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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

Sat 21 Jun

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Sat 21 Jun

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)

Shelbs0310

Oct 2024

Ann is very knowledgeable and everything she says is based on facts. What makes her tour unique is that she grew up in St. Augustine and has been able to interview individuals who partook in the wicked of the city. She also wrote a book called “Wicked St. Augustine” that is now a textbook at Flagler college. I actually purchased it after the tour. The tour is advertised to be 1.5 hours but can about 3 hours if the parties in the group do not have any obligations. Ann does warn you before the tour about the time.

Response from Host

Oct 2024

Thank you for the kind words. Ann is passionate about the subject matter and is a great storyteller. Have a wonderful time exploring our city!

Jordan_C

Sep 2024

We enjoyed our tour! We learned so much and would deff recommend anyone to take this tour. She was so informative.

Response from Host

Sep 2024

Ann is a fountain of knowledge on the subject matter. Definitely passionate about our wicked history.

Laura S

Jul 2024

This tour was a last minute booking after I experienced this company’s (Spyglass Travel & Tours) Walking History Tour of St Augustine. The guide is the author of “Wicked St. Augustine,” a book that dives into the intriguing, shadow history of the city. This is a one-of-a-kind tour and you will not be disappointed. To say that Ann is passionate about the subject matter is a major under statement. She is an amazing guide, who shares the dark history of the city with story teller flair, but unlike storytelling all she shares is true, verified personally by her through detailed research that includes review of court records and newspaper articles as well as countless interviews. If you love history and intrigue, this is the tour for you, so make the time.

Response from Host

Jul 2024

I knew you would love her tour. It's an underreported part of our history, but important just as well. Thank you for your kind words and enjoy the rest of your visit.