Florida Keys – A Magnet for Famous Characters

Over the years, many people helped create the Florida Keys we know today. Some lived there, others only visited. Today, Mallory Square Sculpture Garden displays busts of people who impacted Key West. From Bogart to Hemingway to President Harry Truman, the Florida Keys has always been a magnet for famous characters.

Humphrey Bogart

Humphrey Bogart spent a brief time in the Keys while filming Key Largo. But the islands created a history around the legendary actor.

A restaurant in Islamorada boasts ties to the Bogart story. Housed in a building dating to the 1930s, Ziggie and Mad Dog’s began when Ziggie Stocki, a notorious gambler and supposed friend of Al Capone, bought it in 1948 and opened Ziggie’s Conch. John Huston is said to have devised the plot of Key Largo while gambling with Ziggie. There’s no proof, but the movie does include a gangster character named Ziggie. Today, the upscale restaurant specializes in steaks and fresh seafood served with orchid-garnished cocktails or fine wine.

The Bogart movie African Queen is based in Key Largo at the Holiday Inn Marina, which is across the Overseas Highway from the Caribbean Club, where the exterior shots of the hotel were filmed. Unfortunately, the hotel burned down and only the bar remains.

African Queen Photo: Kathleen Walls

Cruising on the African Queen

Built in England in 1912 as a work boat for the British East African Railway, the African Queen is now available for cruises. On my cruise, Captain Duncan shared the history and backstory of the famous boat and its namesake movie.

When John Houston found the boat in 1951, he hired it for the movie and changed its name to African Queen to fit the script. After the movie, the boat was returned to work in the Belgian Congo for six more years.

After it was retired, the African Queen went in and out of storage, primarily off the radar, until it ended up in a cow pasture in Ocala, Florida. Jimmy Hendrix, who owned the Holiday Inn in Key Largo then, found it. He restored it and began tours in Key West and around the world.

As his health deteriorated, so did the boat. Lance and Suzanne Holmquist fell in love with it and now lease it long term and take outstanding care of it.

Captain Duncan took us out into the Atlantic, let us steer it, and reenacted some scenes from the movie. Put this on your bucket list when you go to the Keys.

Sails to Rails Museum Photo: Kathleen Walls

Henry Flagler

In the late 1800s, Key West’s frequent shipwrecks, salvaged by locals known as “wreckers,” made it the richest city per capita in the United States. Key West Shipwreck Treasure Museum in Mallory Square tells the story of the wreckers.

However, you could only get to Key West by ship until 1912, when Henry Flagler accomplished the supposedly impossible by bringing the Florida East Coast Railway from St. Augustine to Key West. Several places tell the story. Exhibits at Sails and Rails in Key West tell the railway story, plus the earlier ship’s stories.

The Keys History & Discovery Center on Islamorada exhibits tell the entire history of the Florida Keys. I highly recommend the documentary about building Flagler’s railroad.

Crane Point Museum and Nature Center in Marathon, Florida, is a wonderful blend of history and nature. Besides the historic Crane Mansion and the wild bird sanctuary, the museum houses a preserved train car that was once part of Henry Flagler’s Overseas Railroad. The train tour provides the best way to see the entire attraction.

The Custom House Museum at Mallory Square also feature exhibits about both Henry Flagler and Ernest Hemingway.

Six-Toed Cats’ Condo at the Hemingway House Photo: Kathleen Walls

Ernest Hemingway

When you think of Key West’s creative legacy, Ernest Hemingway is the first name that comes to mind. The Nobel Prize-winning author lived in Key West in the 1930s with his second wife, Pauline Pfeiffer, whose uncle, Gustavus (Gus) Pfeiffer, gifted them their home. Hemingway wrote some of his most famous works there, including To Have and Have Not, his only novel set in the United States. Today, the Hemingway home serves as a museum.

A bevy of six-toed cats is a favorite of visitors to the Hemingway House…myself included. They are friendly and will let you pet them. The cats began with Snow White, a white six-toed cat given to Hemingway by Captain Dexter when his six-toed cat, Snowball, had kittens. Hemingway began adopting many other cats and owned 50 at one time. There is a marker entitled “Captain Dexter and Snowball: The First Six-Toed Cat”

One of Hemingway’s favorite haunts, Sloppy Joe’s Bar, hosts an annual Hemingway Days Festival and Look-Alike Contest. On my Old Town Trolley tour, the driver shared the story of how Hemingway tore out a urinal at Sloppy Joe’s Bar, took it home, and made a drinking dish for his cats.

Sloppy Joes was initially located in what is now The Green Parrot. When the landlord tried to raise his rent by one dollar, the bar owner, Joe Russell, told his patrons to grab their barstools and drinks and move across the street and up the block to the present location on Duval St. Both bars are worth a visit.

The Little White House Photo: Shutterstock

Harry Truman

Harry Truman faced some of the most complex issues any president has faced. Should he drop the first atomic bomb, which he had never known was in the works until after Roosevelt’s death, and end the war? Should he desegregate the armed forces even though it was controversial? Could he deal with rebuilding Europe and creating a Jewish state after WWII? He answered yes to all these challenges and more. It was no wonder he had health problems.

When he came to Key West in search of a place to recuperate and relax, he stayed in naval officers’ housing constructed in 1890. He loved Key West and had the former naval quarters fitted out for his family. He spent 175 days of his presidency living in what is now known as The Little White House.

The Little White House is Florida’s only presidential museum. Our guide, Steve, did an excellent job showing us Harry-the-man, who wasn’t used to being waited on and liked to barbecue hot dogs and hamburgers on a brick grill in the yard himself. Truman loved playing poker and drinking bourbon and had a Key West mahogany poker table. Since gambling was illegal, there was a special cover-up top made that turned it into an innocent large round table. He also showed us President Truman, who worked tirelessly to deal with the Cold War, the creation of NATO, the Central Intelligence Agency, and the G.I. Bill to help returning military. This is one place you must visit.

More Famous Characters from the Florida Keys

There are many other vital people when you think of the Keys. Mel Fisher’s museum highlights the famed treasure hunter. And, of course, Margaritaville represents Jimmy Buffett.

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