Key West: A Brief History

Key West's story starts long before Duval Street had a single bar on it. This small island at the end of the Florida Keys has been named by an empire, bought for $2,000, burned down, gone bankrupt, and reinvented itself more than once.

Here at Marreros Guest Mansion, we've had a front row seat to a good stretch of that history. Our home on Fleming Street has stood since around 1890, which means it has outlasted the cigar boom, the Depression, a hurricane or two, and whatever the 1980s were doing to Duval Street.

When was Key West founded?

Key West was founded in 1822, the year businessman John W. Simonton bought the island (January 19) and the U.S. Navy planted an American flag on it (March 25). Before that, it was a Spanish land grant that nobody had gotten around to settling: Spain had granted the island to an army officer named Juan Pablo Salas in 1815, and it was Simonton's purchase that set the first permanent settlement in motion.

Who founded Key West?

John W. Simonton, a businessman who bought the island from its Spanish owner for $2,000 in January 1822, is the person most often credited with founding Key West, along with the partners who shared in the purchase. Those partners were John Whitehead, John W. C. Fleeming and Pardon C. Greene, the four owners who had the town surveyed, mapped and settled, while Simonton spent his summers in Washington lobbying for a naval station, a federal court and a port of entry. Native peoples had lived in the Keys for thousands of years before any of these gentlemen turned up, and the Spanish were already calling the island Cayo Hueso ("Bone Island") long before English speakers mangled it into Key West.

When was Key West established?

Key West was legally established as a municipality in 1828, when the Florida territorial government incorporated it, and it received a full city charter in 1832. The paperwork was a little messy: an act incorporating the "City of Key West" passed in January 1828, was repealed that November and replaced with one incorporating the Town of Key West, which gave way to the chartered city, with a mayor and six councilmen, in 1832. The same year the island was incorporated, Congress set up a federal court there so shipwreck salvage cases could be heard on the island instead of in St. Augustine, and the wrecking business took off.

How old is Key West?

Key West is more than 200 years old if you count from 1822, when the island was bought and claimed for the United States. Count from its 1828 incorporation and it is six years younger. European ships were passing these islands more than 500 years ago; Ponce de León sailed by in 1513. Count the Indigenous peoples who were here first and you will need a bigger birthday cake.

What is the history of Key West?

Key West's history in one breath: a Spanish-named "Bone Island" that became a U.S. Navy outpost in 1822, then a shipwreck-salvage boomtown, a cigar-making powerhouse, a Depression-era bankrupt, a presidential getaway and, in 1982, a very small pretend country. 

The money came first from shipwrecks: after Congress set up a salvage court on the island, Key West grew into the wealthiest city per capita in the young United States. Cigars came next. The first cigar factory opened in 1831, and the industry took off after 1868, when Cuba's rebellion sent Cuban cigar makers across the Florida Straits and Key West became the primary producer of clear Havana cigars. 

Then the 20th century got rough: the city declared bankruptcy in 1934, and federal relief officials set about reinventing it as a vacation destination. 

By 1946 the reinvention had a presidential stamp of approval, when Harry Truman arrived for the first of eleven working vacations at the Little White House. And in 1982, when a Border Patrol roadblock strangled tourism, Key West responded by declaring itself an independent (tongue-in-cheek) nation, the Conch Republic, and surrendering almost immediately.

Key West history timeline: what happened when?

• 1513: Ponce de León sails past the Florida Keys and records them as Los Mártires ("The Martyrs").

• January 19, 1822: John W. Simonton buys the island from Juan Pablo Salas for $2,000.

• March 25, 1822: Lt. Matthew C. Perry plants the U.S. flag on the island.

• 1823: Commodore David Porter arrives to set up a naval depot and end piracy.

• 1828: Key West is incorporated, and a federal court opens for shipwreck salvage cases.

• 1831: William H. Wall opens the island's first cigar factory.

• 1832: Key West receives its city charter.

• 1845: The Army begins building Fort Taylor.

• 1868 to 1869: Cuba's rebellion begins and Cuban cigar makers arrive in force; Vicente Martínez Ybor opens a Key West factory in 1869.

• 1890: Cigar maker Francisco Marrero builds the mansion that is now Marrero's Guest Mansion.

• 1912: Henry Flagler's Overseas Railroad connects Key West to the mainland by land.

• 1934: Key West declares bankruptcy.

• 1935: The Labor Day Hurricane severely damages the railroad.

• 1946: President Truman makes the first of eleven visits to the Little White House (November).

• April 23, 1982: Key West declares independence as the Conch Republic.

Onward from the 1990s, Key West developed into the city it is today! This quiet town became notorious for being "the party city", with Duval Street becoming legendary for its rows of bars leading all the way down to the waterfront. The population is a mix of full time locals, "snowbirds" (people who stay for the winters), and bustling tourists. Wander the old streets, admire the architecture that survived hurricanes and economic crises, and notice the historical landmarks.

Want to learn more? Read more online - see this article by the Historical Preservation Society of the Upper Keys about Key West's colorful history. If you're already in town, shop small at Books & Books or the Key West Island Bookstore for local authors & books on the island's history. If you're feeling brave, you may even want to pick up what Key West has become notorious for: Ghost Stories.

Living History: Experience Key West

Marrero's Guest Mansion has stood its ground from the early ages of Key West. While its ownership began with the scandalous story of the Marreros, it's been passed down through many hands over the years, eventually joining the {verdigreen} hotels family. As of 2021, Marrero's underwent much needed renovations, lovingly restored to a Hollywood Regency inspired interior. Follow the footsteps of the past as you enter the premises, knowing you're a part of history in the making.

Which brings us home. Francisco Marrero was a cigar maker with family roots in Cuba, working in the years when Key West was the primary producer of clear Havana cigars, and in 1890 he built this mansion for Enriquetta. The cigar boom eventually moved on to Tampa, and the Marreros' happy years in the house were short-lived, but the house is still standing and, if you believe the locals, so is Enriquetta. 

The full story, scandal and ghost included, is on our history page.

We hope you enjoyed our brief dive into the past. We look forward to hosting you when you stay with us.

Thanks for reading,

The Marrero's Team

Traveling elsewhere in Florida? Visit our sister property in Treasure Island FL.

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