Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City invites visitors to delve into the scandalous past of one of America’s oldest cities. This engaging walking tour uncovers the hidden stories that transformed St. Augustine into a thriving hub of clandestine activities, all while maintaining an outward appearance of piety. Participants are guided through the city’s historic streets, where they learn about the bootleggers, brothels, and high-stakes gambling that once flourished behind the Ancient City’s religious facade.

The tour is led by an expert guide who shares captivating tales of how St. Augustine became a financial powerhouse through its thriving underworld. Visitors are taken to the actual locations where speakeasies operated during Prohibition, offering a glimpse into the secretive world of private clubs that skirted the law. The tour also reveals how political powers of the time covertly supported these activities, despite publicly condemning them. This juxtaposition of religious principles and illicit enterprises paints a fascinating picture of a city that embraced taverns, gambling halls, and houses of ill repute.

As participants walk through the city, they stand on the very spots where these historical events unfolded. The tour provides a unique opportunity to experience the city’s past in a tangible way, making the stories come alive. With nearly 100 five-star reviews, Wicked St. Augustine is praised for its engaging narrative and the fresh perspective it offers on the city’s history. This adults-only tour is designed for those who are eager to uncover the wicked truth about St. Augustine and see the city in a whole new light.

Space is limited for this intimate walking experience, ensuring that each participant receives a personalized and immersive tour. To secure a spot on this popular tour, visitors are encouraged to make reservations in advance. For more information and to book a tour, potential visitors can visit the website at https://www.viator.com/tours/St-Augustine/Wicked-St-Augustine-Bootleggers-Brothels-and-Gambling-in-the-Ancient-City/d823-309492P2?pid=P00265653&mcid=42383&medium=link&campaign=SATG.