Florida: Key West Summary

  • Last updated on November 10, 2022

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 1930’s 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.

Site Office

Historic Florida Keys Preservation Board

510 Greene Street

Key West, FL 33040

ph.: (305) 292-6718

fax: (305) 293-6348

Due to its strategic location between the Gulf of Mexico and the Atlantic Ocean, only ninety 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 one-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 1970’s. 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 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, meaning “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 Indians, an unlucky tribe pursued by its enemies across the Keys and slaughtered when there was nowhere left to run.


Key West’s rough-and-tumble reputation was born during this 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 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

The king of Spain in 1815 granted Key West to a Spanish artillery officer named Juan Pablo Salas, whose service to the Crown at St. Augustine merited a sizeable 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 U.S. 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, including 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, when the Union navy, which controlled the island throughout the war, mounted a successful blockade of Confederate ships, which some say 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 a National Park 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 seventy 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 is now a National Monument and 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) Indians, the island experienced unprecedented growth in the 1820’s and 1830’s, bringing together the varied lot of entrepreneurs, pleasure-seekers, and eccentrics who continue to populate the island today.

First to settle in the new U.S. 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. (Today, all Key Westers are known as conchs. Residents of the island not born there are known as “freshwater conchs” until they have lived there for seven years, at which time they become “honorary conchs.”) 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 a band of so-called 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 named Segatoo by Christopher Columbus. They changed the name to Eleuthera, but the island eventually became known as Abaco. 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 Abaco. One legend says that the conchs got their name when they said that they would rather “eat conchs” 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 Abaco. Eventually, many conchs came to the Florida Keys, and these settlers were to play a vital role in the development of Key West.


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.


In the 1830’s Key West was the wealthiest city per capita in the United States. The sudden and massive influx of industrious entrepreneurs in the 1820’s 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 sixty 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 Cuban Revolution, began in 1868, sending a massive wave of Cuban immigrants into Key West, 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 Ibor, owner of El Principe de Gales 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.

Ibor’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 War of Cuban Independence in the 1890’s. The leader of the revolution, José Martí y Pérez, established residence on the island during the cigar industry boom. In conjunction with the Central Junta, based in New York, Martí planned the Patricio Revolutionario Cubano and on April 14, 1895, set forth from Key West to Cuba accompanied by Cuban General Máximo Gómez y Báez and a small army, 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 U.S. 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 and was quickly stalled by a hurricane that killed one hundred thirty workers. Flagler insisted that work continue, and in 1909 another hurricane destroyed forty miles of already-laid track. On January 22, 1912, the Overseas Extension finally opened. The railway stretched a full one hundred miles, hopping from Key to Key and covering twenty-five miles on land and seventy-five 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 ninety 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. Rumrunning became something of a sport in Key West, with the activities of bootleggers and U.S. 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 U.S. 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 U.S. 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 1800’s. 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, Jr., 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 are still home to many six-toed cats directly descended from Hemingway’s pets.

Other notable historic buildings include Audubon House, located at 205 Whitehead Street. Built in the early 1800’s for one of Key West’s most prominent wreckers, Captain John H. Geiger, the 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.


Key West is also home to many fine museums dedicated to the preservation of the island’s unique history. Among these are Mel Fisher Maritime Heritage Society, featuring artifacts salvaged from a Spanish treasure galleon that sank nearby in 1622; the Wrecker’s Museum, featuring photographs and other artifacts from the wrecking era; the East Martello Gallery and Museum, located in the East Martello Tower and featuring information about the tower, the city’s sponge and cigar industries, and an art gallery; the Key West Lighthouse Museum, specializing in lighthouses and offering a magnificent view from the top of its 110-foot tower, erected in 1847; Fort Zachary Taylor, a major repository of Civil War artifacts; Heritage House and Robert Frost Cottage, built on the site of the first freshwater well on the island, and the home of the late poet; and Curry Mansion, an elaborate 1905 home constructed by William Curry, a successful wrecker and Florida’s first millionaire.

For Further Information

In addition to the sources below, Key West is covered in most current Florida travel guides, and the Historic Florida Keys Preservation Board can provide even the most arcane information to determined researchers. The works of Key West’s most famous resident, Ernest Hemingway, are available in various editions.

  • Federal Writers’ Project. Florida: A Guide to the Southermost State. New York: Oxford University Press, 1939. A product of the Works Progress Administration. The guide is a very well-researched, straightforward source. The WPA produced many such guides during the late 1930’s, all of which, while somewhat dated, are excellent reference sources.
  • Kennedy, Stetson. Palmetto Country. New York: Duell, Sloan and Pearce, 1942. Provides a wealth of historical and anecdotal information on the entire region surrounding Key West, including mainland Florida, the Bahamas, and Cuba. It is short on hard facts but long on illuminating stories.
  • Langley, Wright. Key West and the Spanish-American War. Key West, Fla.: Langley Press, 1998. Describes the role of Key West and the rest of Florida of the Spanish-American War of 1898. Illustrated, including maps.
Categories: History