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

If you’re curious about the less polished chapters of St. Augustine’s past, the Brothels & Booze tour offers an intriguing glimpse into the city’s underground side. This 1 hour 30-minute adventure, priced at $30 per person, is designed to reveal the stories behind some of West Augustine’s most notorious sites—places that once buzzed with illegal liquor, gambling, and prostitution. It’s a chance to see the city through a different lens, guided by an author who knows the dark corners—and the stories that linger there.

What we love about this experience is how it combines historical storytelling with tangible sites, making history come alive in a way that’s both educational and entertaining. Plus, the tour’s focus on authentic, lesser-known stories offers a refreshing change from the typical sightseeing fare. However, travelers should be aware that it’s a tour rooted in the city’s shady past, which might not be everyone’s cup of tea. It’s best suited for those with an interest in history, local lore, or the edgier side of tourist spots.

This tour provides a unique storytelling experience with accessible, walkable stops in the city’s historic West Augustine area. It’s ideal for curious travelers, history buffs, or anyone interested in the city’s more colorful past—just remember, it’s not a tame Victorian walking tour.

Key Points

• Authentic stories about St. Augustine’s vice industry, not sanitized history.
• Short, manageable itinerary makes it accessible and easy to fit into a day.
• Cultural insight into how illegal businesses served the local community historically.
• Affordable price point for a guided experience that offers plenty of storytelling.
• Small group setting (up to 25 travelers), fostering an intimate and engaging atmosphere.
• Free admission at stops means your ticket price mainly covers the guide’s storytelling.

An Entertaining & Informative Guided Walk

If you’re looking for a tour that’s more than just pretty streets and historical monuments, the Brothels & Booze tour offers an eye-opening peek into the shadowy side of St. Augustine’s past. It’s presented by Spyglass Tours, who have crafted a route that’s both educational and slightly provocative—perfect for those who enjoy uncovering the stories behind the stones.

The tour begins at 218 W King Street, the heart of the city’s historic West Augustine. From there, your guide takes you on a roughly 1.5-hour stroll through a neighborhood that once thrived on illegal activities. The group is limited to 25 participants, making it easy to ask questions and engage with the stories.

What makes this tour appealing is how it balances history with a sense of storytelling. Rather than just listing facts, the guide shares the stories of how these locations played roles in the city’s underground economy—ranging from illegal liquor to prostitution—with a focus on the lesser-known details. You’ll find stops at historical buildings that have since been repurposed, but which once held a very different function.

The Stops & Their Stories

Stop 1: Bog Brewing Company

Today, a lively local brewery and pub, but in the past, this was a site with a more clandestine reputation. Your guide will reveal the shadier history of this spot, shedding light on how alcohol prohibition and illegal taverns kept some businesses thriving. Expect a quick 15-minute stop with no admission fee, giving you a chance to picture the scene back in the day.

Stop 2: Leo C. Chase & Associate’s Inc. Funeral Home

This building today operates as a funeral home, but it has a notorious past as the main location of the city’s most infamous madam. The story here is about how vice industries operated discreetly in plain sight, providing essential services that many residents might have preferred to ignore. The guide shares anecdotes that highlight the complex relationship between legality and morality in historic St. Augustine.

Stop 3: Sweet City Cupcakes

While today a sweet treat for travelers, this stop hints at more infamous industries of the past. It’s a quick 15-minute visit, emphasizing how many familiar locations have layered histories—some darker than they appear. The guide connects the dots with stories of vice networks that intertwined with everyday life.

Stop 4: Return to Bog Brewing Company

Returning to the brewery, you’ll explore more of West Augustine’s notorious sites. The guide wraps up the tour with a summary of how these locations collectively contributed to the city’s underground economy. After the tour, you’re encouraged to stay and enjoy a drink at the brewery—an authentic way to reflect on what you’ve learned.

Practical Details

The tour is quite flexible. It begins at 218 W King St and ends back at the same spot, making it easy to combine with other sightseeing. It’s a mobile ticket, which means you just show up, and the guide takes care of the rest. The cost of $30 is reasonable considering the stories and the small-group intimacy. Plus, the stops are all free to enter, so your ticket mainly covers the guide’s storytelling expertise.

Because the tour is about 1.5 hours, it’s a manageable addition to a day of sightseeing. It’s near public transportation, making it accessible for most visitors. And since most travelers can participate, it’s suitable for a wide range of ages and interests—though discretion is advised for those sensitive to mature themes.

What We Think

The Brothels & Booze tour does a good job of offering a different perspective on St. Augustine. It’s a bit edgier than the usual historic walk, making it appealing if you’re curious about the city’s less sanitized stories. The stories are well presented, and the stop locations are thoughtfully chosen to maximize storytelling potential.

One note of caution: this isn’t a tour for those seeking family-friendly or light-hearted history. It’s focused on the more illicit side of the city’s past, which some might find a bit gritty or uncomfortable. Still, for those interested in authentic, behind-the-scenes stories, it delivers a fascinating look.

Guests have appreciated the expert storytelling and the small-group atmosphere. Some mention that the stories are “shady but interesting,” and it’s a good way to learn about how vice industries operated discreetly in a city that also boasts beautiful beaches and historic charm.

The Sum Up

The Brothels & Booze tour offers a sharply focused look at a lesser-known facet of St. Augustine. It’s perfect for travelers who want to go beyond the usual tourist stops and understand how the city’s underground economy shaped its development. The tour’s storytelling style makes history engaging and memorable, especially when walking through the very streets where these stories unfolded.

While it may not suit everyone—particularly those uncomfortable with mature themes—those with a taste for edgy history, local lore, or stories of vice and clandestine activities will find this tour compelling. It’s a fun, informative, and surprisingly balanced account of a side of St. Augustine that’s often overlooked but undeniably fascinating.

For anyone who enjoys uncovering the city’s secrets and appreciates a good story, this tour is a worthwhile addition to your visit. Just remember to keep an open mind and enjoy the tales behind the city’s more shadowy past.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately 1 hour 30 minutes, making it a short but rich experience that fits easily into your day.

What is the starting point?
It begins at 218 W King Street in St. Augustine, which is conveniently located in West Augustine.

Is there an admission fee for the stops?
Most stops are free to enter, so your ticket primarily covers the guide’s storytelling. The stops include places like the Bog Brewing Company and Leo C. Chase & Associate’s Inc.

Can I cancel the tour?
Yes, you can cancel for a full refund if you do so at least 24 hours in advance. Cancellations within 24 hours are not refunded.

Is the tour suitable for children?
Most travelers can participate, but given the mature themes of vice and illegal activities, it’s best for older teens and adults.

Is the tour accessible via public transportation?
Yes, it’s near public transit options, making it easy to reach the starting point.

What should I wear?
Comfortable walking shoes are recommended as it’s a walking tour through historic streets.

Does the tour have a group size limit?
Yes, it’s capped at 25 travelers, fostering an intimate atmosphere and more personalized storytelling.

Will I receive a mobile ticket?
Yes, it’s a mobile ticket, so you simply show it on your phone at the start location.

This tour is a neat way to add a bit of intrigue to your trip, revealing how the city’s past still echoes in its streets today. Whether you’re a history enthusiast or a curious traveler, the Brothels & Booze tour offers a memorable peek behind the curtain of St. Augustine’s more colorful history.