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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

Sat 09 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Sat 09 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)

395triciad

Oct 2022

I am so glad St. Augustine is honoring the truth of their past and offering such a great historical tour. I learned so much fascinating history that I never would have guessed. Our guide is incredibly passionate and incredibly knowledgeable about both big and small tidbits. Ask a question... She has the answer. Our tour was pleasantly intimate (my sister and I were the only people on the tour). Talk about a front seat pass. I definitely recommend this tour to everyone. A must do while in St. Augustine.

Response from Host

Oct 2022

Not all history is in the light of day, sometimes the most intriguing stories are in the shadows. Ann does a fantastic job, thank you for the kind review.

706triciar

Oct 2022

A MUST DO IN ST. AUGUSTINE! Last night we had the pleasure of a personal tour with the author of the book Wicked St. Augustine! We learned all the facts about the brothels, gambling, and bootleggers of St. Augustine! So fascinating! So much history that is not covered in other tours. Excellent history lesson! I had to buy the book!

Response from Host

Oct 2022

Ann is passionate about the subject matter which is seldom covered in other offerings. So glad you enjoyed the experience, and thank you for the recommendation as well.

kendra g

Sep 2022

Very informative. Had a great time. It was raining and she tried her best to keep us dry, safe, and still going so we didn’t miss anything.

Response from Host

Sep 2022

Thanks so much. The one factor we cannot control is they unpredictable weather. I'm sure Ann did her best to look out for everyone. She is a great storyteller as I'm sure you got to experience in spite of the weather. Thank you for sharing.