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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

Sun 10 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Sun 10 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)

G6241OCdanag

May 2022

By far, the best way to get the full picture of the history of this city! Highly recommend. A must for all visitors!

Response from Host

May 2022

Thank you so much for the review and the recommendation. So glad you enjoyed the experience.

mc_parris

May 2022

My wife and I enjoyed learning many fun history facts on the St Augustine area. Tour guide was in period costume, friendly and knowledgeable.

Response from Host

May 2022

Thank you for sharing, and glad you enjoyed the experience. Have a great rest of your vacation!

Sharkgteresa

Apr 2022

Ann was a wonderful with orator and storyteller! She was quite knowledgeable about all St Augustine history but focused on the hidden and darker side of the build up of the city. She also gave the history from a woman perspective and told through women s experiences of the time, which we found refreshing! We also took a more general historical tour and it was quite interesting to compare the accounts! We recommend this tour if you want to round out your point of view regarding womens' role in the success of st augustine!

Response from Host

Apr 2022

We're so glad you enjoyed the experience. Yes, Ann gives a refreshing view of our history and covers many subjects not highlighted by mainstream history. Thank you for taking time to share your thoughts.