Key West is an entity unto itself and this is one of the many reasons why it has earned the very apt nickname, Key Weird.
There really is no place quite like it. From the picture perfect New England style houses and white picket fences to the rapturous musical offerings heard all over Duval Street every evening, Key West is a treasure trove of paradoxes.
Think palm tree lined streets thrown together with shipped wreck themed museums, cemeteries as tourist attractions and an odd assemblage of supposedly haunted buildings.
It was a paradise-like hideaway for famous faces such as writer Ernest Hemingway and President Truman but is also an attractive playground for misfits from all over the world looking to bask in its unique Floridian fantasy.
Historically, the island was named ‘bone island’ when first discovered having been a burial ground for native Indians. This is the reason, according to many long-term residents, that the prime Florida Key is the location for some spectacularly weird goings on from body-snatching and tragic deaths to haunted dolls (more on that later!).
There is something genuinely fascinating about all of the dark and quirky history that lingers under the surface of this picture-perfect seaside town which is why there is no better place to get truly weird (and have fun!).
Go on a haunted walking tour
When we stumbled upon a brochure for a haunted walking tour of Key West, we decided last minute (with the assistance of two glasses of wine) that we simply had to do it.
We rocked up at 9pm to meet our guide Ted and about twenty other eager ghost-hunters to revel in the dark history of Key West. While we did not know what to expect, the tour took us down dimly lit alleyways and gave us insight into the truly bonkers history of the area.
Ted was an exceptional storyteller armed with a book full of ghostly pictures snapped on his tours, several ghost-detecting devices and a dry humour to keep the atmosphere from getting too dark.
Stories included that of Count Von Cosel, the true life tale of a man who fell madly involve with a young Cuban-American woman. He was so in love that when she passed away immaturely, he embalmed her body and continued to live with his corpse bride for several years in Key West before being arrested. And there’s also the story of Key West Theatre, pictured above, a former Baptist church and the setting of a tragic fire in the 1880’s. According to local legend, the pastor at the time is said to have purposefully set the fire with his own wife and local children inside when it became painfully apparent that he was being cheated on.
Even if you are a skeptic and don’t believe in ghosts, the true life tales from Key West will do enough to send a shiver down your spine or at least pique your interest. The Key West Ghost and Mysteries Tour runs every night at 9pm from the Porter Mansion on the corner of Duval and Caroline Street and lasts about 90 minutes. It is $18 USD for adults and $10 USD for children.
Visit Robert, the haunted doll
Another story that captured our attention on our haunted walking tour was the story of Robert the Doll.
The doll originally belonged to Robert Eugene Otto, a local Key Westian and artist, who was gifted it as a young boy. There are two theories about the origins of the doll. The slightly more absurd version tells the tale of the Otto family maid creating the doll and instilling in him some weird voodoo magic. The generally accepted alternate version is that the doll was purchased in Germany by Robert’s grandfather and given to him.
Here is where both stories converge and it becomes apparent that the young Robert became completely obsessed with the doll and took him everywhere. Soon of course, strange things began happening in the family home in Key West and little Robert insisted that everything was the fault of Robert the doll.
As Robert Gene Otto grew up the doll remained in his custody at the stately Artist House in Key West. When Robert and his wife died, the house and doll passed to a new owner who managed a guest house on the property. The owner and guests swore that strange things happened around Robert, that he often moved around the room he was placed in and many people purported to have seen him staring out the window.
The doll eventually found a new home on exhibit at the Fort East Martello Museum in Key West. It is strongly advised that you ask permission from Robert before snapping a picture of him or you will end up cursed with severe bad luck. Robert receives hundreds of letters a year from past visitors apologising to him for taking unsolicited pictures as their life went bizarrely south afterwards. Weird.
Oh and he is just genuinely creepy. (And I took zero pictures of him. Not today, Robert, not today).
Go on a floating Tiki bar, obviously
Slightly bizarre but hilarious non-the-less are the several floating bars that drift into the harbour at sunset on Key West. These are the Cruisin’ Tikis and their catchphrase is: “Why go bar hoppin’, when you can hop on a bar?” If that doesn’t sell this to you then I don’t know what will.
Set sail on your very own, fully serviced floating bar in the late afternoon and enjoy a cocktail watching the sun go down from the ocean. If the bar itself is not one of the weirder places you have had a drink in your lifetime then I don’t think I can help you.
Have Key Lime Pie everything
Key Lime Pie is a classic of the Florida Keys and is the perfect dessert on a hot summer’s day.
However, Key West does not stop with Key Lime Pie because Key West does not do things by halves. Enjoy Key Lime Pie ice-cream on a stick or Key Lime flavoured cocktails, sweets and pretty much everything in between.
We recommend taking a stroll down Duval Street (pictured above) and make it your mission to find the absolutely weirdest Key Lime flavoured snack you can.
Visit the Cemetery
It is not often that the local cemetery is a bonafide tourist attraction but Key West’s cemetery is literally on most lists of things to do in Key West. While the setting is serene and it is a fine place to spend a hot afternoon, the true attraction to this location is some seriously dark humour.
The Key West cemetery is famous for being the resting place of Ernest Hemingway but mainly for the array of comical one-liners that can be found on many tombstones.
Some gems include “I told you I was sick” and “Jesus Christ, these people are horrible!”. The Historic Florida Keys Foundations does a walking tour of the site twice a week, details of which can be found here.
Take a picture at Southernmost Point of America
Okay this might not seem that weird at first glance, but when we visited the monument that stated itself as the Southernmost Point of the Continental USA (the next stop being Cuba), we were rather surprised to see a queue halfway down the street just to take a photo with this rather unbecoming monument.
Waiting for 30 minutes in the blistering 30 degree heat for a photo did not tickle me pink, so we skipped the queue and I hopped up on a wall to take my own picture and got my own not-so-private snap with the monument.
It was only later that we found out that the Southernmost point is actually not, in fact, the Southernmost point. The actual Southernmost place in Continental USA is located three minutes down the road in an army base that civilians can’t enter .
So yeah, queuing up for a fake monument definitely strikes me as one of the more weird ways to spend your time in Key West.