Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

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 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.

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Location: St Augustine

What's Included

Community Discussion

Q&A

Q: Is there an age limit for this Wicked St. Augustine tour? Thinking about taking my teenage kids.

A: The tour is generally family-friendly, but it does cover some mature themes like gambling and prohibition. It's recommended for ages 12 and up, but you know your kids best. Just be ready to have some conversations afterward since some topics might spark their curiosity!

Q: What should we wear for the Wicked St. Augustine tour? Is it mostly indoors or outdoors?

A: The tour is mostly outdoors, so make sure to dress comfortably and check the weather. Closed-toe shoes are a good idea since you'll be walking around the historic sites. Also, consider layering since it can get cooler in the evenings!

Q: What if it rains on the day of the tour? Can we reschedule?

A: Yes, if the weather doesn’t cooperate, you can usually reschedule with the tour provider. Just reach out to Spyglass Tours as soon as you know. They’re really flexible about changing dates due to weather conditions!

Discussions

Just did the Wicked St. Augustine tour! So worth it!

I took the Wicked St. Augustine tour last weekend, and wow, it was amazing! Our guide had so many cool stories about the hidden history of the city, especially about the speakeasies and the gambling spots. The walking part was enjoyable, and we even got to see some old buildings. I’d definitely recommend it for anyone looking for something unique to do in St. Augustine! Perfect gift idea, too!

Is Wicked St. Augustine a good gift for history lovers?

I’m thinking about gifting the Wicked St. Augustine tour to my dad who’s a huge history buff. I know he loves the stories behind places! Has anyone done this? What did you think? Any tips on making it special?