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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

Tue 24 Dec

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Tue 24 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)

Biosafety409

Feb 2022

8 family members took this tour and really enjoyed the experience. The guide is very knowledgeable about St. Augustine history and had obviously done extensive research. I have taken several other tours in the city and never a hint of this part of its history.

Response from Host

Feb 2022

Thank you so much for taking the time and providing this review. We are so glad you all enjoyed the experience. Blanche does a wonderful tour which fills in many voids of our history. Thanks again.

597aliceb

Jan 2022

I'm a recent transplant and now avid local tourist who cannot recommend this engrossing tour highly enough. This fascinating tour places the people and things that mainstream historical narratives seek to erase right at the center of the whole epic story; a story which was exhaustively researched for years using many first-hand sources, and is masterfully told by the ‘Wicked St. Augustine’ author herself, Ann Colby. A perfectly-paced evening stroll at an excellent value ($30 for 90 minutes!), I’ll be taking this tour again and again with all of my future houseguests.

Response from Host

Jan 2022

Thank you so much for the kind words and recommendations. Ms. Ann does a fantastic job of bringing the dark side of St. Augustine squarely into the light. So glad you enjoyed it.

Anita_S

Dec 2021

The enthusiasm of Ann Colby is terrific. She's researched her subjects and conveys the information with gusto!

Response from Host

Jan 2022

Thank you so much. Yes, she is a great storyteller and is passionate about her tour, so glad you enjoyed it!