resort town—a fitting rival to Havana, Nassau, and Bermuda. Buildings were renovated, beaches created, and hotels reopened. Residents contributed some two million hours of labor to clean and beautify the city’s streets and public areas. As frivolous as it may have seemed initially, the experiment became a huge success, reinvigorating the local economy and paving the way for the tourist development that has grown on the island ever since. The program became regarded as one of the most interesting experiments in community planning ever devised, and the Florida Emergency Relief Administration quickly transplanted unemployed artists to the island and provided them with the funding necessary to further enhance Key West’s appeal to tourists.

In 1935, disaster struck Key West when a Labor Day hurricane swept through the Keys, sparing Key West, but ruining much of the railroad that had done so much to broaden the nature of life on the small island. The railway company, already deeply in debt, abandoned what remained of the extension and moved its sea ferry operation to the Atlantic Coast, near Fort Lauderdale. Key West’s local fishing industry, lacking transportation to the markets of the mainland, was destroyed.

In 1936 the railway’s right-of-way was taken over by the Monroe County Toll Bridge Commission and construction began on an extension of US Route 1, to be called the Overseas Highway. Utilizing a combination of new bridges and some left over from the railroad, the highway opened to the public in 1938 and remains in service to this day.

World War II and the Conch Republic

World War II saw another military buildup on the island, when a seaplane base, Boca Chica Air Station, and a naval hospital were established at Key West. Key West’s military history is reflected not only in the physical evidence of its former presence, but also by the presence of a large number of retired military personnel on the island—yet another demographic added to the Key West mix.

The peculiar character of the residents of Key West has been exaggerated, as with most such stereotypes, but they are undoubtedly the keepers of a genuinely distinctive lifestyle. For example, in 1982, when US government authorities began a major campaign to curtail drug smuggling in the Straits of Florida, certain conchs responded by declaring Key West the “Conch Republic” and seceding from the Union. Naturally, the Conch Republic quickly collapsed, but not before making a last-minute plea for “foreign aid.” Reminders of the short-lived republic can be seen in Key West today on such items as T-shirts and other souvenirs.

Architecture as a Key to History

Simply by looking at the architecture, visitors to Old Town will quickly understand the varied demographics that built the city. Primarily one-and-a-half- and two-and-a-half-story frame buildings called Conch houses, the structures drew their inspiration from Spanish, Victorian, and Creole designs. Very few of the older buildings on Key West were designed by trained architects, but were built by self-taught “carpenter architects” who adapted their designs to suit their own tastes. Many buildings are decorated with carved pieces of wood salvaged from wrecked ships, for example. Interior furnishings are equally eclectic, as everything in Key West came from somewhere else.

The Conch houses are ideally adapted to the rigors of life on Key West. Constructed entirely with such archaic techniques as dovetail joints, the fact that the buildings can withstand hurricane-force winds is borne out simply by the fact that so many of them have been standing since the early 1800s. Most buildings are equipped with extra-thick shutters to provide protection in high winds and all utilize cisterns in which to catch rainwater, usually from a pitched roof.

Literary Associations

Many notable writers have spent part of their careers in Key West, both deriving inspiration from and adding to the eccentric character of the island. The most famous of these was Ernest Hemingway, who wrote A Farewell to Arms and other works while in residence between 1931 and 1940. Key West also provided the setting for some of Hemingway’s short stories and novels, including To Have and Have Not. Gore Vidal, Robert Frost, Wallace Stevens, and Kurt Vonnegut are also associated with Key West, as is Tennessee Williams, who lived at 1431 Duncan Street from 1949 until his death in 1983. Hemingway’s Spanish colonial house, at 907 Whitehead Street, has been declared a National Historic Landmark. The grounds of the house, officially called the Ernest Hemingway Home and Museum, are still home to many polydactyl (six-toed) cats, some of whom are directly descended from Hemingway’s own cats.

Other notable historic buildings include Amsterdam's Curry Mansion Inn, an elaborate home constructed in 1869 by successful wrecker and self-made millionaire William Curry, which offers rooms to rent as well as daily tours; and Audubon House and Tropical Gardens, located at 205 Whitehead Street. Built in the early 1800s for one of Key West’s most prominent wreckers, Captain John H. Geiger, Audubon House was restored in commemoration of its use in several portrayals of the gray kingbird and white-crowned pigeon painted by naturalist John James Audubon when he visited Key West in 1832.

Museums

Key West is also home to many fine museums dedicated to the preservation of the island’s unique history. Among these are the Mel Fisher Maritime Museum, featuring artifacts salvaged from a Spanish treasure galleon that sank nearby in 1622; the Key West Shipwreck Museum, featuring photographs and other artifacts from the wrecking era; the Martello Gallery–Key West Art and Historical Museum, located in the East Martello Tower and featuring information about the tower, the city’s sponge and cigar industries, and an art gallery; and the Lighthouse Tower and Keeper's Quarters museum, which contains artifacts related to the Key West lighthouse and those who lived there over the years; the Tennessee Williams Museum, expanded from a 2013 exhibit, which opened at 513 Truman Avenue in late 2017; and the museum at Fort Zachary Taylor Historic State Park, a major repository of Civil War artifacts.

Bibliography

Born, George Walter. Historic Florida Keys: An Illustrated History of Key West & the Keys. Historical Publishing Network, 2003.

Born, George Walter. Preserving Paradise: The Architectural Heritage and History of the Florida Keys. History Press, 2006.

"Florida Keys History Reading Room." Keys Historeum, edited by Jerry Wilkinson, Historical Preservation Society of the Upper Keys, www.keyshistory.org/cmreadingroom.html. Accessed 28 May 2024.

Keith, June. June Keith's Key West and the Florida Keys. 5th ed., Palm Island Press, 2014.

Kennedy, Stetson. Palmetto Country. Duell, Sloan & Pearce, 1942. Provides a wealth of historical and anecdotal information on the entire region surrounding Key West, including mainland Florida, the Bahamas, and Cuba. Short on hard facts but long on illuminating stories.

Kinser, Joshua Lawrence. Florida Keys: Including Miami & the Everglades. 3rd ed., Avalon Travel, 2017.

Langley, Wright, and Joan Langley. Key West and the Spanish-American War. Langley Press, 1998. Describes the role of Key West and the rest of Florida of the Spanish-American War of 1898. Illustrated, including maps.

"Literary Landmarks Showcase Key West’s Creative Heritage." The Florida Keys & Key West, Monroe County Tourist Development Council, 8 Jan. 2018, www.fla-keys.com/news/article/8683/. Accessed 28 May 2024.

Works Progress Administration, Federal Writers’ Project. Florida: A Guide to the Southernmost State. 1939. Scholarly Press, 1976. A very well-researched, straightforward guide.

Works Progress Administration, State of Florida, Writers’ Program, compilers. A Guide to Key West. Hastings House, 1941. HathiTrust Digital Library, catalog.hathitrust.org/Record/000197826. Accessed 10 May. 2018.