If you’re looking for a way to explore St. Augustine’s legendary past without the typical tour bus crowd, a private guided walking history tour might be just what you need. From pirates to colonial settlers, this tour promises an engaging experience that’s both educational and fun. We haven’t done it ourselves, but the glowing reviews and detailed itinerary suggest it’s a solid pick for anyone wanting a personalized glimpse into the city’s storied streets.
What really catches our eye about this tour are two things: the personalized attention that comes with a private guide and the hands-on activities that make history come alive. Kids especially seem to love holding artifacts like cannon balls or trying on pirate gear, which turns learning into a memorable adventure. On the flip side, a possible consideration is the duration—at around 1 hour 30 minutes, it’s a reasonably short tour, but for those wanting a full day of exploring, this might just be a snippet.
Who’s this tour best suited for? If you’re traveling with family, history enthusiasts, or anyone who appreciates a more personal, interactive experience, this could be a highlight of your trip. It’s also a good choice if you want a flexible, private outing that allows you to ask questions at your own pace.
Key Points

- Personalized Experience: Private tours mean you’ll get a tailored experience with direct interaction from your guide.
- Educational & Fun: The mix of storytelling and hands-on activities like artifact exploration keeps all ages engaged.
- Convenient and Flexible: The tour ends back at the starting point, and the private booking ensures a more intimate setting.
- Cost-Effective for Families: At $40 per person, it offers good value for a personalized, museum-quality experience.
- Accessible & Easy to Join: Near public transportation, with mobile tickets, making planning straightforward.
- Short but Sweet: The 1.5-hour duration makes it manageable for most schedules, especially with kids.
Exploring the Itinerary: A Step-by-Step Breakdown

Interested in history? Here are other past-focused experiences we've examined in St Augustine
Starting Point: 76 Spanish St
The tour kicks off at a central location, making it easy to find and ideal for those staying nearby. You’ll meet your guide here, ready to set out into the historic streets of St. Augustine.
The Oldest Wooden Schoolhouse (Brief Stop)
A quick 5-minute stop here introduces you to the city’s earliest educational building. While brief, it sets the tone for exploring the city’s deep roots. It’s a neat spot that many find photogenic and evocative of simpler times.
Lightner Museum & City Hall (10 Minutes)
Walking past these landmarks, your guide will likely share snippets about their historical importance. The Lightner Museum is renowned, but note that entry isn’t included, so if you want to explore it afterward, plan accordingly.
Government House Museum (5 Minutes)
Situated on the Town Plaza, this stop gives a quick glimpse into St. Augustine’s colonial past, specifically during the Spanish occupation. It’s a free stop, making it a nice, no-stress addition to your walk.
If you're drawn to exploring St Augustine on foot, we've looked into these other walking experiences
Castillo de San Marcos National Monument (10 Minutes)
Here’s where the tour really ramps up. Your guide will give a brief overview of the fort’s role in the city’s defense and survival. Although admission isn’t included, you’ll get a feel for its significance and can explore further on your own if interested.
What You Can Expect from the Tour Experience
While the itinerary covers some key sights, the real magic lies in how your guide brings history to life. The reviews mention engaging personalities, which makes a big difference in keeping everyone interested. The focus on storytelling, combined with interactive elements—like holding a cannonball or examining artifacts—means you’re not just listening but participating.
One reviewer highlighted how the explanations were tailored for children, making it accessible and fun for the little ones. Another loved the treasure hunt and candle making, which transforms a simple walk into a playful expedition. These activities seem to resonate well with families, but they also add a charming layer of fun for adults who enjoy a bit of whimsy.
The Value of a Private Guided Tour

For $40 a person, you’re not just paying for a walk; you’re investing in a curated experience. The guide’s insights and the ability to customize your pace and focus make this a more meaningful visit than a typical self-guided stroll. Plus, since it’s private, your group’s questions and interests can shape the conversation.
The reviews back this up, with one guest saying it’s “the best activity for young children and families.” The guides are praised for their personalities and ability to adapt, making a potentially dry subject engaging and lively.
What Are the Downsides?

