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

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
Rating: 5.0/5 (86 reviews)
Location: St. Augustine, USA
Price: $30.00 per person
Duration: About 1 hour 30 minutes
Features: Mobile ticket

A quick look at the experience
This tour is a fascinating journey into the less glamorous side of St. Augustine’s storied past. For just $30, you’ll spend around an hour and a half walking through some of the most historic streets of the city, led by guides like Ann, who are passionate and well-informed. You’ll visit iconic sights like Lightner Museum, Flagler College, and St. George Street, but what sets this experience apart are the stories about illegal gambling dens, speakeasies, and brothels that once thrived behind the city’s charming facades.

Two things we love about this tour: First, the depth of local knowledge Ann shares, which makes history feel alive and full of surprises. Second, the ease of the sit-and-listen format, with most of the walk spent sitting at key spots, making it accessible for all ages and energy levels.

One thing to keep in mind is that the tour often runs longer than the advertised 1.5 hours—some reviews mention it extending to three hours—so plan accordingly if you’re on a tight schedule.

This experience suits history buffs, curious travelers eager to learn about the city’s hidden and darker stories, or anyone interested in a more colorful version of St. Augustine’s past. It’s especially great if you’ve already explored the usual sights and want a different perspective.

Key Points

• In-Depth Local Stories: Guides like Ann bring the city’s seedy history to life with detailed tales.
• Accessible Format: Mostly sitting and short walks, making it suitable for a wide range of travelers.
• Authentic Content: Focus on bootlegging, brothels, gambling, and underground activities, often left out of traditional tours.
• Historical Landmarks: Pass by notable sites like Flagler College and Lightner Museum, with stories intertwined.
• Flexible Length: Tour can go longer than 1.5 hours; be prepared for an immersive experience.
• Value for Money: At $30, it’s a niche tour that offers more than just surface history, with many reviews praising its depth.

A Deep Dive into the Tour Experience

Starting at the Lightner Museum

Your journey kicks off at the Lightner Museum in the courtyard in front of what was once the Alcazar Hotel. This spot is not just a photo op but a gateway to stories of secret clubs and underground activities, with views of the nearby Ponce de Leon Hotel, now Flagler College. It’s a great starting point because it situates you right among the city’s historic architecture, setting the stage for the tales ahead.

Exploring Flagler College

Next, you’ll pass by the former Ponce de Leon Hotel, built by Henry Flagler during the Gilded Age. While most tours focus on the opulence, on this tour, Ann highlights the dark side—stories about covert gambling halls and illicit nightlife that operated beneath the grandeur. The 10-minute stop here allows you to absorb the contrasting stories of luxury and vice, enriching your understanding of how the city’s fortunes were intertwined with its underground economy.

Walking down St. George Street

The tour then winds down St. George Street, the bustling heart of the city’s commerce and nightlife in days past. Here, Ann shares how the private clubs and speakeasies dotted the streets, serving both vacationers and locals seeking entertainment away from the law. The stories woven into the brick facades reveal a city that thrived despite prohibition, with many boarding houses doubling as brothels—a fact many visitors find eye-opening.

Pass by the Plaza de la Constitución

Your final stop is at Plaza de la Constitución, where Ann narrates tales of gambling halls and clandestine bars. The stories of prohibition-era speakeasies and illegal gambling are often the highlight for visitors, offering a glimpse into the city’s ‘hidden’ side that people rarely see. During this segment, the guide’s storytelling style—informative yet entertaining—keeps everyone captivated.

Authenticity, Value, and Practical Tips

This tour is all about storytelling that connects history with real places. It’s not a walking marathon but a sit-and-listen style that makes the experience comfortable and engaging. Reviews consistently mention the knowledgeable guides, especially Ann, who has written extensively on the dark side of St. Augustine’s history. She’s praised for her storytelling skills and her ability to share stories backed by research.

The tour’s price, $30, is quite reasonable considering the depth of stories and the insider knowledge you gain. If you’re someone who appreciates authentic, lesser-known stories over tourist clichés, you’ll find this tour to be a valuable addition to your visit.

One key consideration: because the tour often extends beyond the expected 90 minutes, it’s wise to reserve some extra time afterward. Also, since most of the activity is sitting with occasional short walks, it’s accessible for most travelers, but be prepared for an immersive, sometimes lengthy storytelling session.

Group Size and Logistics

With a maximum of 26 travelers, the group remains intimate enough for personalized stories, yet large enough to create a lively atmosphere. The meeting point is at the Lightner Museum, with tours starting at 8:00 pm—a perfect time to experience the city’s evening ambiance and perhaps reflect on the stories under the soft glow of historic streetlights.

Who Will Love This Tour?

This experience is best suited for history enthusiasts who crave stories beyond the typical tourist narrative. If you’re interested in the city’s underbelly—bootlegging, brothels, and speakeasies—this tour will satisfy your curiosity. It’s also ideal for story lovers who appreciate engaging guides and authentic details backed by research.

While it’s not a tour for those seeking a physical workout or ghostly hauntings, it’s perfect for travelers who want an entertaining, educational, and somewhat provocative look into what really went on behind the scenes of St. Augustine’s glamorous image.

The Sum Up

In short, Wicked St. Augustine offers a unique glimpse into the city’s darker past, revealing stories that most visitors miss. For $30, you get a well-researched, engaging storytelling experience led by passionate guides like Ann. The focus on underground activities, brothels, and gambling adds a layer of intrigue that brings history to life in a very tangible way.

This tour is an excellent choice for history buffs, curious explorers, and those wanting a different perspective on St. Augustine’s past. It combines authentic storytelling with accessible, sit-down comfort—making it a memorable, worthwhile addition to your trip. If you’re ready to hear tales not found in guidebooks and enjoy a relaxed, engaging walk through the city’s shadowy corners, this tour won’t disappoint.

FAQ

Is this tour suitable for children?
This tour is focused on the darker, more adult-themed aspects of history, such as brothels and illegal gambling. It is not child-friendly.

How long does the tour usually last?
It’s advertised as about 1 hour 30 minutes, but many reviews mention it can extend up to three hours if the guide shares more stories.

What’s the meeting point?
The tour starts at the Lightner Museum, 75 King St, St. Augustine, FL.

Is the tour walkable?
Most of the tour involves sitting at key points, with only a few short walks, making it accessible for most travelers.

What’s the price?
$30 per person, which offers good value considering the depth of the stories and the guide’s expertise.

Are service animals allowed?
Yes, service animals are permitted on the tour.

Is this tour suitable for people with mobility issues?
Since most of the experience is sitting and only short walks are involved, it’s generally suitable for those with limited mobility.

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

What should I bring?
A light jacket or blanket if it’s chilly, as most of the tour is seated outdoors.

Will I learn about the city’s traditional history?
This tour focuses on the lesser-known, darker stories rather than the typical colonial or Gilded Age history.

Overall, Wicked St. Augustine provides a compelling alternative perspective on this historic city. Its combination of authentic storytelling, fascinating tales of illicit activities, and accessible format makes it a standout experience for those eager to see a different side of St. Augustine.