History of Key West: From Island of Bones to Conch Republic

We admittedly know little about the earliest settlers in Key West, the Native Americans who lived here left very few remnants of their civilization.

Key West may look laid-back today—bright houses, palm trees, chickens in the streets, sunsets at Mallory Square—but behind the sunshine is a long, twisty story full of shipwrecks, pirates, brave builders, powerful storms, famous writers, and people from many cultures who made the island home.

The History of Key West is the story of how a tiny island at the very end of Florida became one of the most interesting places in the United States.

Key West History

We’ll start with the first European sightings, move through the pirate years and the era of “wrecking,” meet cigar makers and revolutionaries, ride Henry Flagler’s railroad, survive the Great Depression and World War II, and finally wave the flag of the playful “Conch Republic.”

Early Sightings and the “Island of Bones”

• 

  1513: Spanish explorer Juan Ponce de León sails past the Keys.

• 1565: Spain establishes control of Florida after founding St. Augustine.

• The Spanish name Key West Cayo Hueso (“Island of Bones”), after finding skeletal remains, possibly from the Calusa tribe.

• English settlers later misheard the name, leading to “Key West.”

The first Europeans to sail past the Florida Keys did so in 1513. That year, Spanish explorer Juan Ponce de León, one of the prolific explorers of his time, landed in what is now St. Augustine, Florida while searching for the legendary Fountain of Youth.

After exploring the northeast coast, he sailed southward and passed through the Straits of Florida, the stretch of water separating Florida from Cuba. His journals never mention Key West by name, but we know he and his crew saw the string of islands that make up the Keys.

By 1565, Spain had a firm claim to Florida. That year, Spanish soldiers destroyed a French settlement in northern Florida and founded St. Augustine, the oldest permanent European settlement in the United States.

The Spanish gave the island at the end of the Keys a name: Cayo Hueso, which means “Island of Bones.”

According to legend, when they arrived, they found the ground littered with human remains. The story says these bones belonged to the Calusa, a Native tribe who had once ruled southern Florida.

They were chased through the Keys by their enemies until they could run no farther. Trapped on the last island, they were killed, leaving their bones scattered. Whether this tale is completely true or part myth, it gave the island its haunting name.

When English speakers later came to the Keys, they misheard “Cayo Hueso.” To their ears, it sounded like “Key West.” And so the name stuck.

Even today, locals sometimes proudly use the old Spanish name—Cayo Hueso—to honor the island’s past.

Pirates, Treasure, and Wrecking

• By the 1700s, pirates like Blackbeard and Jean Lafitte terrorized ships near the Keys.

• Dangerous coral reefs caused countless shipwrecks.

• Wrecking became a legal and profitable trade — salvaging cargo from wrecked ships.

• Key West became the Wrecking Capital of the World in the mid-1800s.

By the 1700s and early 1800s, the Keys had gained a dangerous reputation.

The surrounding waters were filled with sharp coral reefs, hidden shoals, and strong currents. Ships often wrecked on these reefs, and the many small islands offered perfect hiding spots.

This made the Florida Keys a pirate’s paradise. Pirates and privateers sailed the Straits of Florida, attacking merchant vessels loaded with goods or even Spanish treasure fleets returning from South America. Famous pirates such as Blackbeard and Jean Lafitte were said to have prowled the area.

At first, the looting of shipwrecks was pure piracy. But eventually, the practice was transformed into something legal.

Islanders began the business of wrecking—salvaging valuable cargo from ships that ran aground. Wrecking became a respected (and very profitable) trade. Whoever reached a wreck first had rights to claim its cargo, and entire fortunes were built on the goods pulled from the sea.

By the mid-1800s, Key West became known as the Wrecking Capital of the World. Some years, more than a million dollars’ worth of goods were auctioned off from salvaged ships. That’s a massive fortune for the time.

Florida Changes Hands

• 1763: Spain cedes Florida to Britain.

• 1783: Spain regains Florida after the American Revolution.

• 1819: Spain cedes Florida to the U.S. in the Adams-Onís Treaty.

• 1821: On July 10, 1821, the Spanish flag was removed, and the new American flag was put in its place.

The Keys did not stay under Spanish control forever. After the French and Indian War ended in 1763, Spain was forced to hand Florida over to Britain. But British rule didn’t last long. Following the American Revolution, Spain regained Florida in 1783.

During this time, the Keys became a kind of secret playground for Great Britain. Even though the United States was now independent, the British used the islands for covert activities during the War of 1812.

It wasn’t until 1819 that Spain finally ceded Florida to the United States. This changed everything for Key West.

Becoming American

• 1815: Spain grants Key West to Juan Pablo Salas.

• 1822: John W. Simonton purchases the island.

• 1822: Commander Matthew C. Perry arrived aboard the USS Shark and claimed the island for the U.S. He declared Key West a naval reservation to help combat piracy.

In 1815, while Florida was still Spanish territory, the governor of East Florida gave Key West as a reward to a Spanish artillery officer named Juan Pablo Salas. But by 1821, Florida had officially become American territory.

Salas sold the island in 1822 to an American businessman named John W. Simonton for $2,000. That sale officially brought Key West under the United States.

The U.S. government wasted no time establishing its presence. Later that year, Commodore David Porter arrived with his West Indies Squadron, nicknamed the “mosquito fleet.”

His mission was to drive out the pirates who had controlled the Keys for decades. He succeeded, and soon after a naval base was built on Key West. This began a long history of U.S. military activity on the island—a presence that lasted, in some form, well into the 20th century.

Riding the Keys of pirates and other scoundrels was the first step in the development of Key West.

Forts and the Civil War in Key West

• Fort Zachary Taylor (1854–1866): Union stronghold during Civil War.

• East & West Martello Towers: Built as coastal defenses.

