Brothels & Booze: Exploring St. Augustine’s Red-Light district

Explore St. Augustine’s Shadier Side for Just $30

The Brothels & Booze: Exploring St. Augustine’s Red-Light District tour offers an intriguing look into the city’s hidden vice history. For $30 per person, this 1 hour 30 minutes guided walk takes you through West Augustine, around the famous Country Club area—once the epicenter of illegal liquor, gambling, and prostitution. The tour is perfect for those interested in the city’s less-legal past, with small groups limited to 25 travelers ensuring an intimate experience.

The tour departs from 218 W King St, a convenient location near public transportation, and features a mobile ticket for easy access. While the tour is brief, it covers several notable sites associated with St. Augustine’s clandestine activities, sharing stories that reveal how vice industries thrived alongside the city’s more wholesome image.

A key strength is the affordable price and the depth of historical detail from the guide, who is the author of Wicked St. Augustine. Keep in mind, the tour focuses on West Augustine’s darker past and involves walking, making it suitable for most physically able visitors. With good weather and a bit of curiosity, this tour offers a distinctive glimpse into the city’s underground history.

Key Points

• Price: $30 per person, with free cancellation up to 24 hours prior.
• Duration: About 1 hour 30 minutes, ideal for a quick but absorbing experience.
• Stops include several historic sites, such as Bog Brewing Company, Leo C. Chase & Associate’s Inc. Funeral Home, and Sweet City Cupcakes.
• Focus on West Augustine’s vice industry, including illegal liquor, gambling, and prostitution.
• The tour ends back at the meeting point, making it easy to continue exploring or return to your accommodations.
• Group size capped at 25 participants to maintain an engaging atmosphere.

Walking Through West Augustine’s Vice History

This tour is centered around the famous Country Club area, which historically catered to locals and visitors seeking illicit pleasures. The guide leads you through streets where illegal liquor was once served at places like Bog Brewing Company, now a local pub, but with a notorious past. You’ll learn how this hotel was part of the vice scene, and how it has transformed over time.

Visiting the Old Funeral Home’s Dark Past

One of the highlights is Leo C. Chase & Associate’s Inc. Funeral Home, which today operates as a thriving funeral business. In its former life, this building was the epicenter of St. Augustine’s vice industry, serving as the main location of the city’s most infamous madam. The guide shares stories of how this site was instrumental in the city’s underground activities for years.

Notorious Stops and Local Legends

Another stop, Sweet City Cupcakes, is included as part of the route, which underscores the darker history woven into everyday locations. While modern-day visitors can enjoy cupcakes here, the tour reveals its past ties to illicit activities. Each spot along the path has a story that connects it to the city’s hidden side, giving a layered perspective on how vice industries operated quietly in a city known for its charm.

Discovering the Roots of West Augustine’s Notorious Locations

The tour revisits Bog Brewing Company twice—once at the start and again at the end—highlighting its historical role in the vice economy. This local pub now offers libations where guests can unwind after the tour, providing a relaxed setting to reflect on the stories heard. The guide’s insights help piece together West Augustine’s reputation as a hub of clandestine activity.

Practical Details and Meeting Point

The tour starts at 218 W King St, a spot easily accessible by public transportation. It is designed for most travelers, with service animals allowed and weather considerations noted—if the weather turns poor, the experience may be canceled or rescheduled. The tour runs with a maximum of 25 participants, maintaining a manageable size for storytelling and questions.

Booking, Cancellation, and Flexibility

Booking is straightforward, with confirmation received within 48 hours, and most bookings are made 12 days in advance. The free cancellation policy allows for a full refund if canceled more than 24 hours before the start. This ensures flexibility for travelers with unpredictable schedules or weather concerns.

The Guide and Narrative Style

The tour is led by the author of Wicked St. Augustine, who shares detailed stories about the city’s vice history. The storytelling style is engaging and informative, providing context without sensationalism. The guide’s expertise ensures that even those unfamiliar with the city’s darker past will find the experience both illuminating and entertaining.

Who Should Consider This Tour

This walk is best suited for adults interested in history, true crime, or local legends. It’s an ideal way to explore the city’s underground side in a short timeframe, with a focus on West Augustine’s vice industry. The 1.5-hour duration makes it a manageable addition to a day full of sightseeing, especially for those with a curiosity about the city’s more clandestine stories.

Final Thoughts on Brothels & Booze in St. Augustine

The Brothels & Booze tour offers a unique lens into St. Augustine’s hidden past, combining storytelling with accessible walking routes. Its affordable price and focus on lesser-known sites make it a compelling option for travelers who want a different perspective on the city.

While it’s not exhaustive, the tour provides meaningful insights into the illegal side of St. Augustine’s history, highlighting how vice industries operated alongside the city’s more celebrated attractions. Visitors who are open to exploring the shadowy sides of history will find this tour both fascinating and well-presented.

Frequently Asked Questions

Is the tour suitable for children?
The tour is designed for adults, given its focus on sensitive topics like prostitution, illegal liquor, and gambling. Most travelers can participate, but it is best suited for mature audiences.

How long is the tour and what should I wear?
The tour lasts approximately 1 hour 30 minutes. Comfortable walking shoes are recommended, as the route involves outdoor walking through historic streets.

Can I cancel my booking?
Yes, the tour can be canceled up to 24 hours in advance for a full refund. Cancellations within 24 hours are not eligible for refunds.

Where does the tour start and end?
The tour begins and ends at 218 W King St, simplifying logistics for participants.

What’s included in the price?
The $30 fee covers the guided walk. There are no additional costs specified, and stops are free, with the option to enjoy drinks at the local pub after the tour.