St. Augustine Private History Tour Review: A Fun Way to Explore America’s Oldest City

Despite growing up in east central Florida, I just did my first St. Augustine private history tour. While I had visited the fort as a kid, I had never truly experienced a tour of the historic district of St. Augustine.

My friend and her two daughters joined me, making it a group of four. The perfect size for this Pastime Tours private history tour. We also figured riding around would be better for her 10-year old daughter and as someone who has gotten restless on walking tours, I think it was the right call.

We all enjoyed the tour! The history presented started immediately, but after a few minutes we were able to start digesting some of it. Overall, I recommend it, but there are definitely a few things to keep in mind.

In this St. Augustine Private History Tour Review, we’ll discuss our experience, things to keep in mind and help you determine whether this tour is a good fit for your St. Augustine itinerary!

What Is the Pastime Tours Private History Tour in St. Augustine? (Quick Background)

If you’ve been to St. Augustine before, you’ve probably seen the usual suspects like the trolley tours, the ghost walks, the hop-on-hop-off buses packed with tourists.

Pastime Tours is a small, private guided tour company based in St. Augustine that takes you through the city’s rich history in a way that actually feels personal. Instead of shuffling through the streets with a crowd of strangers, you get a dedicated guide offering an experience that can be tailored to your group. It’s the kind of tour where you can actually ask questions, slow down at the spots that interest you, and have a real conversation about what you’re seeing.

What really sets them apart though is the concept. The tour is built around a 1920s-style Model T experience, so you’re not just learning about history, you’re kind of riding through it. It adds a fun, old-school charm that makes the whole thing feel more immersive than your average sightseeing tour.

I found them through Viator, which is where you can check availability and book if you’re interested. They offer different tour options, so it’s worth browsing to see what fits your group best.

If you’re looking for the best private tours in St. Augustine and want something a little more unique than the standard options, Pastime Tours is definitely worth a look, and I’ll get into exactly what the experience was like in the next section.

What to Expect: The Tour Experience

So let’s get into this St. Augustine Private History Tour Review and discuss what happens when you show up, what you’ll see, and what the vibe is like from start to finish.

The Basics

The tour runs about 90 minutes, which I think is actually a great length, especially if you are only spending one day in St. Augustine. It’s long enough to cover a lot of ground and really soak in the history, but not so long that you’re begging for it to end. We never felt rushed, but we also weren’t dragging at any point.

Because it’s a private tour, it was just our group which included me, my friend, and her two daughters. No strangers, no waiting for other people to catch up, no competing for the guide’s attention and no walking in the heat (and yes, it was hot that day in early March). That alone makes a big difference in the overall experience.

The Guide

Honestly, the guide made the tour. The depth of knowledge was impressive and Reggie’s love for St. Augustine was evident. It felt like we were getting the inside scoop from a knowledgeable local, who loved history. We asked questions throughout and always got thoughtful, detailed answers, which I really appreciated.

What You’ll See

St. Augustine has no shortage of history to cover, and the tour doesn’t skip the good stuff. You’ll pass by and learn about some of the city’s most iconic landmarks, including:

• Castillo de San Marcos — the 17th-century Spanish fortress that still stands on the waterfront
• Flagler College — originally the luxurious Ponce de León Hotel, built by Henry Flagler in the 1880s
• The Old City Gates — one of the most recognizable landmarks in the historic district
• St. George Street — the heart of old St. Augustine, lined with historic buildings and colonial-era architecture

The private tour format really shines here because if something caught our eye or sparked a question, we could just… ask. There’s no pressure to keep moving for the sake of a larger group.

The Private Tour Difference

I want to emphasize this point because I think it’s the biggest selling point of booking a private guided tour in St. Augustine over a group option. The conversation is two-way, and the guide was great about answering questions when we had them. That kind of flexibility just doesn’t exist on a shared tour, and it made the whole experience feel a lot more engaging and personal.

We were also able to request a drop-off spot within the historical downtown that differed from our pick-up location. This is definitely not something offered on a regular tour.

Check Availability for Pastime Tours: Step back in time with pastime private historical tours

Our Experience on the St. Augustine Private History Tour

Our guide, Reggie, picked us up at the Visitor’s Center, which is near the parking garage. We arrived about 20-minutes early and were able to use the restroom in the visitor’s center.

It wasn’t difficult to find our tour guide, since he pulled up in a 1920’s style vehicle. There were no windows on the side and the seat was basic bench seating, but still comfortable. Reggie introduced himself and opened the doors for us to climb in.

Sights & History

Reggie wasted no time in diving into the rich history of St. Augustine, but I have to admit that it took me several minutes before I could start digesting it. He spoke fast as he showed us the landmarks and shared their history.

We drove by Flagler College as he explained the history of what Henry Flagler built. Making our way to Lightner Museum, he continued spitting facts though I was finally starting to catch up to his pace. The St. Augustine history was coming to life.

