Saint Augustine: Walking Historic Tour

If you’re considering exploring Saint Augustine, Florida, and want a deeper, more authentic glimpse into its secrets and stories, this Walking Historic Tour by Freeedom Adventures might just be your ticket. Priced at $30 per person for about an hour and a half of engaging storytelling, this tour promises more than the usual history spiel—it’s packed with lesser-known facts, local legends, and some intriguing mysteries.

What makes this tour stand out? First, its focus on unusual stories and hidden secrets that often fly under the radar on standard city tours. Second, the knowledgeable guides seem to genuinely enjoy sharing their passion—and it shows, based on glowing reviews. The only caveat? It’s a walking tour, so you’ll want comfortable shoes, and the weather can be unpredictable. Perfect for history buffs, curious travelers, or anyone longing to see Saint Augustine through a more intimate lens, this tour is designed for those who love authentic stories and a personal touch.

Key Points

• Unique insights into Saint Augustine’s lesser-known history
• Compact group size (limited to 12) for a more personal experience
• Includes visual aids and picture references to enhance storytelling
• Accessible for most, including wheelchair users, with some considerations
• Rain or shine, making it a reliable option regardless of weather
• Great value for the depth of stories and quality of guides

You can check availability for your dates here:

An Overview of the Experience

Our team has not personally taken this tour but analyzed its details and reviews to provide a thorough, honest review. The emphasis on “secrets” and “unordinary history” suggests this isn’t just surface-level sightseeing. For travelers who have already done the standard tour circuit in Saint Augustine and are eager for fresh stories, this might be a perfect fit. It’s also ideal for those who value small-group intimacy—limited to just 12 participants—which offers a more relaxed, engaging environment.

The tour is designed to walk about a mile through the historic downtown, starting at the northeast corner of Cordova and Orange Streets. It winds through the old town, from Cordova Street, with stops and stories along Kings Street, through the historic plaza, and onto the bayfront. You’ll be on your feet for roughly 90 minutes, making it a manageable outing for most.

What to Expect on This Tour

The tour is structured around narratives that go beyond the basics. You’ll learn about the original name of Cordova Street and why it was notable, as well as where the Spanish buried their dead in the 17th century—stories seldom highlighted on regular walks. The guide will also explain why Memorial Presbyterian Church was built and who was behind it, adding layers to your understanding of local architecture and community.

Henry Flagler, the railroad magnate and hotel pioneer of Florida, plays a role here, with stories about his early efforts before constructing his beloved hotel. The tour also discusses Yellow Fever, illuminating how this deadly disease shaped the town’s history and development.

One of the most appreciated aspects noted by previous participants is the tour’s inclusion of visual references and picture examples—these make the stories more vivid and memorable. Expect to hear about local mysteries, science, cemetery tales, and even a touch of crime, all delivered in a friendly, approachable manner.

The Itinerary in Detail

Starting on Cordova and Orange Streets, the guide kicks off with the history of Cordova Street, formerly known by a different name, and what made it significant. As you walk down this historic corridor, the guide will point out features that are often overlooked but hold stories worth hearing.

Moving onto Kings Street, you’ll hear about notable buildings and their historical significance—some of which are tied to the town’s early settlers and its strategic importance during colonial times. The tour then takes you through the plaza and towards the bayfront, where stories of the town’s connection to the sea come alive. Expect to hear about Old cemeteries, including where the 17th-century Spanish buried their dead—stories that connect the past to the present.

Throughout the walk, the guide shares fun facts, such as why the Memorial Presbyterian Church was built (by whom and for what purpose). You’ll understand how Henry Flagler’s influence extended beyond just building hotels—what he had to do beforehand, and how his efforts transformed Saint Augustine into a tourism hub.

Yellow Fever is woven into the narrative as well—discussing how outbreaks impacted the town’s growth and health practices. The stories are not just dry facts; they are delivered with enthusiasm and a genuine sense of curiosity, making history come alive.

