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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

Sun 10 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Sun 10 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)

James_T

Jun 2022

Nice tour guide with interesting stories, but some of her details were historically inaccurate. Also, her presentation was a little too political: I felt like I was sitting in a Feminist Studies lecture (i.e., men bad, women enslaved and degraded by men from 1565 through 1970s).

Response from Host

Jul 2022

So sorry you were a bit disappointed with the experience. The author, also the guide, has painstakingly researched the subject. Thank you for taking the time to review this tour, it helps us be better in the future. Have a great rest of your experience here in our city.

davidzD4341ZO

May 2022

This is my third St Augustine tour and definitely the best. I loved all of the detailed history that can only be found at Wicked St. Augustine.

Response from Host

May 2022

So glad you enjoyed the experience. Yes, Wicked gives history you won't hear anywhere else. And of course ALL of our tours are dog friendly!

B6791UBsamanthas

May 2022

What a great and unique experience! This tour is not like the other cookie cutter tours. The tour guide is the actual author of Wicked St Augustine, so it's literally from the source! You can tell she is very thorough and passionate about her research for the book and tour. I hope more people can learn about the wicked part of St. Augustine and pass it on! Thank you again Ann! 10/10!

Response from Host

May 2022

Agreed! Ann does a great job of telling much of the 'rest of the story' those things you won't hear anywhere else. And yes, she literally 'wrote the book'!