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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 02 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Wed 02 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)

paulettepashwarren

Mar 2024

Not when it’s as interesting and entertaining as Ann Colby’s wicked look at the life and times of St Augustine’s most prominent citizens. Researched and documented, Ann brings the previously unspoken secrets of people and businesses that made the city, naming names and showing places. A treat for tourists that might just be even more fun for locals. Go! Enjoy! We had a great time

Response from Host

Mar 2024

Ann loves to go the extra mile on tours. I'm glad you enjoyed the experience. Have a great visit here in the city!

margaret18499

Feb 2024

This tour is absolutely amazing. Ann Colby our tour guide and author of the book WICKED ST AUGUSTINE is the best. She is a great storyteller who delivers a mesmerizing flawless commentary on life in St Augustine from the first landing of the Spanish right up to the 1960’s. I highly recommend this tour.

Response from Host

Mar 2024

Thank you so much. Ann is very passionate about the subject matter and enjoys sharing with guests. Have a great time in the city!

Melanie_H

Feb 2024

Great experience from an enthusiastic and knowledgeable guide. Things to know: the tour is 3 hours, not 1.5. Also, you only walk a total of a few blocks and sit for most of it. Recommend bringing a lightweight blanket if it's chilly outside. It was truly an EXCELLENT experience. Don't hesitate with this one.

Response from Host

Feb 2024

Ann will tour long, but she does tell you up front and will shorten if requested. Glad you had a great time, thank you for sharing your experience and thank you for the recommendation!