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.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels, comfortable walking shoes recommended
Wildlife
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.
Spyglass 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.
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.
Tours Offered
4 Tours
History, ghost, and specialty tours
Tour Length
90 Minutes
Standard duration for every tour
Small Groups
Available
Included on the Guided History Tour
Paranormal Expert
Seasoned Investigator
Ghost tour led by a paranormal investigator
Secure spots for haunted history, specialty walking tours, or guided history walks — limited capacity on walking routes.
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.
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
Water bottle
Stay hydrated during the walking tour.
Camera or smartphone
Capture the historic sights and atmospheric streets.