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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

September 10100% refund
September 11No 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.
Traveler Photos
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!

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