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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

Fri 04 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 04 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)

pamelabK4228YG

May 2023

Fascinating tour that provides another, less promoted, dimension of the history and development of the city. “Blanch” (aka Ann Colby) not only provided new insights into the history of the development of the city, but also provided information on the sources she used to gain those insights.

Response from Host

May 2023

She did literally write the book. Glad you enjoyed the experience and thank you for taking the time to share, its a unique experience.

AnthonyA3027

May 2023

Fantastic tour! Highly recommended. Our tour was 2 hours and forty mins. A lot of information about St. Augustine early days. Ann Colby really did her research, she’s a great storyteller!

Response from Host

May 2023

Agreed! Ann is passionate about the subject matter and has done an amazing amount of research into the stories. Thanks for the kind words, have a great time in our city.

Victoria_O

May 2023

The information about Henry Flagler. You don’t hear negative things about him too often in St. Augustine. We really like hearing the history good and bad.

Response from Host

May 2023

Mr. Flagler's legacy in St. Augustine is undeniable, but there will always be those who see it in a different light. Glad you enjoyed the experience, enjoy the rest of your visit.