When I was in Key West about a year ago, I went on the Ghosts and Gravestones Tour. This tour was labeled as the “Key West Frightseeing Tour on the Island of Bones.” The tour began just before dark near Mallory Square where one boarded the Trolley of the Doomed. The old trolley, replete with spider webs and Spanish moss, was led by one of the old Key West historical figures (who miraculously was still living and hosting tours). The trolley weaved in and out of Old Town with tales of scary significance. One such tale was in regards to “Robert the Doll,” who is now permanently displayed at the East Martello Fort (a Civil War fort). Following is the story of Robert (the doll) from Wikipedia:
The doll, which is supposedly cursed, resembles an early 20th-century American sailor. Contrary to popular belief, however, the doll's hair is not made of human hair, but rather, it consists of a synthetic material resembling wool yarn. Supposedly, a little boy named Robert Eugen Otto was given the doll in 1906 by a Bahamian servant who was skilled in black magic and voodoo and was displeased with the family. Soon afterward, the family began to suspect that there was something eerie about the doll. Eugene's parents often heard him carrying on conversations with the doll; at first, they assumed that Eugene was answering himself in a changed voice, but later claimed to have realized that the doll was actually speaking.
Neighbors claimed to have seen the doll moving from window to window when the family was out. Sometimes the doll would emit a terrifying giggle, and the Otto family caught glimpses of it running from room to room. In the night Eugene would scream, and when his parents ran to the room, they would find furniture knocked over and Eugene in bed, looking incredibly scared, telling them that "Robert did it!". In addition, guests claim to have seen Robert's expression change before their eyes and he often blinked.
When Eugene died in 1974, the doll was left in the attic until the house was bought again. The new family included a ten-year old girl, who became Robert's new owner. It was not long before the girl began screaming out in the night, claiming that Robert moved about the room and even attempted to attack her on multiple occasions. More than thirty years later, she still tells interviewers that the doll was alive and wanted to kill her.
The doll is annually rotated to the Old Post Office and Customhouse in October. Strange activity in the museum "supposedly” increases during such times.
As members of the tour, we disembarked at the East Martello Fort to glimpse Robert ourselves. It was dark and eerie at the fort. Robert is housed in his chair in a glass case. I made sure to only think good thoughts about Robert and not let my usual pessimism and skepticism cloud my thinking. I was so careful I didn't even take any pictures. You have to ask Robert for permission to do so. I stood back in amazement and watched my fellow doomed people oblige. I heard that someone disrespected Robert and drove through Alligator Alley later that day and was never seen again. I didn’t want to be cursed by Robert the Doll, believe me, as I still had to drive back through Alligator Alley to Fort Myers to fly home.