Made it back from Vacation the other night.

We’ve been going to Key West for about 7 years. (You can read about our last trip, with my brother Ben, here)

Just love it there. It’s a strange little island that’s been attracting treasure hunters, pirates, Cuban exiles, musicians, artists, writers and even presidents for over 150 years.

A walk down Duval street is a feast for the eyes. We never know who, or what, we’ll see.

One of the most famous bars on the island is Sloppy Joe’s. It’s actually on the National Registry of Historic Places.

We always make a stop there.

Most people don’t know that Sloppy Joe’s used to be across the street in the spot now occupied by Captain Tony’s. (Yes, I realize it says that on the sign…but who reads those?)

On the night of Dec 5, 1937, Sloppy Joe’s owner Joe Russell asked everyone in the bar to help “move” his business to the new location across the street……rather than pay the $1 a month increase in his rent. Even his most famous patron, Ernest Hemingway, joined in – helping himself to a urinal in the men’s room. He said, “I’ve pissed enough of my money into this thing to pay for it.” He took it home with him where his humiliated wife Pauline had it converted into a fountain. (It’s still there today, btw)

Captain Tony Tarracino took over the location, with his bar Captain Tony’s, in 1961.

Tony dropped out of school in 9th grade to sell whiskey during Prohibition. Before becoming a bar-keep, he was a shrimper, a charter boat captain, and a gun runner. He was married 4 times – outliving his first 3 wives – and fathered 13 children. Tony ran for mayor of Key West 4 times before winning the 1988 election by only 32 votes.

His stance was to keep Key West a refuge for eccentrics and renegades. He only lasted in office 2 years.

“Best 2 years of my life”, he said.

Even though Tony sold the bar in 1989, it retained his name……and he could be found drinking there every day.

It’s got a lot of……….character.

The bar stools are commemorated with the names of the celebrities who sat in them……we got Ted Kennedy and Jerry Seinfeld,

The bar is centered around the island’s “hanging tree”, 17 people are reported to have been hanged in it. It grows straight through the roof and even has the grave marker of a Reba Sawyer under it.

Hard to believe that this was our first time in Captain Tony’s…..but we’ll be back. (Even though the place smells exactly like it looks like it would………. like “tinkle”)

Everyone who’s ever visited Key West will agree that the Caribbean sunsets are spectacular, and the best place to watch those sunsets is from Mallory Square.

Every evening, about an hour or so before sunset, the square fills with tourists eager for that spectacular view.

Luckily, to entertain those flocks of tourists, there are street performers offering free shows. (Most involving fire, or balancing, and usually both at the same time)

The festival began in the late 60’s as the island hippies would gather nightly on the pier to “smoke” and watch the view. Over the years tourists began joining them and eventually local vendors set up card tables and the street performers followed quickly behind. When nearby merchants began complaining, the city was forced to intervene. The vendors and performers, joined by Captain Tony of course, formed the Key West Cultural Preservation Society to insure that the nightly celebration would continue……and it still does.

I know, most of the performers look like former/current members of the Red Hot Chili Peppers. But they certainly know how to put on a show.

“And how was the sunset?” you may ask.

What do you think?

Breathtaking…….

Definitely worth checking out.

Key West has had an odd-ball cast of famous residents over the years – Jimmy Buffet, Hunter S Thompson, Truman Capote, Earnest Hemingway, Calvin Klein, Judy Blume, David Allen Coe, Mel Fisher, Robert Frost, Harry Truman, Kenny Chesney, Tennessee Williams, Shel Silverstein…….

…….but certainly none more memorable, or creepy, than Robert the Doll.

Robert Eugene Otto was given “Robert” the doll when he was a small boy. As the story goes, the doll was made by a family servant – skilled in the black art of voodoo, who was displeased with the Otto family. Immediately, the family noticed that Robert the doll brought some strange occurrences with him. He moved from room to room, all by himself. Young Gene would talk to Robert, and the family would hear the doll answer him back…….and sometimes even giggle. Whenever some mischief was performed, like rearranging heavy furniture in the middle of the night, Gene would always say, “Robert did it.”

Gene carried the doll everywhere with him, well into his adulthood. When he married Anne, his new bride had no idea that Robert wouldn’t like her.

….and he didn’t.

Robert would play mean-spirited tricks on her, like hiding her favorite earings, and her new husband’s excuse was always the same, “Robert did it.”

But when Robert locked her in a closet for several hours, she insisted that the doll be kept in the attic in retaliation. Gene grudgingly obliged and set Robert in one of the attic’s turret windows so he could watch the street.

People walking by the house would swear that he moved from window to window…..and children would claim that he waved at them.

After Gene’s death in 1974, Anne sold the house on the island and Robert the doll with it. The new owners of “the Artist’s House” would hear running, rummaging, and occasionally even giggling coming from the attic where Robert was kept.

The noises only stopped when he was donated to the East Martello Museum.

And that’s where Robert is today, under a locked glass case (to keep him from running around the museum at night and causing mischief, I would suppose).

We always visit him when we’re in Key West.

You can too, but be warned…..

Robert doesn’t like to have his picture taken without asking his permission first. Bad luck follows anyone who would dare to. The wall behind him is filled with cards and letters from unlucky tourists asking his forgiveness.

Don’t worry, we always ask permission first. (Lord knows that we don’t need any bad JU-JU)

Hope ya’ll enjoyed reading about our trip as much as we enjoyed going on it.

Now, go to Key West.