Here's a super summary of Key West's distinguished and crazy history: Ponce de Leon was the first European, setting foot on the Key West swamps in 1521.
Then not much happened for 300 years until businessman John Simonton purchased Key West in a Havana bar in 1822 for $2000. Greene, Whitehead and Fleeming laid out the island plan in 1829 (and stole for themselves the names of the best streets).
Life in Key West was then dominated by - in turn - shipwrecking, sponging and cigar making, all of which left their particular marks and scars on the city. Key West was in glorious isolation until 1912 when the rail road arrived thanks to 42 bridges and the determined and expensive efforts of billionaire Henry Flagler, then it was blown away in 1935 by the most intense hurricane ever to hit the USA, which killed the railroad link and 408 people.
Then there was an arty phase with Hemingway and Williams and others. Once America's richest city per head, it was for 30 years a poor and run down place until someone came up with a bright idea of tourism.
A restoration movement started in 1960 thanks to tight knit community spirit. The first cruise ship arrived in 1969 and started an unstoppable trend that now results in over 1 million tourists per year and all the stresses that produces on this tiny tropical place.
A little bit more....
Key West is island #823 - and is tiny, geographically speaking
Key West is an island of 7.4 square miles in Florida, 129 miles from Miami and 106 miles from Cuba.