Secret St. Augustine Historic Walking Tour

Exploring the Secret St. Augustine Historic Walking Tour: A Fun and Authentic Journey Through Time

If you’re looking for a way to see what makes St. Augustine truly unique, this Secret St. Augustine Historic Walking Tour offers a lively, insider look at the city’s lesser-known stories. Designed for those who enjoy a mix of humor, history, and a dash of mischief, this 90-minute tour promises a fun way to get to know the city’s colorful past. Unlike typical historical walks, it combines storytelling with relaxed stops, all topped off with a glass of wine — or two.

Two things we especially appreciate about this experience are its focus on local stories that often go unnoticed and the fact that it begins and ends at a cozy wine bar, giving a hint of the naughty side of town. The tour’s intimate, private setting means you’re not just a face in a crowd, and Sebastian, the guide, is known for sharing stories that range from the amusing to the downright scandalous. One possible consideration is the limited duration — if you’re a history buff or want a deep dive, this might serve better as a fun appetizer than a comprehensive history lesson.

This experience is perfect for travelers who love stories with a bit of spice, enjoy walking at a leisurely pace, and want to combine history with local flavor. It’s especially suited for those who appreciate a relaxed, humorous approach to discovering the city’s hidden tales.

Key Points

• Authentic storytelling: The tour shares stories you won’t find in regular guidebooks, from prohibition-era bootlegging to local legends.
• Convenient start/end points: Begins and ends at a local wine bar, making it easy to relax and socialize.
• Private experience: Only your group participates, ensuring a personalized and engaging time.
• Affordable value: At $37 per person, it offers a quick yet vivid peek into St. Augustine’s more mischievous side.
• Knowledgeable guide: Sebastian’s storytelling style adds humor and authenticity, making history lively and fun.
• Unique stops: From historic houses to old civil rights sites, each stop offers a glimpse into the city’s layered past.

In-Depth Look at the Experience

Starting at the BART Art and Wine Bar

Our journey kicks off at 11 Avenida Street, where the vibe is relaxed and inviting. The tour begins inside the wine bar, setting the tone for a leisurely, enjoyable stroll. Here, Sebastian introduces the group to the Fatio House, a rare example of a boarding house that has avoided the common pitfalls of the time, notably avoiding prostitution. The fact that it was women-owned for over 200 years makes it a noteworthy piece of local history, and Sebastian’s anecdotes make it come alive.

Exploring the Historic Plaza and Monuments

Next, we wander into the vibrant Historic Plaza, where Sebastian points out the monument to Spain’s failed constitution — a reminder of the city’s complex political past. As we stroll, he shares stories about the churches, civil rights, and the influential figure of Flagler, Florida’s railroad magnate who played a critical role in shaping the city. The stories here give insight into how St. Augustine balanced its colonial roots and modern development.

The Gilded Age and the Robber Barons

A highlight of the tour is the peek into the Gilded Age, when St. Augustine was nicknamed the “Newport of the South”. Sebastian describes the wealth and decadence of the robber barons and their often naughty behaviors. We hear about the naughty antics of the era’s elite, which adds a playful touch to this historic period. Expect vivid tales of extravagance, corruption, and a few secrets that hint at the city’s more scandalous past.

The Zorayda House and Prohibition-Era Tales

One of the most captivating stops is the Zorayda House, a historic mansion whose story is intertwined with the city’s prohibition days, when St. Augustine was a hub for bootleggers. Sebastian points out the “naughty” side of the house’s history, contrasting it with tales of the residents’ innocence. It’s a vivid reminder that even in the most elegant settings, mischief was often afoot.

Contrasts and Local Characters

Sebastian shares a charming story about a resident of the Zorayda House, providing a human face to the historic narrative. The contrast between the genteel exterior and the naughtiness behind closed doors makes the city’s history more relatable and fun.

Hidden Stories of Crime and Resistance

Two stops near the end of the tour explore some of the city’s darker secrets — from a dentist turned taxidermist to stories of opium dens and casinos, illustrating the colorful conflict between the locals and the robber barons. Sebastian recounts how, despite the wealth and influence of the elite, the local community managed to win some battles, preserving their own way of life.

