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

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

Thu 03 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Thu 03 Jul

Starting at $30.00

Make a reservation

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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

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.

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.

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.

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)

craiglappin2019

Feb 2023

What a wonderful tour. Very knowledgeable about the wicked history of the city. I learned so much history about the city and about different hotels. This is a must go tour.

Response from Host

Feb 2023

Thank you so very much for the recommendation and the review. I agree, this is a must-see tour. Ann does a fantastic job of shining a light on a dark area of our history.

Samuel_W

Feb 2023

The presenter, a charming local woman, seemed to know everything about the history of St Augustine. She had spent years researching and writing a book about the hidden seedy underbelly of the town, the financiers, the brothel culture, the moonshine industry and speak easies, etc. it is this knowledge that she shares on a 2-3 hour short walk around the core of the town. Mostly sitting with a few short walks between points of interest. It’s easy and entertaining.

Response from Host

Feb 2023

Glad you enjoyed the experience, Ann puts everything into her tour.

Jamie_C

Feb 2023

Ann was excellent! She is a great storyteller, has done her research, and made the wicked passed St. Augustine come to light. We enjoyed our tour and would highly recommend it.

Response from Host

Feb 2023

There is always a history hidden in the shadows, Ann does a great job of shedding light on this often ignored history of our city.