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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 28 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Mon 28 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)

gregoryrP569ZI

Jul 2023

The endless knowledge, presented in a story format, resulted in 3 hours of history being presented while seemingly only spending 1 hour. It did not matter that it rained on and off during the walk.

Response from Host

Jul 2023

Fantastic! Yes, it was a challenging weather night, and we're thrilled you enjoyed the experience. Thank you for the kind words, have a great visit!

williamdN4447YP

Jul 2023

We had a fantastic time with Ann as a guide through the darker side of St Augustine. Very informative and she does not hold back on talking about the color of the town. And soooo much better than being trapped on a bus.

Response from Host

Jul 2023

Agreed! She is fantastic and walking on an intimate tour is far better. Thank you so much for the kind words. Have a great time in our city.

Michelle_S

Jul 2023

We had a lot of fun, she is very knowledgeable and will tell you things the other tours don't. Don't miss this one

Response from Host

Jul 2023

Yes! The darker side of St. Augustine's history is seldom discussed. Have a great visit!