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

Traveling to St. Augustine? If you’re already familiar with the main sights and want a different perspective, this nighttime tour offers a fascinating look into the city’s less polished past. Taught by a passionate guide, it shines a light on the “shadowy” side of the town—covering everything from illegal gambling dens to secret brothels—revealing a side of St. Augustine most visitors never hear about.

What we love about this experience is its focus on less conventional stories that add depth to your understanding of the city. Plus, the guide’s storytelling skills make even the darkest chapters engaging and memorable. The second thing that stands out is the value for money—at just $30, the tour is packed with stories and insights that go beyond standard city sightseeing.

One thing to keep in mind is the duration—reviews mention it often extends well beyond the advertised 1.5 hours, which can be a good or bad thing depending on your schedule. It’s also a seated, mostly stationary experience—so if you’re expecting lots of walking, this might not be the best fit. It’s particularly suited for those who love history with a twist, especially if you’re already familiar with the city’s more traditional stories.

If you’re into uncovering secret histories or simply want to see another side of St. Augustine, this tour could be a perfect addition to your trip. It’s especially great for history buffs, or anyone intrigued by the city’s more clandestine past.

Key Points

• Focus on the “dark” side of St. Augustine’s history including illegal activities and underground culture.
• Engaging storytelling from a knowledgeable guide, Ann, who has written about this hidden history.
• Mostly seated with brief stops, making it accessible for those who prefer less walking.
• Cost-effective at $30 per person with highly positive reviews.
• Extended length—often longer than the advertised 1.5 hours—so be prepared for a longer experience.
• Great for history lovers who want stories they won’t find in typical tours.

A Closer Look at the Itinerary

Start at the Lightner Museum

The tour kicks off outside the historic Lightner Museum, located in the courtyard of the old Alcazar Hotel, which itself is a sight. This spot sets the tone for the evening, as you get a quick look at the grandeur of St. Augustine’s past. The museum itself is free to view from the outside, making it an easy starting point. Expect to spend about 10 minutes here, soaking in the ambiance and hearing some initial stories.

Flagler College’s Historic Tour

Next, you’ll stroll past the former Ponce de Leon Hotel, built by Henry Flagler. This was once the height of luxury during the Gilded Age. While the tour doesn’t involve entering the college, you’ll hear plenty of stories about the decadence that once thrived here. It’s a chance to understand how the city’s elite played a role in its darker past.

St. George Street

The core of the tour takes you down St. George Street, the city’s main thoroughfare. Here, the guide shares tales of private clubs, gambling halls, speakeasies, and boarding houses—many of which doubled as brothels in their day. As one reviewer notes, “You will learn so much! Ann is very entertaining,” giving a lively feel to these stories. You’ll see the spots that once hosted illicit activities—though the buildings may still stand, they now serve different purposes.

Plaza de la Constitución

The final stop is at this historic square, where stories continue about underground gambling, secret bars, and hidden rooms. It’s a fitting ending point as stories of clandestine activities unfold, revealing how the city managed to keep its darker side alive despite the law.

What to Expect During the Tour

Length and Pace

Most reviews mention the tour lasts longer than the official 1.5 hours—some say it’s closer to 3 hours. Ann, the guide, is so passionate that she tends to share plenty of details, which can extend the experience. This is a good thing if you love stories but worth noting if your schedule is tight.

Group Size and Comfort

The tour is capped at 26 travelers, ensuring a personal touch. Since most of it involves sitting and listening, it’s suitable for older travelers or those who prefer a relaxed pace. Be aware that the tour involves some standing and brief walks, but overall, it’s quite manageable.

Cost and Value

At $30 per person, this tour offers excellent value considering how much detailed information you get. Many reviewers highlight how unique and “mind blowing” the stories are, especially since Ann cites her sources and clearly loves sharing her knowledge. You get a good balance of entertainment and education, with a focus on stories that are often overlooked.

