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

St. Augustine Trip 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.

Additional Info

Duration: 1 hour 30 minutes
Starts: St. Augustine, United States
Trip Category: Cultural & Theme Tours >> Cultural Tours



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What to Expect When Visiting St. Augustine, Florida, United States

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.

Itinerary
This is a typical itinerary for this product

Stop At: Lightner Museum, 75 King St, St. Augustine, FL 32084-4386

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.

Duration: 10 minutes

Stop At: Flagler College, 74 King St, St. Augustine, FL 32084-4342

Location of the old Ponce de Leon Hotel, built by Henry Flagler. This was the epitome of luxury and decadence during the Gilded Age.

Duration: 10 minutes

Stop At: St. George Street, St. George St, St. Augustine, FL 32084

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.

Duration: 10 minutes

Stop At: Plaza de la Constitucion, 1 Cathedral Pl St George Street between King Street and Cathedral Place, St. Augustine, FL 32084

From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).

Duration: 10 minutes



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