THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
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.
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.
Book with Spyglass Travel
Verified experiences and guided adventures in the surrounding area.
Operated by Spyglass Travel · St. Augustine, Florida
Explore the intriguing underground stories of St. Augustine with Spyglass Travel's Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City walking tour. This private experience offers an immersive journey through the city’s rebellious past, revealing hidden speakeasies, secret gambling halls, and colorful characters from the Prohibition era. As you stroll through historic districts, guides share captivating tales of illicit activity, local legends, and the city’s role in early American history. Perfect for history buffs and adventure seekers alike, this tour combines storytelling with picturesque scenery, making it an unforgettable way to uncover St. Augustine's vibrant past. Whether you're fascinated by the lawless days of the early 20th century or eager to explore historic districts off the beaten path, this experience is designed to entertain and educate in equal measure. Comfortable walking shoes are recommended, and your guide will ensure a safe, engaging exploration of the city's lesser-known stories that bring history to life. Join Spyglass Travel for a private adventure that reveals how St. Augustine became the beacon of both beauty and mischief in Florida's oldest city.
easy.
2–3 hours.
Suitable for most fitness levels, comfortable walking shoes recommended
Yes, the tour is family-friendly, but some stories involve mature themes related to historical illicit activities.
Wear comfortable walking shoes and dress appropriately for the weather; sun protection is recommended in summer.
This is a private tour, tailored solely for your group to ensure an intimate and personalized experience.
There are no strict age restrictions, but parental discretion is advised for younger children due to mature content.
Yes, you can discuss specific interests or questions with your guide to tailor the experience.
Yes, advance booking through Spyglass Travel is recommended to secure your private tour.
St. Augustine was Florida’s first European-established settlement and became known for its lively illegal activities during Prohibition.
The tour promotes awareness of historic preservation and supports sustainable tourism in the city.
Spyglass Travel is a guided-tour operator based in St. Augustine, Florida, that offers immersive 90-minute walking experiences focused on the city’s history and darker stories. The company presents four signature tours: Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City; Ghost Tour of St. Augustine: The Original Haunted History Tour; Walking Guided History Tour of Old St. Augustine; and Walking History Tour of St. Augustine's Historic District. Each tour runs approximately 90 minutes and covers distinct themes — from the city's founding and Gilded Age revival to haunted sites and illicit industries that shaped local life. The Ghost Tour specifically features a seasoned paranormal investigator who shares true ghost stories and demonstrates investigation techniques while visiting locations such as Huguenot and Tolomato Cemeteries. The Walking Guided History Tour emphasizes small group sizes and interactive storytelling to deliver a detailed, personable look at St. Augustine’s evolution. Spyglass Travel’s itineraries include visits to iconic landmarks referenced on tour and narration grounded in historical research and local anecdotes. These guided experiences are designed for visitors seeking both education and entertainment, appealing to history buffs, paranormal enthusiasts, and curious travelers. Booking details, schedules, and current availability are provided by Spyglass Travel for each tour, allowing guests to select the experience that best fits their interests and visit to St. Augustine. Some walking routes cover nearly two miles and visit landmarks such as the Castillo de San Marcos and Flagler College, providing a thorough on-foot exploration of St. Augustine’s architectural and cultural highlights today.
Book with Spyglass Travel