Historic Walking Tours in St. Augustine with Spyglass Travel

St. Augustine, Florida, holds the title of the oldest continuously inhabited European-established settlement in the continental United States. Established in 1565, this coastal city brims with layers of American history from Spanish colonial times through the Prohibition era. Spyglass Travel offers a distinctive window into one of St. Augustine’s more shadowed chapters with their guided walking tour, Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City. This is not your typical historical stroll—it’s a sharply focused journey through places where illicit vices once flourished, revealing the city's less talked about but deeply colorful past.

The tour winds through historic streets lined with colonial-era architecture, past hidden taverns and former gambling dens, alongside locations that once housed clandestine operations during the 1920s and beyond. Tour guides bring the underbelly of St. Augustine to life, narrating stories of raucous bootleggers, notorious brothels, and underground gambling rings, mixing detailed local lore with factual history. The Old City’s cobblestone lanes and iron-laced balconies serve as a vivid backdrop, allowing visitors to sense the economic and social tensions that shaped the city’s early modern identity.

Spyglass Travel has crafted a unique niche, blending urban history with an immersive walking experience in an outdoor setting. This activity suits visitors looking to engage actively with St. Augustine’s heritage beyond monuments and museums. By focusing on the city’s “wicked” history, they provide a fresh perspective on how these once-illicit trades affected local culture and development.

The tour's moderate pacing and manageable urban terrain make it accessible to most fitness levels, while the narrative-rich format makes this a standout offering for travelers interested in history with a twist. For those intrigued by American history, urban storytelling, or simply looking for a substantive, outdoor cultural activity in St. Augustine, Spyglass Travel’s Wicked St. Augustine tour offers a compelling, unforgettable experience.