“Close To Perfect, Far From Normal” (Key West Chamber of Commerce)
What makes Key West, Florida so appealing to tourists? On the surface, it appears as a typically serene tropical island blessed by swaying palm trees, endless shopping opportunities and white sand beaches along a sun kissed shoreline. The first time tourist might hop on the popular tourist conch train for a 90 minute guided sightseeing tour of the main sights in Old Town, munch on local seafood in an airy terrace overlooking picturesque Mallory Square and pop into a local souvenir shop or two along crowded Duval Street for shopping to their heart’s content.
Yet if you stay awhile in Key West, you might look beyond such conventional tourist impressions to realize that a spirit of fantasy weirdness provides unique attractions to this sleepy town. Three personal memories of Key West oddness seem to contradict the foregoing, casual tourist” theory of this slow moving town: (1) spotting an aging OJ Simpson in dark sunglasses sauntering inconspicuously along Duval Street with his young girlfriend,(2) gazing at the webcam posted near Sloppy Joe’s Bar regularly portraying hedonistic tourist madness or (3) dodging the overgrowth of feral cats along the famed Hemingway House tour.
My knack of finding the bizarre in Key West continued on our self guided walking tour of Old Town at this last stop of our recent Caribbean cruise. Adventuring off the beaten track to avoid tourist hustle on a Monday morning, ten historic/cultural oddities caught my photographic attention as briefly described in the paragraphs below.
1. Follow the crazy roosters around town
Disembarking from the cruise, we were strangely greeted by a flock of noisily crowing roosters surrounding us as we made our way to town. I wonder what welcoming message they were trying to convey to me at the time?
2. Get lost in cemetery tombstone madness
In the “dead” center of town, above ground gravesites covered by weirdly customized tombstones filled the Key West cemetery grounds. Some burial chambers inscribed unusual epitaphs – “I Told You I Was Sick” and “ At Least I Know Where He Is Sleeping Tonight.”
3. Seduce your artistic mind in Haunted House Heaven
Willie Smith, reclusive grandson of a prominent Key West Sea Captain, John Geiger lived for over twenty years in his family’s spooky 19th century mansion with shuttered windows and no electricity or running water. Who could imagine that an exquisite collection of John James Audubon birdlife portraits would thus be later displayed on this later museum site amidst these dark and dreary hallways.
Advertised historically as a brothel in early Key West times, this quirky outdoor cafe amusingly advertised showers for $2.00 and watching those who bathe for $1.00. As we indulged in our omelets, the ever present roosters surrounded us again.
5. Celebrate holiday festivities in odd Key West fashion.
The Yuletide Spirit can be demonstrated here in unusual ways before Christmas with utility light poles attached to giant candy canes and mini Santa clad gnomes placed on top of patio furniture.
6. Hang out near bars that offer weird, people watching opportunities.
Along bustling Duval Street at night, extreme costumed revelry of Halloween happens regularly. In such case, odd people watching becomes a major activity.
7. Don’t depend on street signs to get you where you want to go.
Key West lies so far and remote from civilization so why bother to read the confusing distance and directional signs.
8. The feline species evolves freakishly here.
What genetic anomaly occurring at Ernest Hemingway’s Mansion would produce a cat with six toes?
9. Creative marketing strategies stretch intellectual limits of the human mind.
Never discard your auto as junk in Key West. It might make a good advertising display. Boldly pink colors accompanied by distorted fairy tale sculptures also make a good combination for business running appeal.
10. So many cruise boat tourists leave Key West blind to the natural beauty of sky meets sea.
My wife and I gazed at this magnificent Key West sunset as fellow cruise goers surrounded us at the bar scene on ship indulging mindlessly in alcoholic bliss.
Serious Tourist Tip:
It’s much more relaxing to arrive in Key West by cruise rather than car. The arduous drive south from Miami through the full length of the Keys takes it’s toll on one’s physical/mental stability.
Resources:
Snippets of a Traveling Mind 
Great blog. I love how you captured the unusual spots. You know, I have never checked out the cemetery there.. Thanks for reminding me of the little treasures that are so close to home. Wonderful pictures too!
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Hi Leslie: I have been influenced by a travel website called Atlas Obscura to focus on less obvious sites. Happy Holidays.
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I’ve been to Key West several times and loved it! It’s definitely a unique and quaint little city. I went there during their October Fantasy Fest – awesome! Merry Christmas!
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Merry Christmas to you as well.
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🙂
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