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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

Sat 09 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Sat 09 Nov

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
Guides required to regularly wash hands

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.

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 (38)

abbyclasper

Aug 2022

This was a great tour and Ann was extremely informative! Overall a great tour and we enjoyed our time.

Response from Host

Aug 2022

We are so glad you enjoyed your evening with Ann, she does a great job of sharing a hidden history of our city.

Stephanie_D

Aug 2022

Wow! We got soooo much more than we bargained for. She spent extra time with us and answered all our questions. She is well researched and definitely engaging! She provides extra information than what was in her book. A truly delightful experience and we will definitely be returning customers.

Response from Host

Aug 2022

Awesome! We are so glad you enjoyed the experience. Ann is very passionate about the subject matter, and it shows.

lcfl

Jul 2022

We were fascinated by Ann Colby's extensive knowledge of St. Augustine. Don't miss this tour. You'll learn about the history of St. Augustine that no one told you about.

Response from Host

Jul 2022

Thank you for taking the time to share you experience. Ann does a great job of shedding light on a portion of history seldom discussed in our city. Thanks again.