Relaxing days in the Conch Republic: Key West, Florida

Tropical garden at the Audubon House

In our first 24 hours in Key West, we visited a place called The Audubon House that Audubon never lived in or even visited, went to Mallory Square for a fabled sunset celebration known for its street performers, including jugglers, clowns, psychics, artists, and musicians, that was, in reality, just a disappointingly small gathering of tourists watching the sun set, and visited Sloppy Joe’s, a bar famous for being a haunt of late author Ernest Hemingway that, in fact, Hemingway never set foot in. Here are the real stories behind this lore:

Audubon House: The connection of John James Audubon to the Audubon House is that the artist once painted a picture of a White Crowned Pigeon in a Cordia tree that was on the property where the home would eventually be built. A merchant who bought the house in the 1950s was an admirer of Audubon and put his collections of Audubon paintings in the house, including the White Crowned Pigeon. So, no actual connections to John James Audubon.

Mallory Square sunset: The famous sunset celebration at Mallory Square apparently went on daily for years – our friends in Orlando, Scott and Carolyn McClendon attest to this – and we were told about it by a tour guide on our first morning in town as though it still exists. Although it’s true that the sun does still set in that same place, it now does so without all the hoopla.

Sloppy Joe’s: Sloppy Joe’s does exist on Duval Street in Key West, but in Hemingway’s day was housed in a completely different building that is now called Captain Tony’s. Back in Hemingway’s day, “Sloppy Joe” Russell ran a bar in the back of a morgue in the building that is now Captain Tony’s. Some believe that this was the inspiration for a bar called “Freddy’s” in Hemingway’s novel To Have and Have Not.

Did these deceptions dampen our enthusiasm for Key West? Not in the least! Well, we were maybe a teensy bit let down to miss the jugglers, clowns, and magicians on Mallory Square at sunset. So, we did what any disappointed tourists to Key West would do: we drowned our sorrows in Key Lime Pie.

Who needs jugglers and clowns when you can get Kermit’s Frozen Key Lime Pie on a stick, covered in Belgian dark chocolate?

It could be argued that the lore and the stories, true and untrue, are part of the romance that makes Key West so special. After spending a short three days in the city, we felt that it’s more about being there than it is about doing things. We stayed at the tidy, mid-century Harborside Motel which was, of course, near the harbor and a bike ride of about nine minutes to anywhere on the island. One of our great pleasures of being on the island was the bike rides around town, through the neighborhoods and the cemetery, out to the botanical garden, and along the waterfront. Biking, by the way, is a great way to get around Key West and avoid parking challenges.

Key West is known for being the site of the Southernmost point of the U.S. – it may or may not be on this spot
At the famous “Mile Zero” marker for U.S. 1 which extends from Key West all the way to Maine

From Pirates, Cigars, Chickens, and Submarines to Margaritaville

So, here’s a brief (very brief) history of Key West. Discovered by Ponce de Leon in 1513 and claimed by Spain, it was sold to a guy from Alabama in 1821 and shortly thereafter, formally became part of the United States, after which, a port was developed that, of course, attracted pirates, including Blackbeard and Jean Lafitte. Local commerce in those days was claiming wreckage and salvaging treasure from the many ships that ran ashore. Captain John Huling Geiger, who built Audubon House, made his fortune this way. The cigar industry was also a local concern, in addition to the sport of cockfighting. The descendants of the fowl used for cockfighting roam the streets of Key West to this day.

These beautiful chickens were everywhere in Key West and even up in Tampa at Ybor City

Key West grew and, in spite of hurricanes and fires, was a prosperous city by the time Henry Flagler built an overseas railroad to the island that was completed in 1912. The remains of the long-abandoned railroad can still be seen on the drive from Florida City across the keys to Key West. Famous folks, including Earnest Hemingway and John dos Passos lived on Key West in these years.

In the 1930s, the Depression and a 1935 hurricane ended the railroad and with it, this period of prosperity, until, in 1940, a submarine base and Naval Air Station were opened and work on a highway began. Later, President Harry Truman would deploy an officer’s house at the Naval Air Station and turn it into the Truman Little White House. By the 1970s, the military presence had waned and Key West was, once again, in a slump. Enter Jimmy Buffet, who arrived in Key West in 1971, along with his pal, Jerry Jeff Walker. Buffet’s marriage to his high school sweetheart had just ended and his career was in a slump, so he headed to Key West and ended up playing in local bars for drinks, eventually writing Margaritaville in 1977 and the rest, as they say, is history. Jimmy Buffett is credited locally with ushering in the tourist boom that Key West enjoys to this day.

So, to recap, 1. pirates, wreckage, cigars, cockfighting, hurricanes/fires; 2. railroad, Hemingway, depression, and a big hurricane; 3. submarines, Truman, everybody left; 4. Jimmy Buffet, tourists came and never left. That’s all you need to know.

President Harry Truman’s car – the Truman Little White House is definitely worth visiting
We loved seeing the beautiful Bougainvillea everywhere!
On the Key Lime Bike tour – it’s a great way to pass a morning and get to know the city and it ends with a complimentary slice of local Key Lime Pie!
A little gallows humor in the Key West Cemetery, which we rode through on our bikes daily
And someone at the Botanical Garden has a sense of humor….
Pelicans were shameless beggars, trying for the bait at the places where tourists hand feed Tarpon from the dock
Is Flipper trying to tell us something? On a boat ride through the Mangrove islands in Everglades National Park

Meanwhile, on to Sanibel and Tampa/St. Pete

We were sad to leave Key West, but we were headed north to additional fun destinations: Sanibel is a beautiful, pristine island with a wonderful wildlife refuge and lovely beaches. St. Pete has become quite the museum city, with a destination-worthy Salvadore Dali museum, a center devoted to Dale Chihuly’s fabulous glass art, and a new four-story, museum devoted to the early twentieth century Arts and Crafts museum with furnishings and art pieces from that period. We enjoyed going to historic Ybor City, famous for its cigar industry, and riding bike trails in Pinellas County out to Honeymoon Beach State Park with my cousin, Geri.

An Ibis and an Egret walked into a (sand)bar…(at the Sanibel Wildlife Refuge)
Cormorant enjoying still water
No trip to Tampa is complete without a visit to the beautiful and historic Columbia Restaurant – be sure and try their Cuban sandwich
At Honeymoon Beach State Park with my cousin, Geri
Disco Manatee on Sanibel Island
Sanibel Lighthouse, which must have been an oil derrick in its former life
Beautiful Key West sunset, viewed from Mallory Square

10 thoughts on “Relaxing days in the Conch Republic: Key West, Florida

  1. Beautiful images. The mythbusting day must have been a hoot. And the others sound like adventures on a stick. Great to see y’all. Thanks for the tale.


  2. Hi, Sallie,

    Oh, this is so well-written and entertaining. Thank you for sending!

    I am in the throes of getting the house emptied out. The closing is on Thursday. And then on Friday, I close on a sweet little condo I found in Tarpon Springs!

    Then I will close the door and drive off to Wyoming probably on Sunday. Whew.


    Sent from Mail for Windows


    1. Thanks, Geri – we had such a great time seeing you and spending time in Clearwater! Good luck with the move, and I’ll see you soon in Saratoga or Thermopolis!


  3. I meant to tell John yesterday how much I enjoyed your Key West commentary.

    *Bill Williams* *7515 Jefferson Hwy #308*

    *Baton Rouge, LA 70806225-938-1174*

    * *

    Liked by 1 person

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