Haunted Florida

St. Augustine & Key West • Updated October 2026

Florida's ghost stories cluster at the two ends of the state, in its two oldest towns. St. Augustine, founded in 1565 by Pedro Menéndez de Avilés, is the oldest continuously occupied European settlement in the United States. Key West, at the end of the Overseas Highway, has been a wreckers' town, a cigar town, a Navy town and a writers' town, and it has kept the dead from all of them. Both run ghost tours every night of the year. Here is what is actually behind the stories.

St. Augustine

The lighthouse and the Pittee girls

The current St. Augustine Lighthouse was built between 1871 and 1874. During construction, the keeper's children and the superintendent's daughters played on a rail cart used to haul supplies up from the water. In 1873 the cart broke loose and ran into Salt Run, the tidal creek at the foot of the hill. Three girls drowned, including two of the Pittee sisters, daughters of superintendent Hezekiah Pittee. Only four-year-old Carrie, the youngest Pittee, survived. Accounts disagree on whether a brake board had been removed or simply failed. The girls are the lighthouse's most famous ghosts: laughter on the stairs, small footprints, a figure in a blue dress at the top of the tower. The lighthouse runs its own nighttime Dark of the Moon tours.

The Castillo and the old city

The Castillo de San Marcos is the oldest masonry fort in the continental United States, built by the Spanish starting in 1672 out of coquina, a local shell-stone that absorbed cannonballs instead of shattering. Its dungeons, the Old Jail on San Marco Avenue, the Tolomato Cemetery and the grand old Ponce de Leon Hotel (now Flagler College) all come with their own stories, and the narrow streets of the old quarter are the best setting for a ghost walk anywhere in the South.

Key West

Robert the Doll

In 1904 a Key West boy named Robert Eugene "Gene" Otto was given a straw-stuffed doll about three feet tall, dressed in a sailor suit. One version of the story says it came from a family servant who practiced voodoo. Gene named the doll after himself and kept it his whole life; neighborhood children said they saw it moving in the turret window of the Otto house on Eaton Street. Gene died in 1974, the house was sold, and the doll eventually went to the Key West Art & Historical Society. Since 2004 Robert has had his own gallery at the Fort East Martello Museum, where the walls are covered in letters from visitors. Many are apologies: people who photographed him without asking permission and then had cameras fail, flights cancelled and worse. The museum's advice, offered with a straight face, is to ask first.

The rest of the island

Key West's cemetery, with its above-ground vaults and famous epitaphs, the old Marine Hospital, the Hemingway House's six-toed cats and the ghost of Captain Tony's Saloon, which was once the city morgue, all feature on the nightly walking tours that leave from Mallory Square and Duval Street.

Robert the Doll: Fort East Martello Museum, 3501 S. Roosevelt Blvd, Key West, next to the airport. Ask before you take his picture.

Daylight plans

Both towns are better in daylight too. In Key West, the ghost tour is the evening; the day belongs to the water. Key West boat tours run reef snorkel trips, sunset sails past Mallory Square, dolphin and backcountry trips into the flats, and fishing charters that leave at dawn. Do the water first, the cemetery second, and Robert last.

Questions people ask

What is the most haunted city in Florida?

St. Augustine is usually given the title. Founded in 1565, it is the oldest continuously occupied European settlement in the United States, with the lighthouse, the Castillo de San Marcos and the Old Jail all claiming resident ghosts. Key West is the other contender.

What happened to the Pittee girls at the St. Augustine Lighthouse?

In 1873, during the lighthouse's construction, a supply cart the children were playing on broke loose and ran into Salt Run. Three girls drowned; only four-year-old Carrie Pittee survived.

Who is Robert the Doll?

A three-foot straw-stuffed doll given to Key West boy Gene Otto in 1904. Gene kept him until his death in 1974. Since 2004 Robert has been displayed at the Fort East Martello Museum in Key West, where visitors leave letters apologizing for photographing him without asking.

Where is Robert the Doll?

Fort East Martello Museum, 3501 S. Roosevelt Blvd, Key West, run by the Key West Art & Historical Society.

Are there ghost tours in Key West and St. Augustine?

Yes, nightly in both. St. Augustine's lighthouse runs its own after-dark tours, and Key West walking tours leave from the Duval Street and Mallory Square area most evenings.