Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City | 1 hour 30 minutes

80 Reviews | St Augustine
From $30.00 per person Lowest Price Guarantee
Select Date and Travelers
You can select up to 13 travelers in total.
Adult (18-99) Minimum: 1, Maximum: 13
2
Free Cancellation For a full refund, cancel at least 24 hours before the scheduled departure time.
Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
2 Adults x $30.00
$60.00
Approx Total
$60.00

Inclusions / Exclusions

  • Mobile ticket
  • Offered in: English
  • Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'

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.

Meeting points

Guide will meet guests at the fountain in the front courtyard of the Lightner Museum in between the museum and Flagler College.

End point

This activity ends back at the meeting point.

Itinerary

  • 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.

    10 minutes

  • 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.

    10 minutes

  • 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.

    10 minutes

  • 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).

    10 minutes

Sample Menu

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

Free Cancellation

April 26100% refund
April 27No refund

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Reviews

4.9

80 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews
  • 5 stars
    73
  • 4 stars
    4
  • 3 stars
    1
  • 2 stars
    2
  • 1 star
    0

Reviews by TravelOne travelers

Showing 1-5 of 73 reviews with 5 stars

Best tour in St Augustine

Published on 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.

Interesting and entertaining tour

Published on 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.

Enjoyable

Published on Sep, 2024

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

History buff treat

Published on 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.

Unique Experience

Published on Jun, 2024

Very informative and fun! Ann will take as long as you want and give you as much history as you wish. She’s a great storyteller. You get to hear the history you wont hear about anywhere else. Highly recommend!

Compare Similar Experiences

Current

time

1 hour 30 minutes

time Free Cancellation
80
From
$30 /   Person
time

1 hour 30 minutes

time Free Cancellation
1,088
From
$175 /   Group
time

1 hour

time Free Cancellation
124
From
$29 /   Person
time

1 hour 15 minutes

time Free Cancellation
105
From
$39 /   Person
time

30 minutes to 45 minutes

time Free Cancellation
102
From
$81 /   Person
time

30 minutes to 45 minutes

time Free Cancellation
98
From
$39 /   Person
time

1 hour

time Free Cancellation
58
From
$200 /   Group
Likely To Sell Out
time

45 minutes to 1 hour

time Free Cancellation
46
From
$225 /   Group
time

2 hours

time Free Cancellation
12
From
$99 /   Person
Customers Who Bought This Tour Also Bought
time

1 hour 30 minutes

time Free Cancellation
1,088
From
$175 /   Group
Likely To Sell Out
time

1 hour 30 minutes

time Free Cancellation
1,033
From
$46 /   Person
time

1 hour

time Free Cancellation
891
From
$36 /   Person
time

2 hours

time Free Cancellation
802
From
$65 /   Person
time

1 hour 30 minutes

time Free Cancellation
652
From
$39 /   Person
time

1 hour 15 minutes

time Free Cancellation
363
From
$45 /   Person
Likely To Sell Out
time

1 hour 30 minutes

time Free Cancellation
345
From
$49 /   Person
time

1 hour to 12 hours

time Free Cancellation
264
From
$66 /   Person
time

2 hours 30 minutes

time Free Cancellation
227
From
$27 /   Person
Likely To Sell Out
time

1 hour 30 minutes

time Free Cancellation
224
From
$38 /   Person
time

1 hour 30 minutes

time Free Cancellation
224
From
$47 /   Person
time

1 hour to 1 hour 10 minutes

time Free Cancellation
158
From
$20 /   Person
Recently Viewed
time

7 hours

time Free Cancellation
13
From
$247 /   Person
New On TravelOne
time

4 hours

time Free Cancellation
4
From
$1,187 /   Group
New On TravelOne
time

2 hours to 3 hours

time Free Cancellation
0
From
$39 /   Person
time

4 hours to 5 hours

time Free Cancellation
112
From
$48 /   Person
time

3 hours

time Free Cancellation
1
From
$41 /   Person
time

8 hours to 10 hours

time Free Cancellation
0
From
$110 /   Person
time

4 hours

time Free Cancellation
0
From
$90 /   Person
time

14 hours

time Free Cancellation
58
From
$576 /   Person
Connect with TravelOne
Louise Berg
Destination Expert
TravelOne Subscribe
We organise unforgettable vacations.
Subscribe for trending deals.
© Copyright 2025 TravelOne Technologies Inc. | All Rights Reserved.
Visa Card Mastercard Maestro Amex Discover

TravelOne uses cookies to give you the best possible service. If you continue browsing, you agree to the use of cookies. More details can be found in our privacy policy.

Do you have a destination in mind, or would you like TravelOne AI to suggest one?

What is your destination?

City Breakup

Remove
+ Add New

Choose Travel Dates / Flexible and Fixed / Number of Days

What's your ideal trip length?

Days

Your trip length is 0 day


Travel Dates / Flexible and Fixed / Number of Days


Adults
Ages 12 or above
Child
Ages 8-12
Child
Ages 3-7
Infant
Ages 0-2
Adults
Ages 12 or above
Child
Ages 8-12
Child
Ages 3-7
Infant
Ages 0-2

Preferred Star Rating?

Accommodation Preferences

Property Preference?

Accommodation Preferences

Property Location?

Accommodation Preferences

Preferred Hotel Chain?

Accommodation Preferences

Meal At The Hotel?

Accommodation Preferences

What are your meal preferences?

Dining Preferences

What are your preferences for arrival/departure transfers?

Transfers & Internal Transportation

What are your preferences for internal transfers?

Transfers & Internal Transportation

Are you celebrating any special occasion?

Travel Activities & Experiences

Loading questions for you...! Please wait...!

Loading questions for you...! Please wait...!