• Fort Jefferson (Dry Tortugas): Became a prison, held Dr. Samuel Mudd.

The military shaped much of Key West’s growth. Three important fortifications were built on the island: Fort Zachary Taylor, East Martello Tower, and West Martello Tower.

Fort Zachary Taylor, built between 1854 and 1866, was especially important during the Civil War. Though Key West was in the South, the Union controlled the island throughout the war.

The fort had an uneasy situation with Florida being a Confederate State, yet its location was just a short few blocks from the main city. Residents tolerated the soldiers and vice versa.

From Fort Taylor, the Union Navy blockaded Confederate ships, a move that may have shortened the war by a year.

The Martello Towers, begun in 1861, were never completed. By the time they were being built, military technology had already made them outdated. Today, East Martello is home to an art gallery, while West Martello is the headquarters of the Key West Garden Club.

One of the most fascinating stories is that of Fort Zachary Taylor. For years, it sat unused, buried under sand, and forgotten by many locals.

In fact, people once considered turning it into a sewage plant! In 1968, a local historian and civil engineer named Howard England led a campaign to save it. With volunteers, he began digging out the fort by hand.

They uncovered thousands of Civil War-era weapons and artifacts. Thanks to his efforts, the fort is now preserved as both a Florida State Park and a National Historic Landmark.

Seventy miles west of Key West sits another massive structure: Fort Jefferson in the Dry Tortugas. Started in 1846, it was called the “Gibraltar of the Gulf.”

Although planned as a powerful military base, it mostly served as a prison. Its most famous inmate was Dr. Samuel Mudd, who treated John Wilkes Booth after President Abraham Lincoln’s assassination.

Today, Fort Jefferson is part of a national park and is famous for its birdlife, coral reefs, and history. Tourists frequent the Fort by seaplane and boat charters.

Growth in the 1800s

• 

  Bahamian settlers known as Conchs arrive.

• Industries: wrecking, sponging, fishing.

• By the 1830s, Key West had become one of the wealthiest U.S. cities per capita.

Once pirates were driven away, settlers from the United States began arriving in the 1820s and 1830s.

People came from New England, Virginia, South Carolina, and even from the Bahamas. Many were looking for adventure or opportunity. In 1828, Key West was officially incorporated as a city.

Among these early settlers were people who became known as Conchs (pronounced “konks”), named after the large shellfish that is still a popular food in the Keys.

The term originally referred to English settlers from the Bahamas, especially the descendants of Cockney fishermen. Over time, “Conch” became a proud label for anyone born and raised in Key West.

The Conchs built industries that would support the island for decades. The most important at first was wrecking, but soon another business emerged: sponging.

The waters around the Keys were rich with natural sponges, and Conchs developed clever ways to harvest them. Greek immigrants also joined the trade, diving deep with weighted shoes to collect sponges. This created fierce competition and even fights between Conchs and Greeks.

By the 1940s, however, sponge blight nearly destroyed the industry.

Prosperity Breeds the Wealthiest City in America

• 

  First cigar factory opens in 1831.

• After Cuba’s 1868 uprising, thousands of Cuban cigar makers flee to Key West.

• By the 1890s, over 100 million cigars annually produced.

The 1830s through the mid-1800s are the core years when Key West is widely described as the wealthiest U.S. city per capita (meaning: the most money per person, not the biggest total economy).

Contemporary and scholarly summaries consistently place the peak in the 1830s, with prosperity continuing through the 1840s–1850s. 

The money came from “wrecking”—a legal salvage industry born from the Keys’ dangerous coral reef.

Ships struck the reef frequently; fast local boats raced out to rescue crews and salvage cargo, which was then appraised and auctioned in Key West.

The salvors (wreckers) took a large court-awarded share, and the town boomed on fees, storage, repairs, and trade that spun up around it. In heavy years, over $1,000,000 in vessels and cargo were wrecked on the reef (19th-century dollars).

In 1846 alone, $1.6 million in goods were recovered—an enormous sum at the time. 

To support all that activity, the U.S. created the Superior Court at Key West in 1828 with admiralty jurisdiction to license wreckers and run the salvage process.

That centralized nearly all Florida reef salvage through Key West, concentrating wealth here. (Judge William Marvin later refined the salvage law, becoming a key figure.) 

At the boom’s height, auctions, chandlers (ship-supply shops), ropewalks, boatyards, warehouses, and lookout towers filled the waterfront. One popular (and telling) period estimate: a ship went aground in the Keys about once a week. 

Safety tech: After the big 1846 hurricane, the federal government accelerated lighthouses and reef beacons (Carysfort, Sand Key, etc.).

Safer navigation meant fewer wrecks, so the easy money slowed by the early 1850s. A contemporary newspaper noted the wrecking “falling off” once those lights were up.

Economic Shocks to Key West: Major storms (especially 1846) battered the town, wharves, and stores; later, the Great Fire of 1886 hurt the commercial base, too. 

Economy Booms Again With Cigars: Thousands of Cuban torcedores (rollers) settled in Key West after 1868, and by the 1890s the island produced ~100 million cigars a year—a second prosperity engine that kept money flowing, even as some factories later migrated to Tampa.

Revolution and Refugees

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  José Martí rallies Cuban exiles in Key West during 1890s.

• Key West becomes a staging ground for the Spanish-American War in 1898.

Cuban immigrants didn’t just bring cigars—they also brought revolutionary ideas. The writer and activist José Martí lived in Key West in the 1890s. From the island, he helped organize the Cuban War of Independence against Spain. Martí’s fiery speeches inspired the Cuban community.

When the Spanish-American War broke out in 1898, Key West became a staging ground for U.S. naval operations. The island’s location—just 90 miles from Cuba—made it a crucial base.