AFISHA LIFE
St Augustine
Explore
Walking Tours
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 25 Jul

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 25 Jul

Starting at $30.00

Make a reservation

New York City Tours

Unique Activities (21) Transfers & Transportation (175) Tours, Sightseeing & Cruises (252) Entry Tickets (96) Sporting Events (4) Good for Small Groups (27) Seasonal & Holiday Tours (113) Walking Tours (705) Outdoor Activities (48) Limitied Availability Tours (29) LGBT Friendly Tours (9) Family-friendly Activities (8) Wildlife Activities (6) Solo Travelers' Tours (147) Food & Drinks (96) Travelers recommend (174) Good for Groups (32) Top Activities (75) Guided Audio Tours (10) Art, Culture & History (406) Attractions to explore (43) Sustainable Tours (1) Limousine Transfers (5) Donut Walking Tour (2) Virtual Experiences (1) Additional fees (7) DSA non-compliant (17)

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).

Show 1 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (81)

Mattyp9ct

Nov 2022

She was very educated on the subject of all of St. Augustine. And entertaining on top of it! Highly recommended, but be prepared for more than a standard tour. Bring a snack and beverage!

Response from Host

Nov 2022

So glad you enjoyed the experience, yes, she does love the topic and tends to run over a bit. Have a great visit!

395triciad

Oct 2022

I am so glad St. Augustine is honoring the truth of their past and offering such a great historical tour. I learned so much fascinating history that I never would have guessed. Our guide is incredibly passionate and incredibly knowledgeable about both big and small tidbits. Ask a question... She has the answer. Our tour was pleasantly intimate (my sister and I were the only people on the tour). Talk about a front seat pass. I definitely recommend this tour to everyone. A must do while in St. Augustine.

Response from Host

Oct 2022

Not all history is in the light of day, sometimes the most intriguing stories are in the shadows. Ann does a fantastic job, thank you for the kind review.

706triciar

Oct 2022

A MUST DO IN ST. AUGUSTINE! Last night we had the pleasure of a personal tour with the author of the book Wicked St. Augustine! We learned all the facts about the brothels, gambling, and bootleggers of St. Augustine! So fascinating! So much history that is not covered in other tours. Excellent history lesson! I had to buy the book!

Response from Host

Oct 2022

Ann is passionate about the subject matter which is seldom covered in other offerings. So glad you enjoyed the experience, and thank you for the recommendation as well.