Where is the meeting point?

Meet at BOG Brewing Co. 218 West King St before the tour start time listed on your booking confirmation.

How long is the tour?

The tour runs approximately 1.5 hours and includes short walking segments and three stop locations.

Is there an age minimum?

There is no specified minimum age, but underage guests cannot participate in alcohol purchases at the brewery stop.

Is the tour wheelchair accessible?

The route includes historic sidewalks and occasional uneven pavement; accessibility may be limited—contact the operator to discuss accommodations.

Will there be a chance to buy drinks?

The itinerary returns to Bog Brewing Company, where attendees may purchase beverages after the tour concludes.

How large are the groups?

Group size is limited to about 25 people to keep the experience intimate and easy to hear.

Brothels & Booze: Exploring St. Augustine's Red-Light District in St. Augustine, FL | History Tour | Guided Tour

On a humid evening in St. Augustine, Florida, Brothels & Booze pulls you into West Augustine's shadowed past. This 1.5-hour walking tour meets at BOG Brewing Co. 218 West King St and follows a compact loop through blocks that once made up the town’s notorious Country Club, the 19th-century center of illegal liquor, gambling, and prostitution. Guided by the author of Wicked St. Augustine, you’ll stand where transactions were arranged with nods and whispers, and hear how vice shaped the city’s economy and social fabric. The tour threads three precise stops: Bog Brewing Company, 218 W King St; Leo C. Chase & Associate's Inc. Funeral Home, 262 W King St; and Sweet City Cupcakes, 233 W King St # A. Each stop is a doorway between present and past—a local brewery with a bawdy backstory, a working funeral home that once operated at the heart of the vice trade, and a small bakery whose storefront masks layers of rumor. The Country Club referenced on the route was not a golf course but a district where demand for illicit services created underground networks that persisted into the 20th century. What makes this experience unique in St. Augustine, the oldest European-established city in the continental United States (founded 1565), is its willingness to examine the city's less-polished chapters. Where typical tours highlight forts and plazas, the Wicked II tour excavates the social history of desire and necessity: madams who supported local economies, illicit liquor that fueled late-night commerce, and gambling rooms that financed other enterprises. It’s storytelling tethered to specific addresses, led by someone who has researched and written about these characters. Practical benefits: the itinerary’s short hops mean minimal walking over historic sidewalks; the final stop returns to Bog Brewing Company for a drink and a debrief; group size tops out at about 25, keeping the experience intimate. This tour is a strong pick for history buffs, social historians, and travelers who prefer their walking tours with grit and a pint. It’s also a vital reminder that urban history is layered—beautiful architecture and culinary spots coexist with stories of exploitation and resilience. Bookers should arrive at the stated meeting point ready to listen, ask questions, and consider how public memory chooses which stories to celebrate and which to bury. Brothels & Booze reframes familiar streets, turning West Augustine into an open-air archive of human commerce, law, and survival. Wear comfortable shoes and expect uneven sidewalks; the guide encourages questions and will point out historic markers. Tickets often sell out for evening slots, so reserve in advance through the booking link. The tour supports local storytellers and businesses, making each purchase a small investment in preserving frank, complicated public histories and context.

About Spyglass Travel

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.