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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

New York City Tours

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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).

Show 1 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (38)

ginahT7610DP

Dec 2021

Blanche was our Tour Guide for the evening. She was very nice and a well knowledgable Guide. This tour is all about the real people of St. Augustine and not just the rich. Been on many Tours throughout the USA and I have to say this is one of the best and highly recommend. You will be not be disappointed and well worth the money!

Response from Host

Dec 2021

Awesome! So glad you enjoyed the experience. She is quite the character and enjoys sharing this seldom spoken of history of our city.

annmU8165ZY

Nov 2021

This was more of an extended talk than a tour. Would have been better with the talk delivered while walking and viewing the various locations of previous historic buildings discussed in the talk. Entire event was too long. The information could have been delivered more succinctly with fewer digressions. At first it was interesting but as the presenter droned on, it became tedious.

Response from Host

Nov 2021

I'm not sure which tour you were on, we didn't operate this tour on Nov 15th. We ask that you remove this review due to this fact. Thank you.

655carlah

Oct 2021

This was a really interesting tour! We were fortunate enough to take the tour on a night that Ann Colby, author of Wicked St. Augustine, was the tour guide. You could tell she was an expert on the subject matter and she was very informative and entertaining. This is historical information that you won't learn from ordinary history or text books. But it is important history that helped mold St. Augustine from it's early beginnings up until the middle of the 20th century. If your are going to St. Augustine, this tour should be on your "must do" list. It was great fun for my wife and I. Meeting Ann was a true pleasure!

Response from Host

Oct 2021

Thank you so much for the kind words. Ann is a fantastic story teller and brings the experience to life with her knowledge and presentation. We feel this is an important untold history as well!