Old Jail Museum St Augustine, FL

Built in 1891 and funded by railroad magnate Henry Flagler, the Old Jail Museum in St Augustine offers a compelling glimpse into the gritty side of Florida's past. Though it housed some of the region's most notorious inmates for over 60 years, the jail's exterior—designed in Romanesque Revival style—looks more like a resort than a maximum-security facility. The restored structure still closely resembles its original appearance from over a century ago.

This imposing landmark served as the St Johns County jail until 1953 and was once overseen by one of the toughest wardens in the South: Sheriff Joe Perry. Known for his harsh discipline, Sheriff Perry not only ran the jail but lived with his family just steps from the cellblocks.

On the 30-minute guided tour, led by costumed interpreters, explore the men's and women's cells, the sheriff's living quarters, and the gallows where executions were carried out. Exhibits feature 19th-century judicial practices, early punishment methods, and a unique collection of weapons and historical artifacts.

This immersive tour is as educational as it is entertaining. Families enjoy the interactive elements like trying to "escape" from a cell block for a fun photo op, while history buffs appreciate the authentic stories and preserved architecture. Located near the heart of St Augustine, the Old Jail Museum remains one of the city's most engaging and unexpected historic attractions.