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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 18 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 18 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)

Ashild

Jun 2023

Ann Colby is a fountain of knowledge about both the past and present Wickedness in the Ancient City of St. Augustine. No matter what questions thrown at her, she had a ready answer - as well as COLD water, mosquito spray which kept them at bay and smelled good. Special touches that really speaks to her attention to detail and the customer satisfaction. Highly recommended.

Response from Host

Jul 2023

We agree, Ann is passionate about this, mostly underreported, portion of our city's history. Thank you for the kind review and enjoy the rest of your time here.

divaoftea

Jun 2023

Went as a group of 8 with our family. Guide was knowledgeable, entertaining and humorous. One of the best tours we have ever been on.

Response from Host

Jun 2023

Thank you for those very kind words. Ann enjoys her tours and it shows. Enjoy the rest of your visit to our city!

O4603TJjennifers

Jun 2023

First off, Ann is a master story teller. The Wicked St Augustine tour was my favorite tour of the many I have taken throughout my visits to St Augustine. Ann actually wrote the book that this tour is based on so you get an inside look at all the time and research she put in. I would highly recommend this tour to anyone who wants a true account of the things that went on in this town from the 1500's till the early 1900's. I loved every minute of it.

Response from Host

Jun 2023

Glad you enjoyed the experience. She is a great storyteller and truly loves the content of this often unreported history. Have a great time here!