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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)

vienusw

Dec 2022

What a great tour. We enjoyed it! Great information about another side of st Augustine. Tour lasted longer than scheduled, so we got more than expected.

Response from Host

Dec 2022

We are so glad you enjoyed the experience. Ann does a great job escorting (pun intended) her groups into a part of our history that usually remains in the shadows.

783tracik

Dec 2022

Ann is a extremely knowledgeable tour guide! We learned more on this tour than we did on all of the other St. Augustine tours combined. Ann is so passionate when she speaks and a great historian. She is the author of "Wicked St. Augustine" which we purchased on Amazon and will drive the city today to see more of the locations we spoke about last night. We are from New Orleans and this tour reminded us of home. We loved our time with Ann!

Response from Host

Dec 2022

Thanks so much. She does a great job of sharing our hidden history here in the old city. Have a great visit!

Mattyp9ct

Nov 2022

She was very educated on the subject of all of St. Augustine. And entertaining on top of it! Highly recommended, but be prepared for more than a standard tour. Bring a snack and beverage!

Response from Host

Nov 2022

So glad you enjoyed the experience, yes, she does love the topic and tends to run over a bit. Have a great visit!