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

The Wicked St. Augustine tour delves into the unwritten history of the nation's oldest city. You will hear stories of the illicit industries that made the town a financial success, all while avoiding the reputation of a sinful city. From its founding St. Augustine had a thriving tavern, gambling and prostitution industry, even while portraying a city founded on religious principles. See the locations of high stakes gambling, speak easy taverns, and private clubs which skirted around the laws of the day, like prohibition. Learn how the political powers knew of these activities, secretly supported their providers, all while keeping a squeaky clean image.

1. 1

   Lightner Museum

   10 min

   The courtyard in front of the old Alcazar Hotel, now the Lightner Museum, also in full view of the old Ponce de Leon Hotel, now Flagler College.

2. 2

   Historic Tours of Flagler College

   10 min

   Location of the old Ponce de Leon Hotel, built by Henry Flagler. This was the epitome of luxury and decadence during the Gilded Age.

3. 3

   St. George Street

   10 min

   Here the stories of the private clubs that lined this and the adjoining streets, gambling halls, speak easies, and boarding houses for upscale vacationers, to the working men of the city.

4. 4

   Plaza de la Constitucion

   10 min

   From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).

• Wheelchair accessible
• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Transportation options are wheelchair accessible
• All areas and surfaces are wheelchair accessible

For a full refund, cancel at least 24 hours before the scheduled departure time.