In 1878, oil magnate and industrialist, Henry Flagler, left the familiar confines of his tony and privileged life in New York City and traveled south to Jacksonville, Florida with his ailing wife. On strict doctor’s orders, they were advised to escape the intemperate winter of Manhattan so his wife, Mary Flagler, could potentially recover from tuberculosis. She would not survive the trip. Shortly thereafter, Henry Flagler would re-marry and make his way to the Ancient City, St. Augustine, Florida. Finding the area charming and brimming with possibilities but sorely lacking in accommodations, the businessman hit the ground running and began to make sizable real estate investments, one of which was the Hotel Ponce de Leon.

In 1891, Henry Flagler contracted the company that would eventually build Alcatraz to construct a jail just north of downtown on San Marco Ave. So as not to create an eyesore that would strike fear in the hearts of the general public and to avoid discouraging his fat cat friends from investing in the city, he decided to disguise it.

Listed in the National Registry of Historic Places, The Old Jail is a must-visit when in St. Augustine! Built to look like a hotel in the Romanesque Revival style and painted in an unassuming color, visitors will find that the Old Jail has been renovated to give tourists a glimpse into the daily lives of St. Augustine’s most notorious prisoners living under the penal system of the 19th and early 20th centuries. Costumed actors tell tales of the jail and its occupants, and even book you as an inmate! Additionally, the Old Jail has a large collection of weapons and artifacts for you to inspect up close and is one of just a few prisons of its kind still standing that makes for a great day of sightseeing on a historical adventure. It would be a crime if you didn’t stop by for a visit! You can also have an encounter in the Old Jail on a St Augustine ghost tour.

Get ready to #VacayYourWay with Old Town Trolley in St. Augustine! Treat yourself to the relaxing vacation you deserve, whether you’re a history buff, a sightseer, or an adventurous family. From the Castillo de San Marcos to the Fountain of Youth and everywhere in between, see the best of the Ancient City with live narration from our friendly and knowledgeable guides.