Secret St. Augustine Historic Walking Tour

If you’re visiting St. Augustine and craving a tour that’s both entertaining and packed with local stories, the Secret St. Augustine Historic Walking Tour might be just what you’re looking for. Offered by Naughty History Tours, this journey promises a playful peek into the city’s less-known tales—think naughty behaviors, secret histories, and colorful characters—alongside practical insights and a healthy dose of fun.

What we love about this experience is the way it combines authentic storytelling with some well-placed humor, making history feel lively rather than stuffy. Plus, the tour’s ending at a cozy wine bar adds a relaxed, social vibe that’s perfect after a walk through the old streets. A possible downside? Since it’s a relatively short and casual walk, those expecting a comprehensive deep dive into every corner of St. Augustine might find it a bit light on detail. Still, for those who appreciate lively stories and local color, this tour fits like a glove. It’s especially well-suited for travelers who enjoy a blend of history, humor, and a touch of naughtiness with their sightseeing.

Key Points

Engaging storytelling makes history come alive with a humorous twist.
Short, walkable route means no long hikes—ideal for relaxed exploration.
Ending at a wine bar offers a social, laid-back finish.
Rich local tales include stories of prohibition, bootlegging, and colorful characters.
Affordable price point provides good value for a lively experience.
Private tour option ensures a more personalized experience.

What to Expect from the Secret St. Augustine Historic Walking Tour

This 90-minute stroll through the streets of St. Augustine is designed for those who want a taste of local secrets and quirky stories, all served with a generous side of humor. Starting at the BART art and wine bar, the tour kicks off with the history of the Fatio House, a rare boarding house notable for its women ownership spanning over 200 years—no scandal here, just a fascinating glimpse into early female business owners.

The First Stop: The Historic Plaza and Fatio House

Our guide, Sebastian, begins by pointing out the monument to Spain’s failed constitution—a reminder of the city’s complex political past. He shares stories about the city’s churches, civil rights milestones, and the influence of Flagler, the railroad magnate who helped shape modern St. Augustine. It’s a good mix of the well-known and the less-glamorous, giving newcomers a solid grounding while teasing out local secrets.

The Gilded Age and the Robber Barons

Next, we enter the Gilded Age, a period of dazzling wealth and ostentatious mansions. Sebastian narrates tales of the so-called “Newport of the South”, a nickname for St. Augustine during this era, highlighting the over-the-top lifestyles of the era’s robber barons. He’s cheeky about their “naughty behaviors,” which might include everything from scandalous parties to shady dealings—stories that spice up the history and make it more memorable.

The Zorayda House and Prohibition Naughtiness

One of the tour’s highlights is the story of the Zorayda House, a Moorish Revival mansion that’s often called the city’s most famous historic home. Sebastian shares the inside scoop on the naughty deeds during Prohibition, when St. Augustine became a hub for bootleggers. The tales of secret tunnels, hidden speakeasies, and illicit activity add a fun, rebellious layer to the town’s story.

Contrasts and Local Characters

A particularly charming part of the walk involves a story about a notable inhabitant of the Zorayda House—someone whose life was quite different from the city’s raucous Prohibition scene. It’s a reminder that behind every historic building, there’s a personal story, often more relatable than the grand facades.

From Opium Dens to Local Victories

Before wrapping up, Sebastian takes us to two stops: one about a dentist-turned-taxidermist, and another about opium dens, casinos, and the conflicts between locals and the robber barons. Interestingly, the locals “won” this battle, maintaining their community’s charm and resisting the overreach of wealthy outsiders—an inspiring tale of local resilience.

The Final Stop: Aviles Street and the Connection to Juneteenth

We end back on Aviles Street, the oldest street in St. Augustine, with an explanation of its link to Juneteenth and a mysterious story that leaves you pondering. Before the walk finishes at the wine bar, Sebastian shares a few more local insights, ensuring you leave with a sense of the city’s layered history.

