If you’re planning a visit to St. Augustine and want to see the city with a personal touch, this private tour by Pastime Tours might just be what you’re looking for. It’s a relaxed, intimate experience that offers a unique way to explore the oldest city in the U.S. in a vintage-style vehicle, with a guide who’s as passionate about the history as he is about making sure you have a good time.
What we really love about this experience is how personalized it feels. With small groups—up to four people—you get the chance to ask questions and really soak in the stories behind the sights, not just snap photos from a bus window. Also, the ride itself, in a charming 1920s-style car, adds an extra layer of fun and nostalgia, enhancing the entire sightseeing vibe.
However, a couple of points are worth noting: this is a short, 90-minute tour, so if you’re expecting an in-depth exploration or a lengthy, comprehensive look at every corner of St. Augustine, you might find it a bit lighter on details. Also, since the vehicle is vintage and cozy, it might be less comfortable for larger or very tall travelers, as some reviews suggest.
This tour is well-suited for history buffs, couples, small families, or anyone who appreciates a personalized, relaxed way to get to know St. Augustine. If you enjoy engaging storytelling combined with a touch of vintage charm, this is definitely worth considering.
Key Points

- Small, Private Groups: Up to four guests, which means plenty of personal attention.
- Vintage Vehicle Ride: Adds nostalgia and fun, making sightseeing more memorable.
- Knowledgeable Guides: Guides are praised for their friendliness, humor, and historical knowledge.
- Personalized Experience: The tour is private, allowing for questions and tailored conversations.
- Convenient Pickup: From your downtown hotel, making logistics easy.
- Duration & Value: About 90 minutes at a reasonable price ($37.50 per person), offering good value for a personalized experience.
Exploring the Details of the Tour

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What’s Included and How It Works
This is a private tour offered exclusively to your group, which means no crowded buses or strangers sharing your experience. For $37.50 per person, you get around 90 minutes of guided sightseeing, expanded with the luxury of a vehicle and driver just for your party. Pickup from your hotel in downtown St. Augustine is included, making it simple to start and end the adventure.
The tour features a vehicle and guide dressed in 1920s style, transporting you through the city streets in a way that feels both charming and immersive. You’ll cruise around notable sites like the Castillo de San Marcos National Monument, Flagler College, the Old City Gates, and St. George Street. These are some of the most recognizable landmarks, and you’ll get a chance to see them from a comfortable, up-close perspective.
Itinerary Breakdown: What to Expect
The tour begins at 11a Aviles St, a historic starting point, and takes you on a scenic drive through the city’s prominent areas. While the route may vary slightly depending on traffic and your guide’s discretion, the core stops include key sites that tell the story of St. Augustine’s past, from its earliest days to more recent times.
Your guide—often noted for their storytelling skills—will share both the haunted tales and historical facts behind each place. For example, guests have raved about guides who are “very informative and personal” and “took time to answer questions,” making the experience feel more like an engaging conversation than a lecture.
The Vehicle and the Experience
The highlight for many is the vintage automobile. This isn’t just a gimmick; it genuinely enhances the sense of stepping back in time. Guests describe it as a “fun” way to tour and a “great old fashioned experience.” It’s a cozy ride, so it’s best suited for those comfortable in small, vintage-style cars. Some reviews point out that larger travelers might find it a squeeze, especially with four people onboard.
Guides and Personal Touches
It’s clear from the reviews that the guides are a major part of what makes this tour special. Don, in particular, gets glowing praise for his politeness, humor, and deep knowledge. Comments include “Don was polite, extremely informative, funny, and very accommodating” and “His charming personality along with his enthusiasm and knowledge made the tour a wonderfully enjoyable experience.”
Guests also mention how thoughtful guides are—some brought blankets on colder days or tailored the experience to specific interests. This personalized approach makes a big difference, especially if you’re celebrating an anniversary or traveling with family members of varying ages.
The Value of this Tour

At $37.50 per person, this private tour offers excellent value, especially considering the personalized service, direct transportation, and the chance to ask questions along the way. Compared to larger group tours or trolley options, the intimacy and flexibility here stand out. Many reviews highlight how memorable and engaging the experience was, with guests saying it was “the best tour in Saint Augustine” and “definitely worth doing.”
What the Tour Might Not Be
If you’re seeking an exhaustive, in-depth historical account or a lengthy exploration of every corner of St. Augustine, this might not meet your expectations. It’s a shorter, more relaxed overview, ideal for a quick yet personal introduction to the city. Plus, since the vehicle is a vintage style, it might be a tight fit for larger or taller travelers, which is something to consider if comfort is a priority.
Who Should Book This Tour?
This experience is perfect for couples, small groups, or families looking for a relaxed, engaging way to discover the city’s highlights. If you enjoy storytelling, historic sites, and a fun vintage vibe, you’ll love it. It’s also fantastic for those who prefer a private, unhurried experience over larger, bus-based tours.
It’s equally suited for visitors celebrating special occasions—like anniversaries—since the personalized attention and cozy vehicle add a romantic touch. Travelers who enjoy a bit of humor and personable guides will find this tour particularly delightful.
Frequently Asked Questions

Is this tour suitable for children?
While the tour isn’t specifically marketed as a family activity, the short duration and engaging storytelling can appeal to older children and teenagers. However, very young children might find it less interesting or uncomfortable in the vintage vehicle.
Do I need to book far in advance?
Yes, most travelers tend to book about 24 days ahead on average, which suggests spots can fill up quickly, especially during peak seasons.
What does the tour include?
You get a private, guided drive through the historic district, transportation in a vintage car, and pickup from your downtown hotel. The guide shares stories and provides a personal touch.
Can I cancel if my plans change?
Yes, there’s a free cancellation policy up to 24 hours before the tour. If you cancel earlier, you get a full refund.
How long does the tour last?
Approximately 1 hour and 30 minutes, making it a perfect short activity that fits into a day of sightseeing without feeling rushed.
Is the experience weather-dependent?
Yes, it requires good weather. If canceled due to bad weather, you’ll be offered a different date or a full refund.
: Step back in time with pastime private historical tours
“Very informative and personal. Took time to answer our questions. You could Tell he has a real love for the area and the history of it.”
Final Thoughts
This private tour from Pastime Tours offers a charming, personal way to see St. Augustine. The combination of knowledgeable guides, a vintage vehicle, and a focused itinerary makes for an engaging experience that feels both relaxed and rich in stories. It’s especially well-suited for couples, small groups, or anyone wanting a low-pressure introduction to this historic city.
While it’s not the most in-depth tour out there, the personalized nature and fun aesthetic make it memorable. If you appreciate stories told with humor, enjoy vintage styles, and value a private experience, this will likely be a highlight of your trip.
For travelers who want good value, friendly service, and a cozy, tailored glimpse of St. Augustine’s past, this tour hits all the right notes. Just remember to book early, dress comfortably, and be ready for a delightful ride through history.
Happy exploring, and enjoy your time in St. Augustine!
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