Why This Tour Offers Great Value

At $30, this tour offers exceptional value. It provides an intimate, guided experience that dives into lesser-known stories and local legends—something most visitors miss on larger, more generic tours. The inclusion of visual aids and reference photos enhances understanding and keeps the experience engaging.

The small group size ensures you’re not just another face in a crowd but part of a lively, personal conversation. You’ll gain insights not just about the buildings but also about the people, mysteries, and science that shaped Saint Augustine.

Participants have praised the knowledge and personable manner of the guides, especially noting how they share stories that aren’t widely circulated. One reviewer called Laura “excellent and very personable,” highlighting how her storytelling made historical details memorable.

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Practical Details and Tips

Tour Duration and Timing: Usually about 90 minutes, often available in the morning. It’s a convenient way to start your day or fit into a busy schedule.

Weather Preparedness: The tour runs rain or shine. Bring an umbrella or jacket if needed, and wear comfortable shoes—these are old streets, and you’ll be walking on uneven surfaces.

Accessibility: The tour is handicap accessible but note that some streets are tight or uneven. It’s suitable for most mobility levels, but if you’re unsure, contacting the operator beforehand might be helpful.

What to Bring: Comfortable shoes, water, an umbrella, and perhaps a camera—there are many photo-worthy moments.

Other Considerations: Gratuities are not included but appreciated. No alcohol or drugs are allowed.

Who Will Enjoy This Tour?

This experience is best suited for history enthusiasts, curious travelers craving stories beyond the standard guidebook fare, and those who appreciate small-group touring. It’s ideal for adults and older children who can stay engaged for 90 minutes and enjoy the storytelling.

If you’re someone who loves visuals and references, this tour’s inclusion of pictures will be a bonus. On the other hand, travelers expecting a fast-paced, high-energy activity might find this more subdued but deeply informative.

Final Thoughts

The Saint Augustine Walking Historic Tour provides a thoughtfully curated glimpse into the hidden tales and secret corners of this historic city. Its focus on lesser-known stories, the personal touch of guides, and visual aids make it stand out from more generic options. For those who want to connect more deeply with Saint Augustine’s past and enjoy a relaxed, engaging walk, this experience is well worth the price.

It’s particularly well-suited for travelers who have already seen the usual sights and are eager for stories that reveal the city’s intriguing mysteries and secrets. If you’re after a tour that combines history, local lore, and a bit of fun, this tour delivers on all fronts.

Frequently Asked Questions

Is this tour suitable for children?
While younger children might find it less interesting or challenging to follow, it depends on the child’s age and curiosity. It’s best for older kids or teenagers who can stay engaged for 90 minutes.

How long does the tour last?
Approximately 1.5 hours—on foot, covering about a mile through the historic district.

Is the tour wheelchair accessible?
Yes, it is wheelchair accessible, but keep in mind that some streets and sidewalks are old and narrow.

What should I bring?
Comfortable shoes, water, an umbrella, and sunscreen if needed. Always good to be prepared for weather changes.

Does the tour operate in bad weather?
Yes, rain or shine. It’s advisable to bring rain gear if rain is forecast.

Are tips included?
No, gratuities are not included but are always appreciated if you enjoyed the tour.

What part of Saint Augustine does the tour cover?
It starts at Cordova and Orange Streets and includes streets like Kings Street, the town plaza, and the bayfront.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours in advance, allowing flexible planning.

Is there a way to reserve and pay later?
Yes, you can book now and pay later, giving you flexibility in your travel schedule.

What makes this tour different from other Saint Augustine tours?
Its emphasis on hidden stories, secrets, and visual references, combined with small-group intimacy and engaging storytelling, sets it apart from more standard offerings.

This walking tour offers a true taste of Saint Augustine’s secret side, perfect for those eager to uncover stories that are often overlooked. With a knowledgeable guide, a relaxed pace, and a personal touch, it’s an experience that brings history alive—and makes your visit memorable.

You can check availability for your dates here: