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Wicked St. Augustine
When Pedro Menéndez de Avilés founded St. Augustine in 1565, his New World survival kit included gambling, liquor and ladies for hire. For the next four hundred years, these three industries were vital in keeping the city financially afloat. With the cooperation of law enforcement and politicians, St. Augustine's madams, bootleggers and high-rollers created a veritable Riviera where tourists, especially the wealthy, could indulge in almost every vice and still bring the family along for a wholesome vacation picking oranges and gawking at alligators. Join historian Ann Colby's tour of spots not on the standard tourist map to discover hidden-in-plain-sight bordellos, speakeasies, casinos and the occasional opium den.
131 pages, Kindle Edition
Published February 17, 2020
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Displaying 1 - 2 of 2 reviews
August 1, 2025
What a terrific book! And on such an unexpected subject!
St. Augustine is the oldest continuously occupied city in America. It was founded in 1565 by the Spanish, and it turns out the first arrest for prostitution occurred there in 1566. For the next 400 years, the city was known for its brothels, gambling halls and illicit liquor. Most of these sinful pursuits were designed to cater to the many tourists who arrived there starting in the 1800s.
Sourcing her stories in court records, newspaper accounts and oral histories, author and attorney Ann Colby tracks down the arcane facts behind St. Augustine's wicked reputation. She makes it clear that magnate Henry Flagler made much of this possible by encouraging these "amenities" for the well-to-do customers of his railroads and hotels.
This is no "who won the war" history but one that addresses the way people really lived. The brothels are euphemistically called "boardinghouses" and the madams called "landladies," and they filled the role of providing single women with employment at a time when most jobs were closed to them. One built her own establishment and called it "the Country Club." She offered plenty of liquor and women, and became a pillar of the community.
There are some wonderful yarns to go with the facts Colby has dug up. She relates how one elaborate con -- recounted in court records -- became the inspiration for "The Sting." She also talks about a huge city scandal called "The Police Case," which involved police corruption and resulted in nobody getting punished but everyone being entertained.
My one criticism is that I wish the book had been longer. But I have to say that Colby does a lot with the material she's dug up, and her book will serve as a corrective to anyone who thinks America was a moral and upright nation prior to the 1960s. It definitely was NOT.
St. Augustine is the oldest continuously occupied city in America. It was founded in 1565 by the Spanish, and it turns out the first arrest for prostitution occurred there in 1566. For the next 400 years, the city was known for its brothels, gambling halls and illicit liquor. Most of these sinful pursuits were designed to cater to the many tourists who arrived there starting in the 1800s.
Sourcing her stories in court records, newspaper accounts and oral histories, author and attorney Ann Colby tracks down the arcane facts behind St. Augustine's wicked reputation. She makes it clear that magnate Henry Flagler made much of this possible by encouraging these "amenities" for the well-to-do customers of his railroads and hotels.
This is no "who won the war" history but one that addresses the way people really lived. The brothels are euphemistically called "boardinghouses" and the madams called "landladies," and they filled the role of providing single women with employment at a time when most jobs were closed to them. One built her own establishment and called it "the Country Club." She offered plenty of liquor and women, and became a pillar of the community.
There are some wonderful yarns to go with the facts Colby has dug up. She relates how one elaborate con -- recounted in court records -- became the inspiration for "The Sting." She also talks about a huge city scandal called "The Police Case," which involved police corruption and resulted in nobody getting punished but everyone being entertained.
My one criticism is that I wish the book had been longer. But I have to say that Colby does a lot with the material she's dug up, and her book will serve as a corrective to anyone who thinks America was a moral and upright nation prior to the 1960s. It definitely was NOT.
January 13, 2026
I give this a solid 3.5 ⭐️⭐️⭐️
Wicked St. Augustine – Ann Colby
This was a short, quick read that I enjoyed far more than I expected. Reading about the history of the place where I grew up made the experience especially meaningful. Seeing stories of families I know—and even a mention of my own family—was both surprising and validating.
These are the tales I grew up hearing, passed down through conversations and local lore, and it was incredibly satisfying to see them documented in print. Wicked St. Augustine captures the darker, lesser-known side of the city while preserving the voices and stories that make it what it is. A great read for locals, history lovers, and anyone curious about the stories beneath the surface of this historic town.
Wicked St. Augustine – Ann Colby
This was a short, quick read that I enjoyed far more than I expected. Reading about the history of the place where I grew up made the experience especially meaningful. Seeing stories of families I know—and even a mention of my own family—was both surprising and validating.
These are the tales I grew up hearing, passed down through conversations and local lore, and it was incredibly satisfying to see them documented in print. Wicked St. Augustine captures the darker, lesser-known side of the city while preserving the voices and stories that make it what it is. A great read for locals, history lovers, and anyone curious about the stories beneath the surface of this historic town.
Displaying 1 - 2 of 2 reviews