Key West History & Images

  Please Scroll Down to view Images of Old Key West

Key West, or Cayo Hueso (Bone Key) was discovered by Ponce de Leon and claimed by Spain in 1513.

In 1815 Don Juan de Estrada granted Key West to Juan Pablo Salas for his meritorious service.

John W. Simonton, from Alabama, bought the island from Salas for $2,000 in 1821. Lt. M.C. Perry, USN took possession of the island in 1822 and claimed it for the United States as part of territory ceded from Spain.

In 1823 Key West was claimed a port of entry to the United States, the first customs house was opened and the first Naval Depot was established. The Marines came in 1824 and the Army came in 1831.

Throughout the history of the Florida Keys, pirates such as Blackbeard & Jean LaFitte became a problem.  Commodore David Porter was dispatched to end it in 1822.  At that point in time, wrecking and salvage became a principal occupation of the islanders.

In 1828, Congress established the Superior Court of the Southern Judicial District of Florida at Key West, which allows salvage court to be held in Key West, as previously it had to be held in St. Augustine. This allowed for a growing salvage industry and increase in population of the island.

In 1829 Key West got its first post office and in 1831 William H. Hall established the first American cigar factory in Key West.

The military constructed Fort Taylor in 1845 and in 1846 began Fort Jefferson in the Dry Tortugas, 60 miles off Key West.

In 1832, Key West became a full-fledged city.

In 1836 the East and West Martello Towers were constructed. Interestingly enough during the Civil War the Southernmost City in the United States remained in the hands of the Union.

The 1846 hurricane destroyed much of Key West, which at that time extended no further east than White Street. The rest of the island was considered “country” and salt ponds.

In the 1850’s, a series of lighthouses were erected along the reef from a point near Key Largo to Key West. The marking of the dangerous reef allowed for safe navigation of the waters in the Keys and caused the salvage industry to decline.

Sponging, fishing and farming of pineapples, Key limes, tomatoes and melons were a mainstay on the Keys, while Key West enjoyed it’s “Metropolitan” flavor, military support, deep water port and industrial life of the cigar makers.

Between 1863 and 1886, the San Carlos Institute was established and Cubans began migrating to the United States through Key West, which continued to be a wealthy and prosperous city.

Then, in 1886 half of the city was again destroyed, this time by fire.

In 1904, Henry Flagler began his Overseas Railroad to Key West.  It was completed in 1912. Key West prospered as trainloads of wealthy from the north would come to stay on Key West, at the exclusive Casa Marina resort Flagler had built. The current Customs House and Federal Building were completed.

The Great Depression in the 1930’s put Key West into impoverishment. Rehabilitation was begun by the Florida Emergency Relief Administration. Economic experts were imported to evaluate the future of Key West. Their answer was “tourism”.

In 1935, a Labor Day hurricane wiped out the Florida East Coast Railway and killed 500 people in Upper Matacombe, north of Key West.

Henry Flagler’s dream came to an end. In 1937 work began to construct a highway over the railway bed.  It opened to traffic in 1938. 1942 saw the completion of the Overseas Highway.

In 1939 the government established a submarine base in Key West and in 1940 the first Naval Air Station opened.

In the 1940’s President Harry S. Truman enjoyed his stays in Key West where he had established his “Little White House.”

1940 and 1950 the population doubled in Key West. Monroe County Beach was opened and in 1952 the passenger-auto ferry from Havana to Key West was established.

<< Mike & Diane's Brief History in Key West >>

In 1957, Mike's Navy Family moves to Key West.

In 1961, Mike's Dad retires from the Navy and his family moves back to Pennsylvania.

In 1961, Diane's Navy Family moves to Key West.

In January of 1962, Mike moves back to Key West and works at the Gulfstream Market on White Street.

In August of 1962, Mike leaves Key West and enrolls at St. Petersburg Junior College in Florida.

In 1964, Diane's Dad retires from the Navy and moves to Illinois.

In 1980, Diane returns to Key West to begin teaching 5th Grade at Sugarloaf Elementary School.  Diane's 1st teaching position in her teaching career. 

In 1961 relations with Cuba were suspended and Key West suffered yet another economic blow. The revolution in Cuba created an influx of  Cubans to Key West in their desire to escape Communism.

Key West was a sleepy town through the 70’s. The military came and went and came back. The great shrimping industry began to decline and sought other coastal areas to base their operations. Writers, painters and a number of artists were imported to stimulate the tourist trade again. Many famous authors and writers did make Key West home or at least a “second home”. Ernest Hemingway. Robert Frost, Elizabeth Bishop, Ralph Ellison, Philip Burton, James Herlihy, Phil Caputo and Tennessee Williams, were among the more well known.

In November 1971, Jimmy Buffett arrives in Key West and looses his Jigger of Salt somewhere on Duval Street. 

The Good News, Jimmy put Key West on the Destination Map!

The Bad News, Jimmy put Key West on the Destination Map!

Thanks Jimmy, we love you no matter what ... you forever changed Key West with your music!

In 1982, the Conch Republic was established. This creative republic drew attention to the serious economic problems the Keys and Key West were once again experiencing. In 1982, the Federal Customs Agents set up a barricade at the top of the Florida Keys, in search of aliens, drug dealers and drugs being brought in from waters around the Keys. The agents identified themselves as a “Border Patrol” and held up traffic for hours searching vehicles and seeking identification of passengers. The mayor of Key West and various political leaders protested to the U.S. Government and seceded from the United States in order to draw attention to the economic plight created by the situation.

Thus the Conch Republic was born! A Prime Minister, Ministers of Justice, Education, Tourism and an Admiral of the Fleet were appointed and to this day April 23 is celebrated as Conch Republic Day. Key West was the mouse that roared.

The 1990s have seen much growth and development in the Keys and Key West. The once sleepy Duval Street is like a big city “downtown” with bars, tee shirt shops and tourist shops intermingled with artists galleries, fine restaurants and exclusive designer shops. The hustle and bustle of the “good times” is back. Key West International Airport averages over 26,000 passengers a month. Approximately 28,000 call Key West home according to the 1990 U.S. Census and 6,500 more are “snowbirds” or part-time winter residents. There are approximately 80,000 residents who live elsewhere on the islands of Monroe County and 45,000 who visit seasonally.

September 1, 2023 Jimmy Buffett passed away peacefully surrounded by family, friends and dogs.  His music will live on across Time & Eternity,  RIP