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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

Wed 13 Nov

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Wed 13 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)

Dana_G

Apr 2022

Our guide- Ann Colby- was fantastic! She was a treasure trove of historical facts and presented them in a vibrant manner that brought the past to life. We were spellbound and could have listened to her forever. She presented us with a St. Augustine that we would never have discovered on an ordinary tour: meticulously researched info - sometimes bawdy and outrageous, always startling and fascinating. Also...we recommend buying her book: now used as a text in college curricula, and chock full of delightful facts!

Response from Host

Apr 2022

We are so glad you enjoyed the experience. Ann does a fantastic job of bringing this darker side of our history, out of the shadows and into the light. Thanks for taking the time to spread the word!

judycZ4005VS

Apr 2022

Such an informative evening. We learned so much about St. Augustine that you never hear by taking a trolley or a red train tour. "Blanche" (the alter ego) author of the book, has done extensive research and is willing to share the deep, dark secrets of the Oldest City that you never knew existed. This is not another ghost tour, but an adult-themed, fact-based tour.

Response from Host

Apr 2022

Thank you so much for the kind words. This is definitely something different in our city. Ann does a great job bringing this hidden part of our history to light.

Erin_M

Mar 2022

Our guide was very knowledgeable and passionate. It was great to hear such interesting information to kick off our trip to St. Augustine.

Response from Host

Mar 2022

We agree, Blanche is something special. Thank you for kind words. Have a great rest of your vacation.