Accessibility and Suitability

While not explicitly marketed as family-friendly, the seated nature and PG-13 content make it suitable for most adults and older kids interested in history. It’s not a ghost tour or a pub crawl, so don’t expect drunken tales or supernatural stories—this is all about real, if some-what seedy, history.

What We Appreciate About the Experience

Knowledgeable Guide

Ann, the guide, is a treasure trove of information. She not only shares stories but also references her own book on the subject, adding credibility. Reviewers mention her storytelling prowess—she keeps everyone engaged and eager for more.

Authentic Stories

The stories of brothels, gambling, and clandestine activities are told openly, providing a different angle on the city’s history. It’s a perspective you won’t get from traditional tours, making it especially appealing if you’re into the more mysterious side of history.

Excellent Value

Considering the price, the depth of stories and the tourist-friendly approach make this tour stand out. Reviewers describe it as “very informative and fun,” with some stating it was the best tour they took while visiting.

Unique Perspective

Many reviews emphasize how Ann’s storytelling offers insights into characters and events that are rarely discussed, giving a fuller picture of St. Augustine’s past. The tour also touches on significant personalities like Flagler, providing a comprehensive yet lively narrative.

Potential Drawbacks to Keep in Mind

Longer Than Expected

The tour often exceeds the advertised time—expect closer to 3 hours if you’re attentive and engaged. While most reviews praise this, travelers on tight schedules should plan accordingly.

Limited Walking

It’s primarily a seated, sit-and-listen experience, which might disappoint those expecting a more active exploration. It’s best suited for those who prefer stories over extensive walking.

Weather Dependence

Since most of the tour is outdoors, bad weather could impact the experience. The tour provider states that poor weather may lead to cancellation or rescheduling.

Not Suitable for Children

While not explicitly labeled as family-friendly, the content is geared toward adults interested in the city’s darker history. Some stories involve illicit activities, so it’s better suited for older teens and adults.

Final Thoughts

This Wicked St. Augustine tour offers a fascinating glimpse into the city’s less glamorous past, told through the lens of engaging storytelling by Ann. It’s perfect for history buffs who crave stories that aren’t in the guidebooks and for travelers looking for a different way to experience St. Augustine after dark.

The tour’s combination of knowledge, storytelling, and value makes it a standout choice for those interested in the city’s clandestine history. It’s especially appealing if you’re comfortable with the idea of a longer, seated experience and have already seen the main sights.

Overall, this tour is a solid pick for anyone wanting to add depth and a dash of the mysterious to their trip—just go prepared for a longer evening and a few told tales that might surprise you.

Frequently Asked Questions

How long does the tour usually last?
Most reviews mention it often extends beyond the advertised 1.5 hours, sometimes nearing 3 hours, depending on how much the guide shares.

Is the tour suitable for children?
It’s best suited for adults or older teens, as it covers topics like brothels and illegal gambling that aren’t child-friendly. It’s mainly a storytelling experience focused on the city’s darker past.

What’s included in the price?
You simply pay $30 per person for the guided storytelling. The tour doesn’t include entry into any museums or sites, just a walk around key locations with stories told from the outside.

Can I cancel if my plans change?
Yes, the tour offers free cancellation up to 24 hours before the start time, with a full refund.

Is it a walking tour?
It’s mostly a seated experience with brief walks between stops. Most of the time is spent sitting and listening.

How big are the groups?
The maximum group size is 26 travelers, ensuring a more personal and engaging experience.

What should I wear or bring?
Since most of the tour is outdoors, dress for the weather. Reviewers suggest bringing a lightweight blanket if it’s chilly.

Does the tour operate rain or shine?
It requires good weather. If canceled due to poor weather, you’ll be offered a different date or a full refund.

Who runs this tour?
It’s provided by Spyglass Tours, and Ann is the guide who makes it special with her detailed stories and passion for the subject.

If you’re curious about the hidden stories of St. Augustine’s past, this tour is a compelling way to experience a different side of the city—just be ready for a longer, seated immersion into its more clandestine history.