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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 25 Jul
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You can choose the date already on the booking website
Starting at $30.00
Fri 25 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)
Mattyp9ct
Nov 2022
She was very educated on the subject of all of St. Augustine. And entertaining on top of it! Highly recommended, but be prepared for more than a standard tour. Bring a snack and beverage!
Response from Host
Nov 2022
So glad you enjoyed the experience, yes, she does love the topic and tends to run over a bit. Have a great visit!
395triciad
Oct 2022
I am so glad St. Augustine is honoring the truth of their past and offering such a great historical tour. I learned so much fascinating history that I never would have guessed. Our guide is incredibly passionate and incredibly knowledgeable about both big and small tidbits. Ask a question... She has the answer. Our tour was pleasantly intimate (my sister and I were the only people on the tour). Talk about a front seat pass. I definitely recommend this tour to everyone. A must do while in St. Augustine.
Response from Host
Oct 2022
Not all history is in the light of day, sometimes the most intriguing stories are in the shadows. Ann does a fantastic job, thank you for the kind review.
706triciar
Oct 2022
A MUST DO IN ST. AUGUSTINE! Last night we had the pleasure of a personal tour with the author of the book Wicked St. Augustine! We learned all the facts about the brothels, gambling, and bootleggers of St. Augustine! So fascinating! So much history that is not covered in other tours. Excellent history lesson! I had to buy the book!
Response from Host
Oct 2022
Ann is passionate about the subject matter which is seldom covered in other offerings. So glad you enjoyed the experience, and thank you for the recommendation as well.

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