Old Jail (part of Old Town Trolley Tours & Attractions of St. Augustine)

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.

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 public and to avoid discouraging his fat cat friends from investing in the city, he decided to disguise it.

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!

Museum is wheelchair accessible on first floor only.