Step back in time with pastime private historical tours

There’s no more humorous mode of touring Saint Augustine than cruising around in our one-of-a-kind vehicles with our guides decked out in 1920s attire. You’ll soon turn into an attraction in our city as numerous other visitors often snap your photo and wave at you.

Duration: 1 hour, 30 minutes
Cancellation: 24 hours
Highlights
  • St. Augustine - A guided tour of the nations oldest city . Our tour guides will not only show the many historical sites but the story’s that go with them. Don’t miss out the best tour in Saint Augustine!
What's Included
  • Private transportation for up to 4 travelers for sightseeing on the site
Additional Information
  • Price is for a group of 4 max
Location
11 Aviles St
Aviles Street
Located in front of the Gail Nick art gallery
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(303 Ratings)
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Beverley_d
Mar 17, 2026
Our delightful, sunny, March tour 2026 - We enjoyed our tour with Dan/Don very much. He has a nice personality, and is very knowledgeable about St. Augustine history. The car was comfortable and it was a great way to spend some time.
Review provided by Viator
Dennis_m
Mar 15, 2026
Personalized tour of St Augustine in a 1920 Convertible Model T Ford - We went on the tour 3/14/26. This is an excellent way to learn about all the history that St Augustine offers. We experienced all the things that most tours encompass but went to many other points of interest that probably 90% of tours will not be able to get to because there are only 4 guests in the 1920 Model T car that easily gets in and out of all areas. Our host Reggie was phenomenal. He talked for the entire 90 minutes leaving us with some much information, that has given us reason to come back again, potentially many times to explore certain sites in more detail. He’s been a resident of the town for over 20 years and it’s evident he loves introducing guests to where he lives. We would highly recommend requesting Reggie if he’s available, you won’t be disappointed!!!
Review provided by Viator
Carol_c
Mar 15, 2026
Tour of historical St Augustine - Best tour ever. Reggie was the best. He was very knowledgeable and very interesting. You could tell he loves his job.
Review provided by Viator
Sunshine11131289843
Mar 15, 2026
Don’t hesitate. Great tour! We love Reggie! - Such a great tour! Reggie knows everything about the area and its history. We’d had a frantic travel experience and rushed to get there on time and they even offered pickup at the parking garage to help us out. It’s a great, relaxing ride in an awesome little car that can go places the bigger buses can’t reach. Fantastic experience, thank you!!
Review provided by Tripadvisor
Gwilym_l
Mar 14, 2026
Amazing drive and charismatic driver! - The tour is well worth it and our driver, Reggie, was well experienced with the city and the streets.
Review provided by Viator
Camper254520
Mar 12, 2026
It was the best ! We all loved it - Don was a exclusive tour guide very well informed with the local history with great jokes, loved 😍 the tour !!!
Review provided by Tripadvisor
Patricia_p
Mar 11, 2026
Great experience ! - Wonderful experience. Knowledgeable tour guide, personable, friendly. Highly recommend Reggie. Loved it
Review provided by Viator
Williamst915xr
Mar 4, 2026
Step Back in Time St. Augustine Tour - We had a wonderful visit and tour with Mr. Don leading our tour. His obvious love for his city and what he does made our tour of St. Augustine exceptionally awesome!
Review provided by Tripadvisor
Lorelei_s
Mar 1, 2026
Afternoon well spent! - We had a wonderful experience. Captain Reggie was such a gentleman and well informed. We learned a lot and because we were a small group he could answer all of our questions. We will do it again!
Review provided by Viator
Sunshine51705529726
Feb 28, 2026
Reggie and His Vintage Car - We had one more tour booked in our week long birthday trip for our 96 year old Dad. It made more sense to postpone it by one day and take the tour the day we were flying out so we didn't have to sit longer at the airport once we checked out of our hotel. They kindly accommodated our request and we went our last day before heading to the airport. Despite thinking we knew a lot about Saint Augustine having explored on our own and doing other tours, we were AMAZED how much we did not know or was not told on tours throughout the week. Reggie our vintage car driver was not only a true gentleman very concerned about safety, well being, and educating us all the while showing us a wonderful time. He had more information to share than all the encyclopedias ever written on Saint Augustine! He was absolutely remarkable! We saw SO MUCH, enjoyed a great afternoon in a meticulously clean and beautiful car, and he was so kind and patient with us, especially my Dad. We have been on many tours in Saint Augustine and throughout the country, Reggie by far was the best tour guide we have ever had! What a great tour, great car, great guide! SO VERY HIGHLY RECOMMEND!
Review provided by Tripadvisor
From $38
up to 4 guests
4 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).