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

Overview
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.
City: St Augustine
Fri 04 Jul
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You can choose the date already on the booking website
Starting at $30.00
Fri 04 Jul
Starting at $30.00
Make a reservation
What's Included
Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'
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
What To Expect
1
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.
2
Historic Tours of 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.
3
St. George Street
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
Plaza de la Constitucion
From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).
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Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Traveler Photos
Reviews (81)
Maria M
Feb 2023
Ann is the type of person you meet once in a lifetime. She is the real deal. Her passion and inquisitive nature led her to piece together a narrative of St Augustine’s past that has been hidden-though in plain sight. She took on a monumentally important task. After the tour, you realize that she has impacted St Augustine’s history forever. So honored to have met her and heard the stories directly from her. It is a very interesting tour and was one of the highlights of our stay in St. Augustine. Ann has so many stories and can speak enthusiastically for hours about the ā€œwickedā€ past of this city, but if you have time constraints, she’ll happily accommodate you. The walk itself occurs along King Street and you’ll learn about the history of some of the buildings along the way as well as other notable locations. There’s plenty of opportunities to sit and enjoy the stories Ann shares. You won’t be on your feet the entire time. Great for someone who’s done the other tours and is looking for an eye opener on the city but also equally interesting to us, as first time visitors to the city. My favorite part of this tour is how Ann seamlessly connected the societal impacts of each group that impacted St Augustine.
Response from Host
Feb 2023
Not much else we can add to this review, we agree. Thank you for sharing, enjoy the rest of your visit.
931soro
Feb 2023
This tour is a must if you’re visiting St. Augustine! You learn all the history—the real history. It’s entertaining and informative. Ann is incredibly knowledgeable and tells some of the most interesting, wild stories. This tour was the highlight of my trip. I can’t recommend it enough! If you’re planning on buying her book, bring cash & buy it from Ann herself!
Response from Host
Feb 2023
Thank you for taking time to review. I'm so glad you enjoyed the experience, Ann is a dynamic storyteller and enjoys the tour as much as it seems.
Natasha_B
Jan 2023
Ann was great; visited this weekend, great tour very knowledgeable! Her book was also a great read- enjoyed photos to place to the characters throughout the journey.
Response from Host
Jan 2023
Thank you so much for taking time to share your thoughts. We are so happy you enjoyed the experience. She brings a side of history to life that is seldom revealed.

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