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.
What's Included
- Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'
Meeting Location
75 King Street
St. Augustine, FL 32084, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
Lightner Museum
10 minutes Admission Ticket Free
Historic Tours of Flagler College
10 minutes Admission Ticket Free
St. George Street
10 minutes Admission Ticket Free
Plaza de la Constitucion
10 minutes Admission Ticket Free
Additional Info
- Confirmation will be received within 48 hours of booking, subject to availability
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- This tour/activity will have a maximum of 26 travelers
Frequently Asked Questions (8)
Q: What is the cancellation policy for the Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City?
Cancellation Policy
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Activity code: C-309492P2
Traveler Photos
Reviews
Average 4.85 out of 5 stars based on 98 traveler reviews collected by Cool St. Augustine and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (8)
The answers provided below were previously given in response to questions from Cool St. Augustine customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (EST).
- This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
- Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025The minimum age to participate is 18..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City is as follows:
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City will be included in your confirmation email from Cool St. Augustine. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'
Additional Info
- Confirmation will be received within 48 hours of booking, subject to availability
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- This tour/activity will have a maximum of 26 travelers
