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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

Fri 04 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 04 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)

suannef2023

Mar 2023

We had a wonderful personal tour with Ann, who authored the book “Wicked St.Augustine”. Ann was personable, informative and provided great detail of St. Augustine’s history like we have never heard before. Don’t miss the opportunity to take this tour! Thank you Ann!

Response from Host

Mar 2023

Agreed! Its amazing how much hidden history exists in this city. She is a passionate story teller we are lucky to have on our team.

Hannah_S

Mar 2023

What a wealth of knowledge Ann is! She knows so much and her passion is evident. Could have streamlined the presentation a bit for time’s sake (it’s closer to 3 hrs. than the stated 1.5h). Turns out Mr. Flagler is a real piece of work- was great to hear the real story!

Response from Host

Mar 2023

Glad you enjoyed the experience. There are always interpretations of Mr. Flagler, a complicated man. Have a great visit.

Carolynthecat

Feb 2023

A great experience. This is a must for history lovers. Get the true lowdown on St. Augustine. Read the book.

Response from Host

Mar 2023

We're so glad you enjoyed the tour and thank you for taking the time to review.