St Augustine Bootleggers, Brothels, and Gambling Walking Tour


Free cancellation

A full refund will apply if you cancel more than 24 hours before the activity start time.

Duration2 hours
Guide LanguageEnglish
Good To KnowE-voucher
74 reviews


Whatever history you know of St. Augustine, this tour will teach you about the dark, unwritten side you might not know. The Ancient City has centuries worth of colonial era history and many more predating it, making it ripe for tales that are less than honorable. From the prostitution industry to the secret speakeasy taverns, you’ll learn about the seedy underbelly of St. Augustine’s past and which political powers allowed it to thrive.


A great experience for those who know the city’s traditional history well
See where underground gambling took place at illegal private clubs
Stroll down historic St. George Street
Pass by landmarks like Flagler College and the Lightner Museum


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.
Location of the old Ponce de Leon Hotel, built by Henry Flagler. This was the epitome of luxury and decadence during the Gilded Age.
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.
From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).


Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'

Additional Information

  • 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
  • Suitable for all physical fitness levels

Guide Languages

  • English

Cancellation Policy

  • A full refund will apply if you cancel more than 24 hours before the activity start time.

  • No refund is possible if you cancel less than 24 hours before the activity start time.