Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Key Points

• Affordable and Engaging: Priced at $30 per person, this 1 hour 30 minutes tour offers a fascinating glimpse into the city’s seedy past.
• Expert Guide: Ann Colby, the storyteller behind the tour, is known for her extensive research and passionate storytelling.
• Unique Focus: The tour highlights illegal private clubs, speakeasies, brothels, and underground gambling spots that shaped St. Augustine’s history.
• Convenient Stops: The journey includes visits to iconic locations like the Lightner Museum, Flagler College, and St. George Street.
• Nighttime Experience: Starting at 8:00 pm, the tour offers a different perspective of the city’s hidden history after dark.
• Highly Rated: With a 5.0 rating from 86 reviews and 97% recommendation, this tour is praised for its entertaining and informative approach.

The Dark Side of St. Augustine Begins at Lightner Museum

The tour kicks off at the Lightner Museum, with a quick 10-minute stop in front of the historic Alcazar Hotel, now housing the museum. The courtyard provides a visual connection to the city’s past, with sights of the Ponce de Leon Hotel—a symbol of the Gilded Age luxury.

From here, the guide leads guests to Flagler College, the reincarnation of Henry Flagler’s opulent Ponce de Leon Hotel. This 10-minute stop offers insights into the decadence of the era and the contrast with the city’s hidden, illicit activities.

Exploring St. George Street’s Secret Tales

A key highlight is a walk along St. George Street, where stories of private clubs, gambling halls, speakeasies, and boarding houses unfold. These establishments served both vacationers and local working-class residents, forming the backbone of the city’s underground economy.

Guests learn that many boarding houses doubled as brothels, a common practice that helped sustain the city’s lively nightlife during Prohibition. The guide shares details about how these hidden venues operated discreetly amid the city’s picturesque façade.

Plaza de la Constitucion and Its Shadowed History

The tour’s next stop is Plaza de la Constitucion, where discussions focus on the gambling halls, speakeasies, and brothels that thrived in secret. The guide reveals how these venues were often concealed behind seemingly innocent fronts, allowing illicit activities to flourish undetected.

This area offers a compelling look at how St. Augustine managed to sustain its seedy underbelly despite the city’s reputation for historic charm. The stories shed light on the political powers that tolerated or turned a blind eye to this underground scene.

The Experience of a Nighttime Tour in Historic St. Augustine

The tour starts at 8:00 pm, and while it involves a few short walks totaling only a handful of blocks, most of the experience is sitting down, listening to stories. The group size is limited to 26, which allows for an engaging, personalized experience.

Guests should note that the tour often lasts longer than the advertised 1.5 hours, sometimes extending to nearly 3 hours. The guide, Ann, does a great job of sharing as much detail as guests want and is known for her entertaining storytelling.

The Guide: Ann Colby’s Passion and Knowledge

Ann Colby is the force behind this tour. She’s written a book on the subject and spends years researching the shadowy side of St. Augustine. Attendees praise her for her enthusiasm, thorough knowledge, and storytelling skills.

Her passion for revealing lesser-known history shines through, making the tour not only informative but also highly engaging. Guests note that she is considerate of their pace, often extending the tour if asked and making everyone feel comfortable.

Logistics and Accessibility

Starting point is at the Lightner Museum, located at 75 King St, St. Augustine. The tour is near public transportation, and service animals are allowed. The tour is designed to accommodate most travelers, with manageable walking and sitting, making it accessible for many.

Guests should be prepared for outdoor walking in the evening, and bringing a lightweight blanket is recommended if it’s chilly. The tour ends back at the starting point, ensuring easy access to accommodations or other city attractions.

Why This Tour Stands Out Among Others

Unlike typical historic walks, this tour offers a focused look into the underground life of St. Augustine. It emphasizes secret venues, illegal activities, and discreet lifestyles that shaped the city’s less celebrated history.

The small group size and personal storytelling make it a compelling choice for those who already know the traditional history of St. Augustine and crave a different perspective. The cost-effective price and high ratings make it a worthwhile addition to any evening itinerary.

Limitations and Considerations

While the tour provides fascinating insights, it is not a walking tour of historic houses or a ghost tour, nor does it include alcohol tasting or child-friendly activities. The focus is on informative stories about illicit activities, so those seeking ghost stories or family-friendly options may need to look elsewhere.

Guests should also note that the tour runs longer than 1.5 hours at times, so flexibility is advised when planning evening activities afterward.

Final Thoughts on Wicked St. Augustine: Bootleggers, Brothels & Gambling

This tour offers a unique look into the city’s hidden past, driven by Ann Colby’s extensive research and storytelling talent. It appeals most to those interested in lesser-known historical details, especially relating to Prohibition, underground gambling, and vice industries.

At just $30, the experience is well worth the price for its depth and entertainment value. The evening timing provides a different atmosphere, enhancing the intrigue of discovering St. Augustine’s shadowy side after sunset.

While it’s not suitable for children or those seeking a leisurely walk through historic sites, it’s perfect for adults craving a lively, informative exploration of the city’s darker chapters. If you enjoy stories of the underbelly of history, this tour is a must-try during your visit.

Frequently Asked Questions

How long is the tour?
The tour is advertised as 1 hour 30 minutes, but it often lasts closer to 3 hours depending on the group’s interest and pace.

Where does the tour start?
It begins at the Lightner Museum at 75 King St, St. Augustine.

What is included in the tour?
The tour covers stories about underground gambling, speakeasies, brothels, and illicit activities tied to the city’s history.

Is the tour suitable for kids?
No, this tour is not child-friendly as it focuses on adult themes like vice industries and illegal activities.

What should I bring?
A lightweight blanket is recommended if it’s chilly. The tour involves mostly sitting with short walks.

Can I cancel if I change my mind?
Yes, free cancellation is available up to 24 hours before the start, with full refunds.

Is the tour accessible?
Yes, it is near public transportation and designed to accommodate most travelers, with manageable walking and sitting.

What makes this tour stand out?
The expert storytelling of Ann Colby and the focus on St. Augustine’s hidden vice scene set this experience apart from standard historical tours.

Are there any other similar experiences?
Yes, options like Ghosts and Gravestones, Dolphin and Wildlife Adventures, or Hop-On Hop-Off Trolley tours are available, but none focus specifically on the underbelly of history like this one.

Is the tour suitable for first-time visitors?
Absolutely, especially for those already familiar with traditional city sights and eager to explore lesser-known stories.

How do reviews rate this tour?
It holds a perfect 5.0 rating from 86 reviews, with 97% recommending it, highlighting its entertaining storytelling and depth of knowledge.