Haunted St. Augustine: A Spooky City Guide to St. Augustine

A city known for its piratical plunders and the (fictitious) fabled Fountain of Youth, St. Augustine seems like the ideal setting for a ghost story. Though myths and legends do fill the lore of the Ancient City, its haunted history is no tall tale. “The Castillo de San Marcos was built in the late 1600s and witnessed countless battles,” Jan says. “You can only imagine the carnage in and around the building.”

Since the colonization of the area in 1565, St. Augustine has also seen its share of death by murder, mistake, and mysterious circumstance. One need only wander the compact historic district for a few moments before encountering a structure with its own haunted history. Conflicts between soldiers, epidemics among Indigenous peoples, and pirate attacks are the tragic origins of only a few of St. Augustine’s horrific hauntings—and provide the foundation for one of the most haunted cities in America.

Consider Jan’s A Ghostly Encounter tour, during which you’ll learn about local life from the 1500s until today—as well as the dark deaths that created the city’s countless spirits—as a primer for mapping out other sites to explore in St. Augustine. “We want people to love our town as much as we do,” she says. “We’re committed to creating an enjoyable experience for both the living and the deceased.”

So whether you’re searching for the paranormal or simply a photo op, Jan recommends stops at the Oldest Wooden School House, the Old Jail, and the St. Augustine Lighthouse. Of course, the popular pedestrian throughway, St. George Street, is the main vein connecting you to museums, eateries, shops, and haunted history galore. “Go to St. George Street, wear comfortable shoes, and bring a ‘no worries’ attitude’”, she suggests.

What pairs best with the waterside views and homemade crab cakes at O.C. White’s Restaurant, the site of St. Augustine’s first hotel? Terrific tales of supernatural sightings, many of which the restaurant’s manager has experienced first-hand and is all-too-eager to share. After digging into po’boys and jambalaya at Harry’s Seafood, one of Jan’s favorite restaurants, there’s a chance you might bump into the spirit of Isabella in the upstairs washroom. And if you fancy a nightcap from Ann O’Malley’s across from the Huguenot Cemetery, Jan says the pub is packed with mischievous spirits late into the night.

Book a night at the St. Francis Inn and there’s a chance you’ll hear their house servant, Lily, milling about. Don’t dare ask for a glass of milk, though, especially if you’re staying in her former room … Lily took her life many moons ago when her forbidden love affair was uncovered and now haunts the property.

Jan’s also got a soft spot for Elizabeth, the small spirit who haunts the Old City Gate. This charming youth loves interacting with visitors, especially those who stay at “her” house, the St. George Inn.

Thanks to its compact size, you might just spot a specter strolling through any street of the St. Augustine Old City. Jan believes that some spirits are quite fond of her ghost tours, like James, the little boy who hangs out in the Tolomato Cemetery, and Elizabeth, the young girl at the Old City Gate.

Spirits of vengeful prisoners trapped in the Old Jail and claims of Chupacabra sightings at the Tolomato Cemetery are just a few more of the spooky souls within city limits. Though quite morbid, one of Jan’s favorite historical haunts that continues to this day is that of the great Seminole Chief, Osceola, whose head was severed post-mortem and displayed in his physician’s office.