Practical Details and Experience Quality

The tour is priced at $37 per person, which is quite reasonable given the storytelling quality and the intimate nature of the private tour. Booking about 123 days in advance suggests good demand, and the mobile ticket system makes it easy to join. The one-and-a-half-hour duration makes it an ideal quick but meaningful experience, especially for those on a tight schedule or seeking a relaxed, social way to explore.

The tour begins at 11d Aviles Street, right in the heart of the historic district, and ends conveniently back at the starting point. Since it’s a private tour, your group will enjoy a more personalized experience, with Sebastian tailoring stories and tips based on your interests. The guide’s humor and local insights make the history accessible and fun, especially for first-time visitors or those looking for a different perspective beyond the usual tourist spots.

The Value of the Experience

For just $37, you get not only a lively overview of St. Augustine’s darker, more colorful past but also tips from a local guide who clearly loves sharing stories. The ending at a wine bar means you can unwind and discuss the tales with your group, making the experience feel more like a social outing than a typical tour.

Accessibility and Considerations

Most travelers can participate, and service animals are allowed, making it accessible for different needs. Since it’s an outdoor walking tour, good weather enhances the experience, and cancellations are flexible up to 24 hours in advance.

Who Will Love This Tour?

If you’re looking for a light-hearted, story-rich exploration that reveals St. Augustine’s less polished side, this tour is perfect. History buffs who enjoy hearing about naughty deeds, local characters, and bootlegging stories will find it especially engaging. It’s also ideal for travelers who want a relaxed, informal experience that combines history with humor, topped off with a glass of wine. Families with older children or adults traveling together will appreciate the engaging storytelling, while those seeking a more serious or comprehensive tour might want to supplement this experience with additional excursions.

The Sum Up

The Secret St. Augustine Historic Walking Tour offers a delightful, humorous perspective on the city’s past, blending local legends, colorful characters, and tales of naughty behavior. Its casual pace and private format make it a perfect choice for visitors who want an entertaining yet insightful glimpse into the city’s more mischievous side.

For those eager to learn about St. Augustine beyond the usual tourist spots, this tour adds personality and fun to your visit. The ending at a wine bar makes it especially appealing for travelers who enjoy socializing and relaxing after a walk. It’s a fantastic way to connect with local stories, all while feeling like you’re sharing secrets with a knowledgeable friend.

If you value storytelling that’s both informative and amusing, and love the idea of uncovering the city’s hidden tales, this tour is a worthwhile addition to your St. Augustine itinerary.

FAQ

How long is the tour?
The tour lasts approximately 1 hour and 30 minutes, making it a manageable and relaxed experience.

Where does the tour start and end?
It begins at 11d Aviles Street and ends back at the same location, right in the historic district.

Is this tour suitable for children?
Most travelers can participate, but since it includes stories of naughty behavior and adult themes, it’s best for older children and adults.

Do I need to book in advance?
Yes, the tour is usually booked around 123 days in advance, and a mobile ticket simplifies the process.

What is the price?
The tour costs $37 per person—considering the storytelling, private format, and ending at a wine bar, it offers good value.

Is there a cancellation policy?
Yes, you can cancel free of charge up to 24 hours before the tour, with full refunds.

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

What are the features of the tour?
It’s a private walking experience with an engaging guide, sharing stories about St. Augustine’s naughty past, notable buildings, and local heroes.

Do I need to worry about the weather?
Yes, since it’s an outdoor tour, good weather enhances the experience. Poor weather may lead to rescheduling or refunds.

Are there other similar experiences?
Yes, similar tours include hop-on-hop-off trolley rides, sunset sails, boat rides, and ghost tours—more traditional or themed options, but this one stands out for its humorous and naughty stories.

In all, the Secret St. Augustine Historic Walking Tour offers a memorable, fun way to see the city’s lesser-known side. Whether you’re a history enthusiast or just looking for a good laugh amid beautiful surroundings, this tour delivers personality, charm, and some eye-opening stories worth sharing.