The Craziest Things About Key West

There are more than hundreds of crazy things about Key West so these are my favorite crazy things about Key West, that little island at the end of the Florida Keys that is as close to Havana as Miami.

Key West may seem like a different planet even to Floridians, but that is what makes it a wonderful tourist destination if you come to the Sunshine State.

Here are some of my favorite Key West things:

THE CONCH REPUBLIC is more than a flag in Key West.  It reflects the personality of the locals probably developed by the island’s populace being isolated from mainland Florida and their independence from outside influences.

When Florida seceded from the Union in 1861, Key West seceded from Florida and remained in Union hands.  Well, except for one lady who kept flying a Confederate flag from her waterfront house.  Locals removed the flag, but she made three others.  Eventually, they let her keep it up


We cats own this Hemingway place and don’t forget it!

ERNEST HEMINGWAY’S CATS are the most popular attraction at the famous author’s Key West retreat.  The author may have been blown away, but his six-toed cat’s ancestors are still around and people spend as much time looking for felines as looking at the rooms and the island’s first swimming pool.

ERNEST HEMINGWAYS BY THE DOZEN.  Key West loves festivals and parades as long as there is a lot of drinking and fun.  Actually, that happens every night anyway.  The city’s Ernest Hemingway look-alike festival is a photo treat.

Running of the bulls? No running of the Hemingways!

THE KEY WEST CEMETERY is proof that the city is full of creative and often batty people. A casual walk in the cemetery will show the diversity of the city’s history.  Remember the issue of salt-water intrusion.

Even in death you will read my words and learn.
An “UNDERstatement”

SLOPPY JOES  is a Hemingway institution and visited by more people than Key West’s museums, but take a visit to the place next door and you will find information that Hemingway hung out here.  Sloppy Joes had a big brawl a few years ago – the cause was that someone farted.

LIKE VENICE, KEY WEST IS DROWNING. As the world’s waters slowly rise, Key West suffers from serious flooding during winter storms and hurricanes.  Eventually, I think, Key West may be known as “The Netherlands of America.”

Shoukd Key West rent some gondolas from Italy?

CHICKENS OUTNUMBER SEA GULLS.  I live in Tampa and our Latin Quarter Ybor City has a lot of chickens and roosters running about, but as an island, I am amazed at how the Key West chickens tell the seagulls to stay on the beach.

Now let’s play Where Is Waldo again. Note that birds avoid streets.

THE SOUTHERNMOST POINT is one of the most photographed spots in Florida, but it is amusing in many ways.  Florida extends southward from Key West to the island with Fort Jefferson, another fifty miles.  One could even debate whether Key West, an island, is part of the Continental USA.

Did you know that a 64-year old grandmother swam from Cuba to Key West?

GEORGE IGNACIO MIRA, with baseball star Boog Powell, was probably Key West’s greatest athlete and star quarterback at the University of Miami.  When I was sports editor of the Miami Hurricane I “interviewed” him, but I could hardly understand him for his “Key West Conch” accent was something a New Englander could not quickly grasp.

Miami’s offensive line came mainly from Pennsylvania and I wondered how they ever got a play right. One guy said, “It was like having Desi Arnez as our QB.” Mira or his teammates must have adjusted for Mira played 8 seasons in the NFL, 1 in CFL, and 1 in WFL where he was MVP of that league’s championship game. Mira later opened the George Mira Pizza Huddle in Key West.

Tune in for my ebooks and PODs that will be coming out in a few months.

About floridatraveler

Historian and travel writer M. C. Bob Leonard makes the Sunshine State his home base. Besides serving as content editor for several textbook publishers and as an Emeritus college professor, he moderates the FHIC at
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