Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels, comfortable walking shoes recommended
Overview
Discover the daring history of St. Augustine with a private walking tour exploring bootleggers, brothels, and gambling dens. Experience the city's rebellious past through immersive storytelling and scenic streets. Perfect for history lovers seeking an exclusive adventure.
Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
Ages 13+ • 90 Minutes
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About This Adventure
Uncover the intriguing secrets of St. Augustine's past in this 90-minute journey through the city's hidden vices. Discover how the oldest profession shaped the growth and prosperity of this historic locale, revealing a captivating side of history that many overlook. Experience the thrill of exploring St. Augustine's dark legacy.
The Dark Side of St. Augustine History
Duration
90 minutes
About
Learn the history of the oldest city's oldest profession - vice. See how St. Augustine existed, prospered and thrived from this hidden history.
Adventure Tips
Wear comfortable walking shoes
St. Augustine's historic streets may involve uneven surfaces and cobblestones, so sturdy shoes are essential.
Bring a water bottle and sun protection
Florida sun can be strong; stay hydrated and use sunscreen during your tour.
Arrive early for a personalized experience
Arriving 10-15 minutes early ensures you get the most out of your private tour with dedicated attention.
Capture the historic architecture
Bring your camera to photograph the charming buildings and secret spots uncovered during the tour.
Local Insights
Wildlife
- Iguanas in the historic district
- Seagulls along the waterfront
History
St. Augustine was Florida’s first European-established settlement and became known for its lively illegal activities during Prohibition.
Conservation
The tour promotes awareness of historic preservation and supports sustainable tourism in the city.
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Adventure Hotspots in Jacksonville
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Ensures comfort while navigating historic streets and uneven surfaces.
Sun protection (hat, sunscreen)
Protects you from the Florida sun during outdoor exploration.
summer specific
Water bottle
Stay hydrated during the walking tour.
Camera or smartphone
Capture the historic sights and atmospheric streets.