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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 18 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 18 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)

Erin_P

Jun 2023

Ann Colby's book, Wicked St Augustine was what led us to this tour. She is a wealth of knowledge on St Augustine, but the seedy bits are her specialty. She gives a very informative tour, sites her sources and this all leads to the tour lasting longer than advertised. The walking isn't very far, a few city blocks. I love history and the stories behind the community I'm visiting. This tour was worth every penny.

Response from Host

Jun 2023

So glad you enjoyed the experience. Ann is very passionate about the material and does a great job of story telling. Enjoy the rest of your time here in our city!

lisatD490MN

Jun 2023

My husband and I thoroughly enjoyed Ann's story telling, her clothing and persona. What a passion she has for this city and this subject. She obviously has done a lot of homework and we both look forward to reading the book. We were the only people with her that night, so the personalized tour was perfect!

Response from Host

Jun 2023

Thank you for the kind words. We are so happy you enjoyed the experience. This type of history is often ignored but Ann shines a light into the dark spaces of the city's history.

ecpreys

Jun 2023

My friend and I were the only guests. I had just read Ann Colby's (the guide) book and was very happy to see there is a tour. Ms Colby has done an immense amount of research and can tell you anything about St Augustine. That said, the seedy bits are her specialty. The tour is longer than advertised and worth every penny. The amount of walking is minimal, a few city blocks. Ms Colby is personable and funny. Take the tour.

Response from Host

Jun 2023

Yes, she literally wrote the book. We are so happy you enjoyed the tour, and thank you so much for the recommendation. Have a great time here!