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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 04 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 04 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)

Kailey_A

Apr 2023

This was an amazing tour. SO INSIGHTFUL. Ann was incredible. She was so knowledgeable and was an excellent story teller. We were so engaged the entire time. Highly highly recommend if you love history and factual stories.

Response from Host

Apr 2023

We are so glad you enjoyed the experience. Ann is passionate about sharing this little known history of our city. Enjoy the rest of your time here and see you next time.

Dennis_C

Apr 2023

Excellent tour by knowlegable guide that explored a lesser known aspect of St. Aug. I would certainly recommend to other visitors.

Response from Host

Apr 2023

Thank you for the kind words and taking the time to review. It is certainly an area of our history that is under-reported for sure! Have a great time here!

dmthibodeau

Apr 2023

We had a wonderful personal tour with Ann. She was passionate and very knowledgeable about the wicked ways of St. Augustine. She was able to answer any question we threw at her. We were less than thrilled about not knowing how long the tour actually was. It's advertised as a hour and a half when actually it was three hours. That's a long time. She did condense the tour so we were thankful for that.

Response from Host

Apr 2023

We are glad you enjoyed the experience. She is very passionate about the subject matter and tends to run long. Have a great visit here in our city.