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 20 Jun

Other dates

You can choose the date already on the booking website

Starting at $30.00

Make a reservation

Fri 20 Jun

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)

Kary_K

Feb 2025

You will learn so much! Ann is very entertaining. We got a whole different understanding of the area!

Response from Host

Feb 2025

Awesome! History has several perspectives and Ann's is unique. She does a wonderful job of sharing the shadier side of our history.

Stephanie_C

Dec 2024

What this tour isnt: -Extensive walking tour -Visiting old houses of ill repute(even if some still stand) - A drinking tour - Child friendly - Ghost tour What this tour is: - Informative history about the not so underbelly of st Augustine - Interesting facts about the men (and women), who shaped history and progress in the area. Such as, who had the first ensuite bathrooms?? Not the Uber rich! - Lots of information, lots of sitting or standing if you prefer. I didn't know a lot about the area, so some facts were hard to connect or forgettable. However, the stories and history of the women here, and what they were allowed to do was cool. Who knew such a family friendly city had a former reputation for all the things good peotof faith "don't" do? The irony and humor of our guides presentation was not lost on me! Be prepared for lots of information.

Response from Host

Dec 2024

Thank you for taking the time review. Ann has a passion for the subject matter and does a great job of sharing that passion.

Joe_B

Nov 2024

It was really interesting to hear about some of the REAL happenings in St Augustine. Tour guide was very knowledgeable and a great story teller! Best tour I took while visiting the area.

Response from Host

Nov 2024

Thank you for the kind words. Ann is very passionate about the subject matter; she literally wrote the book on the shadowy side of St. Augustine. Have a great time exploring the rest of the city.