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

icon 2 hours Mobile ticket Free Cancellation
Tickets from € 29.25

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

75 King St, St. Augustine, FL 32084, Verenigde Staten Guide will meet guests at the fountain in the front courtyard of the Lightner Museum in between the museum and Flagler College.

Return Details

75 King St, St. Augustine, FL 32084, Verenigde Staten Guide will meet guests at the fountain in the front courtyard of the Lightner Museum in between the museum and Flagler College.

  • Lightner Museum, St. Augustine, Florida, United States
    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.
    10 minutes
  • Flagler College, St. Augustine, Florida, United States
    Location of the old Ponce de Leon Hotel, built by Henry Flagler. This was the epitome of luxury and decadence during the Gilded Age.
    10 minutes
  • St. George Street, St. Augustine, Florida, United States
    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.
    10 minutes
  • Plaza de la Constitucion, St. Augustine, Florida, United States
    From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).
    10 minutes
  • 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
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
dmthibodeau
06 Apr 2023
We had a wonderful personal tour with Ann. She was passionate and very knowledgeable about the wicked ways of St. Augustine. She was able to answer any question we threw at her. We were less than thrilled about not knowing how long the tour actually was. It's advertised as a hour and a half when actually it was three hours. That's a long time. She did condense the tour so we were thankful for that.
suannef2023
21 Mar 2023
We had a wonderful personal tour with Ann, who authored the book “Wicked St.Augustine”. Ann was personable, informative and provided great detail of St. Augustine’s history like we have never heard before. Don’t miss the opportunity to take this tour! Thank you Ann!
Hannah_S
17 Mar 2023
What a wealth of knowledge Ann is! She knows so much and her passion is evident. Could have streamlined the presentation a bit for time’s sake (it’s closer to 3 hrs. than the stated 1.5h). Turns out Mr. Flagler is a real piece of work- was great to hear the real story!
This tour in Florida is organized by Spyglass Travel

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