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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

Mon 23 Dec

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Mon 23 Dec

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)

tianao529

Oct 2021

If you are into history, you will appreciate learning about the hidden history of the city, of the rich and famous, of the women's role in society over time. If you are not into history, you will enjoy the evening walk around town listening to vivid stories that will transport you back in time. Ann, our tour guide, was dressed in a gown from an old era, and her antique lantern illuminated the path ahead. Sometimes, when guides dress up, they compensate for a lack of substance in their tours with such a gimmick. But Ann was all substance - a lawyer by trade, she engaged in deep research to develop content for this tour and even wrote a book on the topics you'll hear about. This tour changed my understanding of not only St. Augustine's history, but the US history as well. I highly recommend it.

Response from Host

Oct 2021

Thank you so much for the kind words. Yes, Ann is a great story teller, she really brings her book to life. This hidden history deserves the light of day, finally!

M4620MEtonyc

Sep 2021

The guide was great, very knowledgeable, made the tour extremely interesting. It is a tour you do not want to miss.

Response from Host

Sep 2021

Great to hear! Yes, we are very proud of this tour. Hope to see you again soon, glad you enjoyed it!

Jodi_M

Sep 2021

The tour started off with problems. We started early and there was one person came up just before the start time she was given. The guide supposedly had been told a different time then the rest of us. The guide told many tales. Most of the time these stories are based on some truth but embellished for effect. But when another person in the group has family with direct contact with the person in the story and no history of such tales one has to wonder about some of the other stories as well. Also at this time I have not found any documentation of said tales. (Still Checking)The guide did say at the end of the tour that this was his first tour on this subject. Would recommend more research. I went on several walking tours while in the city and no other history ever referred to some of his stories.

Response from Host

Sep 2021

So sorry you did not enjoy your experience. Our stories are based on the Wicked St. Augustine book. The stories have been exhaustively researched by the author and we stand behind her research. The subject matter of this tour is not usually covered on most tours, which is what sets it apart.