ST. AUGUSTINE HISTORY TOUR FIELD GUIDE
Wicked St. Augustine: Uncovering Bootleggers, Brothels and Gambling in the Ancient City
A focused, 90-minute exploration of St. Augustine’s hidden vice economy that explains how illicit trades shaped the city’s growth.
Wicked St. Augustine: Uncovering Bootleggers, Brothels and Gambling in the Ancient City.
St. Augustine’s layered streets keep more than colonial architecture; they hold a civic history of vice—bootleggers, brothels and gambling—that helped the city exist, prosper and thrive. This concise, interpretive experience guides visitors through those overlooked stories and the ways they fed the Ancient City’s economy and social life.
Highlights
Outing Highlights
Vice as an Engine of Growth
Learn how activities commonly labeled as vice formed a consequential and often hidden part of St. Augustine’s past, contributing to its prosperity and development.
Bootleggers, Brothels and Gambling
The program centers on the city’s oldest profession and associated underground economies—stories of rum-running, houses of ill repute and gaming that shaped daily life.
A Compact, 90-Minute Deep Dive
Delivered in a single, focused session, the experience is deliberately concise—designed to reveal the darker currents of St. Augustine’s past in about an hour and a half.
What the day feels like
What the experience feels like
The program unfolds as a tightly focused historical narrative: a guided traversal of sites and stories that foreground vice as an engine of urban life. Over the course of the session, participants encounter anecdotes and context that link illicit trades to the city’s commercial and social development.
Suitability
Who it's for
Who this experience suits best
Practical planner
Details to review before reserving
90 minutes.
Consult the operator for specific gear guidance; no specific equipment requirements are provided in this summary.
Contact the operator for meeting location and start-time details.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the experience?
The program runs approximately 90 minutes.
What topics does the tour cover?
It examines the history of vice in St. Augustine—bootleggers, brothels and gambling—and how those elements influenced the city’s prosperity.
Is this a history-focused experience?
Yes. The offering is an interpretive, historical look at a specific thread of St. Augustine’s past.
Are there any age or health restrictions?
Participants should consult the operator for any age, health or participation restrictions before booking.
How in-depth is the content?
The experience is a concise, 90-minute deep dive intended to reveal overlooked histories rather than an exhaustive academic treatment.
Where does the experience take place?
The program takes place in St. Augustine, focusing on locations and stories within the Ancient City.