Why choose this tour ?

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.



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What makes Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City a unique experience ?

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).

Tour Description & Additional Info:

  • 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


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

Included with Your Ticket

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

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Special Instructions:

    Please be advised..

  • This Tour is Provided by Spyglass Tours.
  • Tour Timezone & Starts at America/New_York.
  • Mobile or paper ticket accepted.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • This Tour is Rated 4.5 Stars based on 80 valid reviews on VIATOR.
  • Minimum 1 Travelers is required to book.
  • Maximum 13 Travelers is accepted for booking.