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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

Wed 13 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Wed 13 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).

Show 1 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (38)

Seaside48043034075

Mar 2022

BEST TOUR EVER!!! So fascinating!! Ann’s passion for history is infectious. Not only does she know her stuff— she is a bona fide historian! All of the information that she shared was from her own discoveries from years of archival research. She brings the characters of history to life! Not only that, she had an in-depth answer to every possible question we could ask. Thank you Ann!!!

Response from Host

Mar 2022

We are so glad you enjoyed the experience, she is quite a dynamic presenter. Your evaluation was absolutely correct in our opinion as well. Thanks again.

Dee K

Mar 2022

We had a fabulous time touring with Ann Colby who has an extensive knowledge base due her diligent research and long time residency in St. Augustine. She has a passion for what she does and it shows. She is also the author of the book, Wicked, St. Augustine which is an extremely helpful read before you go on the tour. We enjoyed it immensely.

Response from Host

Mar 2022

Ann is a tremendous presenter, researcher and tour guide. She has done a fabulous job with the Wicked St. Augustine book and experience. Thank you so much for the kind words.

paulwB7206HE

Mar 2022

Have been visiting SA for years and never had a clue about the other, more interesting, side of the city's history. Our guide, Ann Colby, had herself done the research and made the subject come alive...almost as if she had lived it.

Response from Host

Mar 2022

She does a fantastic job of bringing this hidden history to life. So glad you enjoyed the experience. Thank you so much for the kind words.