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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)

Crystal_M

Jan 2023

Ann Colby was the most informative historic tour guide. Her knowledge and love for St Augustine's history was amazing. Our tour was supposed to 1.5 hours and we ended up spending almost 3 hours with Mrs. Colby. My husand I have been on several tours through out St Augustine. This was by far one of the best. The Wicked history of St Augustine was mind blowing.

Response from Host

Jan 2023

Glad you enjoyed the experience and thank you for sharing your review. She does a great job!

Erin_G

Jan 2023

It was a long tour (longer than advertised) but the time went fast. Really interesting topic. I can’t attest to the accuracy, but it all seemed probable. Would highly recommend, especially if interested in the city’s history.

Response from Host

Jan 2023

Thank you for the kind words. We are pleased you enjoyed the experience and appreciate the recommendation. Have a great visit.

nicholasmG3371AX

Dec 2022

Ann was our tour guide and she did a great job! She was super knowledgeable about the St. Augustine vice industry's history. This tour is a great way to kick off your first night in town because you will learn a lot of things that you will remember on other tours that will frame things in a more family friendly light. We might not have caught some of those family friendly adjustments if we hadn't done this tour first. Highly recommend!

Response from Host

Dec 2022

Awesome! Its great to get another side of history, and the Wicked Tour certainly doesn't disappoint. Ann is truly an amazing storyteller. Have a great visit, and thank you for sharing your thoughts.