We also saw two cases of an oak tree with a palm tree growing out of it. I remember seeing them as a kid, and loved seeing this phenomenon again as an adult.

From the Lightner Museum we made our way to the local neighborhood nearby. I loved this part of the tour as I don’t think I’ve ever been to this area of St. Augustine. He explained the role St. Augustine played in Black history and in the Civil Rights Movement, which I found very interesting!

Our guide eventually made his way around and we passed the Fort. From there we stopped at Ripley’s Believe It or Not, which I learned is the original! We got to get out here to see the first ever mobile home made out of a tree trunk.

Then we headed to the Mission Nombre De Dios. This was a place I had wanted to visit, so I was so happy we got to stop here. The chapel is adorable and the gardens are so peaceful. We got to explore for a bit, and we loved it so much, we returned later that afternoon to explore more.

Our guide then took us by the Fountain of Youth entrance and we got to enjoy the beautiful canopy of trees on Magnolia Avenue. We appreciated the guide made sure we were able to get a decent picture of this charming street.

Our final drive by took us near St. George Street. We requested to be dropped off by Lightner Museum, which is a bonus of taking a private tour!

What We Loved

Since we were a group of four, this was such a great value! It was less than $40 per person for the day we visited in March.

It was nice being able to ride around, especially since it ended up being a hotter day than I expected. I’ve done many walking tours over my travels, and they are way more tiring with all the standing you end up doing. This also meant we had plenty of energy later to walk around.

We also loved being able to ask questions if we wanted. The guide offered a lot of information and it was great being able to ask without worrying about anyone else getting annoyed.

A Few Things to Keep in Mind

The vehicle is open, so there’s no air conditioner. The day in March we did the tour was warmer than I was expecting, but nowhere near the heat of a Florida summer. Keep that in mind if you visit during our hottest months.

Additionally, consider the time of day you book the tour. If you do book in the summer, thunderstorms tend to roll in more often in the afternoon, so book a morning tour.

The private Pastime historical tour is very educational and informative, which can get boring for kids. However, riding is more fun than walking so that’s a good tradeoff!

Book as a group of four to get the best value: Pastime Tours: Step back in time with pastime private historical toursPastime Tours: Step back in time with pastime private historical tours.

Is It Good for Families with Kids?

If you want to do a historical tour on your St. Augustine itinerary, this private tour is definitely worth considering over others. While any historical tour would be information heavy, the ride adds a fun element.

Even as an adult, it felt like information overload at times. If the 10-year old’s mind didn’t wander I’d be shocked. However, the ride is far less tiring than a walk and she definitely enjoyed the two stops we made as well.

Overall, if you really want to do a historical tour in St. Augustine, I would definitely recommend this one. However, just remember it’s not super interactive, but will be more enjoyable than a walking tour for kids.

Tour length: ~90 minutes | Group size: private up to 4 people | Book via Viator: Pastime Tours: Step back in time with pastime private historical toursPastime Tours: Step back in time with pastime private historical tours

St. Augustine Private Tour vs. Walking Tour — What’s Better?

I’ve done walking tours in so many cities around the world. While I enjoy them, I can say the standing around gets tiring. What I loved about this private St. Augustine historical tour is the ride kept it fun and saved our energy so we could explore later on our own.

One major difference is location. A walking tour will focus on a smaller area, while the riding tour took us much further. We then were able to decide if we wanted to return to any spots later and we did return to the Mission Nombre De Dios!

Ultimately both options are great and affordable, so it just depends on preference.

For a fun ride loaded with history: Pastime Tours: Step back in time with pastime private historical toursPastime Tours: Step back in time with pastime private historical tours.

Final Verdict: Is This St. Augustine Private History Tour Worth It?

Yes! I really enjoyed this St. Augustine Private History Tour and learned so much about America’s oldest city. A place I’ve been many times since I was a kid, and yet I still learned new things!

I loved being able to ride around, and having energy leftover for strolling St. George Street later. Of course, we definitely stood out and became part of many tourist photos.

The guide offered a lot of great information, way more than I could fully keep up with. Of course, the lack of historical information is what disappointed me about the St. Augustine food tour, so I am happy there was no lack of history with this experience.

This St. Augustine Private History Tour is a great value and a fun way to learn more about the history of America’s oldest city.

FAQ

Final Thoughts: St. Augustine Private History Tour Review

I hope this St. Augustine Private History Tour review was helpful in deciding if it’s right for your St. Augustine trip. The tour taught me things I didn’t know and was such a fun way to get around!

The oldest city’s history cannot be condensed into 90 minutes, but our guide certainly made an effort to cram as much in as possible! Plus we got to see places we had never seen and learn more about them.

Overall, I recommend this Pastime Tour of St. Augustine and if you have a group of four it’s such a good value! I hope you have a great time exploring this historic Florida town!