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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 15 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 15 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)

Dave H

Mar 2022

I really enjoyed the tour. Learned the entertaining hidden history of St Augustine’s colorful past. This is the stuff you never learn in history books. You’ll go away feeling like you knew many of the town’s elite.

Response from Host

Mar 2022

So glad you enjoyed the experience. Most assured you will not hear this in history books. Darker history is history too!

Susie G

Mar 2022

Ms Ann (or locally known as Blanche:) is extremely knowledgeable about St Augustine and all things bootlegging and “wickedness”. The tour was 2 hours in the evening, not too much walking. In period costume, she made the history interesting and entertaining.

Response from Host

Mar 2022

So glad you enjoyed the experience. "Blanche" is very passionate about this under appreciated history. Thank you so much for taking the time to let us know.

sigler716

Mar 2022

Tour guides knowledge and enthusiasm. We had a wicked funny night. Blanche (Ann) was amazing. We recommend this tour. Adults only😉

Response from Host

Mar 2022

She is such a great storyteller, we agree completely.