Captain Tony's Saloon is housed in the oldest bar in the State of Florida, which was also the site of the original Sloppy Joe's Bar from 1933 to 1937. Key West legend Captain Tony has lived there for most of the last century. He is best known as the owner of Captain Tony's Saloon and everybody but everybody has been in for a beer or two or three from Ernest Hemingway to Shel Silverstein, right on through to Jimmy Buffet who got his start on Captain Tony's stage.Robert the Doll:
Captain Tony's Saloon served not only as a bar, but also as an icehouse and the city morgue from 1852 to 1875 when a hurricane destroyed it. The water washed the bodies together so that they were unidentifiable. The townspeople decided to cremate the bones and place them in bottles that you can find today stuck in the walls of what is now the poolroom.
The large tree that grows through the building and has dangling bras and business cards from it today was the city's hanging tree for murderers and pirates. At least 17 people were hanged from that tree, including a woman who murdered and hacked up her husband and young son. Her spirit now resides in the women's restroom of Captain Tony's. The owner has even taken her picture.
While laying a foundation, Tony uncovered the bones of sixteen bodies and the Elvira tombstone. All were left alone and their spirits are possibly some of those haunting the location today.
One of the most famous island ghost stories surrounds Gene Otto, a painter born in 1900 in The Artist House. At the age of 4, Gene received a doll as a gift. He named the doll, "Robert." From the time he received the doll, Gene's life began to change... and not always for the better. Gene blamed "Robert" for his many misfortunes, and many people who knew the family agreed that "Robert" was indeed responsible for a host of evil deeds. Local legend has it that a Bahamian girl whose exact relation to the family remains one of Robert's many mysteries gave him the doll. Many believe the girl was the daughter of ill-treated servants of the Otto family. Speculation as to his creation include that the doll contains a crystal or was made much like a voodoo doll, thereby creating his evil entity. Whatever his method of creation, Robert appears to be possessed and his ongoing activities continue to be reported.THE LA CONCHA HOTEL:
Otto, an artist who grew up almost inseparable from the doll in a house on Eaton Street (now a bed-and-breakfast), built an attic bedroom for Robert, who would reportedly sit in the windowsill and wave at neighborhood children. It has been said that Robert the Doll was the inspiration for “Chucky” in the movie “Child's Play,” although Robert is much creepier looking. Some people say he resemble everything from Michael Jackson to Curious George.
Otto's wife Anne never particularly cared for the doll and after Otto died in 1974, she rented the house with the stipulation that Robert always stayed in his attic bedroom. The doll, dressed in a white sailor suit, remained in the attic for years and apparently on occasion would move from place to place. Neighbors began reporting hearing an "evil giggle" coming from the attic, some even claimed to hear the doll moving about and peering from the attic window.
After the house was sold, Robert supposedly scared workers trying to renovate the home. One plumber reported that while his back was turned, he heard a child laughing and when he looked around, Robert had moved closer to him. The plumber took off and never finished the job.
Eventually, the notorious doll was removed and placed on display in the East Martello Museum near the Key West airport. To this day, one of Robert's favorite activities is to prevent his photo from being taken. Visitors have reported a variety of camera malfunctions and Robert's favorite trick is to black out his own photo, while leaving the remaining film unharmed. He frequently creates electric and electronic fluctuations and has been said to move his toy lion from one knee to the other and to tap on his glass display case.
But, the attic of the Artist's House was not freed of ghostly presence either... soon after the doll's departure, the ghost of Gene Otto's wife, Anne, took up residence apparently standing guard against the return of Robert's evil spirit.
History comes alive at the Crowne Plaza La Concha. Carl E Aubuchon built this Key West landmark, first opened in January of 1926, to provide the city with a "first class hotel." The newest hotel on the island had 160 rooms, was seven stories high, has marble floors, private baths, elevators and other luxuries that were new to Key West accommodations. It was no surprise that the hotel was an immediate success with wealthy industrialists, visiting dignitaries, and high society.
But like all places full of history, it has its ghosts. Fifteen people have jumped to their deaths from the island's highest building. But none of those seem to be the most active ghost in building, that one is believed to be the ghost of a young man thought to be named Brent who accidentally fell into the service elevator shaft in 1982. Guests have reported feeling someone tap them on the shoulder only to find no one near them.

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