The History Of Key West

When visiting Key West, travelers often say it feels like they are “stepping back in time.” Not to be confused with “island time,” the term for the laid-back, slower pace of life that happens on the island. the former represents the rich history of Key West and the fact that it was all but isolated until the early 1900s.

While the island has since been developed and is primarily a tourist town today, many of the local attractions are sites of historical significance.

A Brief Overview Of The Island’s Early History

Long before European explorers and later settlers visited the island, it was inhabited by the native Calusa people. Famous Spanish explorer, Juan Ponce de Leon was one of the first to come across the island in his search for the Fountain of Youth. While he didn’t find the fountain, he did not find a shortage of bones from prior inhabitants. In fact, the original Spanish name for the island is Cayo Hueso, meaning Bone Cay, because the Calusa people used the island as a communal graveyard.

Settlement of the island went back and forth between Spain and Great Britain several times before it was finally sold to John W. Simonton in 1821 on the recommendation of his friend, John Whitehead who saw the potential of the island’s deep harbor. Along with Simonton and Whitehead, additional undeveloped plots were sold to Pardon Greene and John Fleming. The four became the founding fathers of what we know as modern day Key West. When you visit the island you’ll see these famous names on street signs and buildings, but what about the infamous Duval Street? It was named after Florida’s first territorial governor, William Pope Duval.

Fast Forward Through War And Immigration

Key West was divided during the American Civil War. While Florida had seceded to join the Confederacy, Key West remained a Union territory due to the US Naval Base Fort Zachary Taylor being located on the island. A previously thriving salt manufacturing industry on the island was shut down when Confederate sympathizers were caught smuggling salt into the south. A hurricane in 1876 changed the topography which shifted salt deposits from the island to the mainland and shutting down the industry completely.

Then came the Ten Years’ War where Cuba tried unsuccessfully to gain its independence. During the strife, many Cubans made the 90 mile boat ride to Key West seeking refuge. Their influence is still strongly seen today in the culture, food and music of the island.

From there, relations between the US and Cuba went downhill quickly, culminating in the Spanish-American War, the Cuban Mission Crisis, and eventually the Cuban Revolution, which closed the door on commerce and travel until recently.

Modern Key West

Key West was only accessible by boat until 1912 when the Overseas Railway was built connecting it to the mainland. The railway was later destroyed in a 1935 hurricane, and reconstructed as the Overseas Highway, for automobiles, in 1938.

But in the more than 100 years that Key West was disconnected from the mainland, it was developing nonetheless. The diverse settlers that built up the island brought with them their own cultures – Spanish, Cuban, European – and each influence can still be seen in the unique architecture and culture of the island.

Today, visitors can take historic walking and trolley tours to see the island’s most prominent attractions, like the Hemmingway Home and Former President Harry Truman’s Little White House, where several U.S. Presidents have vacationed in the winter months.

Start Your Historic Key West Adventure With Salt Island Seaplanes

When you’re ready to immerse yourself in the rich history of Key West, start your adventure with an exhilarating seaplane ride with Salt Island Seaplanes. Departing from Naples and Fort Myers, a quick flight over the pristine waters of the Florida Bay will have you touching down in Key West in no time.

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Naples Office & Terminal
574 Terminal Drive
Naples, FL 34104

Fort Myers Terminal
5200 Captain Channing Page Drive
Fort Myers, FL 33907

(239) 263-SALT (7258)


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