Step behind bars and experience St. Augustine's darker history at the Old Jail Museum, one of the few 19th century jails still standing in America. Built in 1891 by oil magnate Henry Flagler, this remarkably preserved facility served as the St. Johns County Jail for over 60 years, housing everyone from petty thieves to hardened criminals. Listed on the National Register of Historic Places, the Old Jail offers a fascinating and often humorous look at frontier justice, prison life, and the surprisingly harsh conditions inmates endured just a short walk from downtown's luxury hotels. The jail's exterior appearance tells an interesting story about Flagler's priorities. While investing millions in creating magnificent hotels like the Ponce de Leon to attract wealthy winter tourists, Flagler needed a secure facility to house criminals without frightening away his clientele. His solution was ingenious. The jail was designed in Romanesque Revival style with an attractive paint scheme, making it look more like a Victorian house than a maximum security prison. Only upon entering do you discover the grim reality behind the pleasant facade. The building was constructed by the Pauly Jail Company of St. Louis, the same firm that would later help build Alcatraz, and their expertise in creating escape-proof facilities is evident throughout. Guided tours depart every 15 to 20 minutes from 9:00 AM throughout the day, and each 30-minute tour is led by costumed actors who bring the jail's