The Final Stop and Connection to Juneteenth

We finish back on Aviles Street, the oldest street in the city, known for its lively shops and vibrant history. Here, Sebastian explains the connection between the city’s history and Juneteenth, along with a mysterious story that adds a layer of intrigue. Before leaving, many find themselves intrigued enough to explore more of the neighborhood’s hidden corners.

Practical Details and What to Expect

Duration, Price, and Group Size

This tour lasts approximately 1 hour 30 minutes, making it perfect for a relaxed afternoon. At $37 per person, it’s quite reasonable given the personalized storytelling and the inclusion of a wine bar experience. Because it’s a private tour, only your group will participate, ensuring an intimate and flexible experience.

Meeting Point and End Location

The tour starts at 11 Avenida Street and wraps up at the same spot. The convenience of starting and ending at the same location means you can easily plan a post-tour drink or meal.

Accessibility and Weather

The walk is described as easy, suitable for most travelers with reasonable mobility. Since the tour is outdoors, good weather is important; if canceled due to rain, you’ll be offered a different date or a full refund. Service animals are allowed, ensuring accessibility for travelers with pets or assistance needs.

Booking and Cancellation

Booking in advance is recommended — on average, trips are booked 123 days ahead. Cancellation policies are straightforward, offering full refunds if canceled at least 24 hours in advance.

Authentic Insights from Others

Though the tour currently has no reviews, the description hints at a lively, humorous style that many find appealing. The emphasis on local tips, history with a naughty twist, and a wine bar start/end sets this apart from more traditional, dry historical walks.

Overall Value and Who It’s For

This walk is a delightful choice for those wanting an entertaining, quick taste of St. Augustine’s lesser-known stories. With its focus on scandal, humor, and local secrets, it appeals especially to travelers who enjoy stories that spice up history. The inclusion of a wine bar makes it perfect for a relaxed afternoon, especially after a morning of sightseeing.

While it doesn’t replace in-depth history tours, it offers an engaging, authentic experience that’s perfect for couple outings, small groups, or anyone looking to add a bit of mischief to their visit.

Final Thoughts

The Secret St. Augustine Historic Walking Tour offers a lively, offbeat way to explore the city’s past. It’s a smart choice for travelers who want to discover the city’s hidden stories without spending hours walking through museums or enduring dry narration. Instead, you get entertaining stories, local tips, and a friendly guide — all wrapped up with a visit to a cozy wine bar.

Whether you’re a first-time visitor or a seasoned local, this tour will add a playful twist to your understanding of St. Augustine. It’s perfect if you’re craving a lighthearted yet insightful look at the city’s colorful history.

FAQ

How long does the tour last?
The tour takes about 1 hour 30 minutes, making it a perfect short activity to fit into your day.

What is the price?
It costs $37 per person, which includes the storytelling and your group’s private experience; the wine bar start/end adds a nice touch.

Where does the tour start?
It begins at 11 Avenida Street, in the BART art and wine bar, a convenient spot in downtown St. Augustine.

Is the tour suitable for all ages?
Most travelers can participate, and it’s an easy walk, but keep in mind the stories have a naughty, adult humor side.

Are service animals allowed?
Yes, service animals are permitted, making it accessible for travelers with assistance needs.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund. Cancellations within 24 hours are not refunded.

Will it rain cancel the tour?
Yes, since it’s an outdoor experience, poor weather could lead to cancellation, but you’ll be offered a reschedule or full refund.

Is it a group or private experience?
This tour is a private experience, so only your group will participate, ensuring a personalized touch.

Can I book this tour last minute?
While last-minute bookings are possible, booking well in advance is recommended since most trips are booked about four months ahead.

To sum it up, the Secret St. Augustine Historic Walking Tour provides an engaging, humorous, and authentic peek into the city’s more mischievous side. With its focus on local legends, scandalous stories, and a relaxed pace, it suits travelers who prefer stories over textbooks and enjoy a spirited, social atmosphere. A perfect way to add some local flavor to your visit and leave with a smile.