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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)

msholder37

Feb 2024

This was a GREAT tour! Be advised the tour is not 1.5 hours but closer to 3. Having said that, the guide was willing to work with our schedule. You also walk only a few blocks and get sit for most of the tour. The guide was engaging, fun, and knowledgeable. HIGHLY RECOMMENDED. Melanie

Response from Host

Feb 2024

Thank you. Ann does indeed run long, but she is passionate about the subject matter. We appreciate you taking the time to share your review and the recommendation. Have a great time visiting and great to see you again!!!

A748TWdavidj

Sep 2023

Great evening, focusing on the history of a town I thought I knew. Beautiful architecture, great stories from past to present. Our guide was very knowledgeable, but then she did write the book Wicked St. Augustine (Ann Colby). Highly recommend. Warning: it is an Adult only tour and it will probably run more than 90 minutes. Would definitely go again.

Response from Host

Sep 2023

Fantastic! We are so happy you enjoyed the experience into the city's darker history. Thank you for taking the time to review and enjoy the remainder of your visit.

Aubrey_H

Aug 2023

I actually ended up being the only person participating that night so I got a very personal tour! I’m a quiet, awkward person so I was anxious to hear this at first but Ann made me feel comfortable and kept me very engaged with her storytelling skills. It wasn’t what I expected from a tour but as someone very interested in history I was very pleased. I will point out that the length is much longer than advertised but she let me know offhand and mentioned that if I had time restrictions she could condense the tour/information. As I’m solo and had all the time in the world I went with the Real McCoy! (the origins of which you will learn from Ann in the tour.) There was lightening out and Ann made sure to keep an eye out for its distance and keep us near cover in case of rain. She also mentioned that she had cold water and bug spray available! It’s not like other walking tours where you’re moving around constantly — there were about 5 stops and at each you could find somewhere to sit/lean while Ann spoke. I really enjoyed my time and highly recommend to people who are interested in REAL history and not just what they will teach you in school. I ended up buying Ann’s book on kindle when I went home.

Response from Host

Aug 2023

So glad you enjoyed the experience. Yes, Ann takes great care with her tours and guests. She is a great storyteller and literally wrote the book on this subject matter. Thank you for sharing your experience.