Home to prisoners for over 60 years, the Old Jail in St. Augustine looks more like a resort than a maximum-security facility. The original structure was built in 1891 by Henry Flagler, and although it has been restored and renovated throughout the years, it looks very much the way it did when it opened over a century ago.

Today, you can take a guided tour of the Old Jail, learn about the many prisoners and practices that took place here and see where the Sheriff and his wife and family lived— adjacent to where the prisoners were housed.

Meet Sheriff Joe Perry who had a reputation as being a harsh and strict warden – one of the toughest in the South. Walk through the men’s and women’s cells and see where executions took place in the gallows. Discover the history behind judicial practices in the 19th century and see an array of weapons and artifacts.

Adults and children are thoroughly entertained by costumed actors who portray deputies from the early days and everyone gets a chance to try and escape! The Old Jail is one of just a few prisons of its kind still standing and makes for a great sightseeing and history adventure.