The main consideration is the duration—around 90 minutes—which might feel a bit short if you’re eager to see every corner of St. Augustine. Also, some stops, like the Lightner Museum, require additional tickets if you want to go inside, so budget for that if interested.
Since the tour is a walking experience, comfortable shoes are a must, especially if you’re exploring on a hot day or with children. Lastly, because the tour covers some outdoor areas, weather could affect your experience, so check the forecast.
Who Is This Tour Best For?

This private tour appeals most to families, history lovers, and those wanting an intimate, flexible experience. It’s especially suited for travelers with children who enjoy hands-on activities and storytelling. If you prefer large group tours or want a comprehensive day-long itinerary, this might feel a little limited. But for a relaxed, meaningful snapshot of the city’s past, it hits the mark.
Final Thoughts

In a city as historic as St. Augustine, a private guided walking tour offers a personalized lens into its stories, from pirates to colonial governors. The combination of storytelling, artifacts, and interactive elements makes it more than just a walk; it’s a mini adventure. The high marks from reviews speak to guides who are knowledgeable and engaging, making history accessible and fun.
The experience is a great fit if you enjoy tailored tours that respect your pace and interests. It’s especially good if you’re traveling with family and want to keep everyone entertained. While it might not be the most exhaustive tour in town, the quality and intimacy of this experience make it worthwhile.
If you’re after a memorable, educational outing that avoids the crowds and keeps all ages engaged, this tour could be a highlight of your trip to St. Augustine.
Private Guided Walking History Tour
“The explanation of the history of pirates and privateering tailored specifically for toddlers and young children, the candle making, the treasure h…”
FAQ
Is this tour suitable for children? Yes, reviews mention that it’s particularly good for young children and families, with activities tailored to engage kids.
How long does the tour last? The tour lasts approximately 1 hour and 30 minutes, making it a manageable outing without being too lengthy.
What stops are included in the tour? Stops include the Oldest Wooden Schoolhouse, Lightner Museum, Government House Museum, and Castillo de San Marcos, with brief visits and explanations at each.
Are admission tickets included? No, admission to the Lightner Museum and Castillo de San Marcos is not included; you can visit these places afterward if interested.
Where does the tour start? It begins at 76 Spanish St, St. Augustine, which is centrally located and easy to find.
Can we cancel if our plans change? Yes, you can cancel free of charge up to 24 hours before the tour, ensuring flexibility.
Is the tour private? Yes, only your group participates, giving you a more personalized experience.
Is transportation provided? No, this is a walking tour, so wear comfortable shoes and be prepared to stroll.
What is the price? The tour costs $40 per person, offering a good value for the personalized experience and interactive elements.
How do I book? Most bookings are made about 8 days in advance through the provider, See America Tours.
If you’re curious to explore St. Augustine’s history in a lively, interactive way, this private guided tour offers a thoughtful blend of storytelling and hands-on fun. It’s suited for those who value personal attention and a relaxed pace, all while uncovering some of the city’s most iconic sights.
More Walking Tours in St Augustine
More Tours in St Augustine
More Tour Reviews in St Augustine
- Dolphin, Manatee and Sea Turtle Kayak Adventure
- Private Golf Cart Tours, LLC in St. Augustine
- Ancient City Tarot Walk and Ghost Stroll in St. Augustine
- Old City Ghosts: Phantom Pirates & Poltergeists Tour
- Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
- Booze and Boos Haunted St. Augustine Ghost Walking Tour
More St Augustine experiences we've covered
- Private Guided Walking History Tour
- Private Golf Cart Tours, LLC in St. Augustine
- Ancient City Tarot Walk and Ghost Stroll in St. Augustine
- Old City Ghosts: Phantom Pirates & Poltergeists Tour
- Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
- Booze and Boos Haunted St. Augustine Ghost Walking Tour
- Shared Minibus Tour in Historic St. Augustine
- : Step back in time with pastime private historical tours
- St. Augustine Walking History Tour
- Riding Through History of St.Augustine: Premium Tour with PiCk Up
- Freeedom Photo Adventure Experience In St. Augustine
- Ghosts of St. Augustine Walking Tour
