: Step back in time with pastime private historical tours
Recommended by 98% of travelers
St Augustine, USA
- 1 hour 30 minutes (approx.)
- Mobile ticket
- Offered in: English
Overview
Discover St. Augustine's historical sites with ease, without the hassle of research or figuring out transport, during this private guided tour. Ride in a vintage vehicle with guides dressed in 1920s fashion as you cruise past landmarks such Castillo de San Marcos, Flagler College, and St. George Street in the historic district, while learning more about the sites than you would on your own.
- Great for small groups, up to four people can ride on this tour
- Hear haunted and historical tales of the city
- Ride in a vintage automobile with 1920s-themed guides
- Explore St. Augustine's historic district landmarks
What's Included
- Private transportation for up to 4 travelers for sightseeing on the site
Meeting and Pickup
Meeting point
- 11 Aviles St, St. Augustine, FL 32084, USA
Located in front of the Gail Nick art gallery
End point
This activity ends back at the meeting point.Itinerary
St. Augustine (Pass By)
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Service animals allowed
- Infants must sit on laps
- Most travelers can participate
- Price is for a group of 4 max
- This is a private tour/activity. Only your group will participate
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.9
based on 323 reviews
JudyButi_W, May 2026
Mr Reggie, was an outstanding St Augustine guide!!!
Will recommend to our friends to visit St Augustine and Reggie’s tour as the first stop!
Arlette_B, May 2026
This was an absolutely delightful way to become acquainted with the abundant, fascinating history of St. Augustine! The vintage vehicle was so fun- nice, smooth ride- and our guide, Reggie- was PHENOMENAL! He was so friendly and shared so many amazing facts about the city he clearly loves with a passion. It was a wonderful experience! Highly recommend this tour!
Response from Host, May 2026
We appreciate so much all the reviews. Thank you for your kind words Reggie as a phenomenal human being and we’re very happy to have them in such a beautiful city. Please come back again. There’s so much more to learn.
LoisandSteve_W, May 2026
Reggie was extremely knowledgeable about architecture, historical leaders of St. Augustine , and showing us unique features of the houses, walls, and the various sections of the city. He was also extremely kind and funny.
Response from Host, May 2026
Thank you for taking the time to leave your review. We agree Reggie’s phenomenal not only is he knowledgeable, but kind and funny.
Renae_M, May 2026
Reggie our driver was awesome! He was very well dressed. Extremely knowledgable and shared that knowledge in an unhurried and easily heard well articulated manner. Loved seeing and hearing about St Augustine. I would say it is a do again. Would definitely recommend.
Response from Host, May 2026
We appreciate your your review thank you so much. Reggie is an outstanding individual and guide of the city. We’re lucky to have him as you have found. We appreciate your comments and your praise for him and we look forward to seeing you again.
Taryn_H, Apr 2026
Please treat yourself and book this tour! Such a phenomenal way to experience St. Augustine! Reggie was a fantastic guide, showing us multiple hidden gems larger tours didn’t include. The tour was very interactive, with opportunity to ask questions along the way. Home run, highly recommend.
Response from Host, May 2026
We are so glad you enjoyed yourselves as you found Saint Augustine is an amazing place so much to see so much to do cleaning crime free and we can’t wait to see you come back again
Patricia_P, Apr 2026
Hidden Gem !!! The places you’ll visit n the history!!!! Reggie was fun, personal and knew so much about his town! Highly recommend a personal tour… Enjoy!!!
Response from Host, May 2026
As you can tell Reggie and our company, take a great pride in our city. How can you know? It’s absolutely beautiful along with all the mini guest we are blessed.
Jordan_B, Apr 2026
We've been on historical tours in Charleston, Savannah, and now St. Augustine. The small group atmosphere made it easy to hear the guide and ask questions, and the guide was excellent!
Response from Host, May 2026
Thank you so much for leaving your review not only does it help others help find us through your kind words, but it gives us a pride with each and every review
vera, Apr 2026
Was a great tour and Reggie was very knowledgeable and pleasant. We would come back and recommend to others.
Response from Host, Apr 2026
We so look forward to these types of reviews thank you so much for letting others know what a great time it is here in Saint Augustine
Ernest_M, Apr 2026
Be prepared to learn more history about St. Augustine than you thought you knew.
Our guide, Reggie, was amazing! He brought us through parts of St. Augustine that we would never have found on our own or have found online.
As a long time resident of this town, His thorough knowledge of its history and development is astounding. His tour was one of the best parts of our trip!
Response from Host, Apr 2026
Thank you so much for taking the time to leave this review. It really helps others have an understanding of our pride in this beautiful city of ours the history is amazing and there’s so much more that we can all learn even if you’ve lived here all your life so thank you once again I look forward to seeing again in the future
Rebecca_R, Apr 2026
Very enjoyable. Reggie was very patient with us, and very knowledgeable. Leisurely pace and very pleasant way to learn some of St. Augustine's history. Would definitely recommend and would definitely recommend Reggie. Thank you.
Response from Host, Apr 2026
We appreciate you taking the time to leave a review. It helps so many to understand what a beautiful city we have and how much we too enjoy telling people all about it.
Karen_Y, Apr 2026
Great tour of the city and stories of the city history. Visited spots we never would have on our own.
Response from Host, Apr 2026
We appreciate you’re not only leaving a great review but sharing with others they get to see and learn about things that most companies or trolleys just can’t offer. Thank you again. We hope you have a wonderful year and look forward to seeing you again soon in Saint Augustine.
NAHKOLE_W, Apr 2026
Reggie was amazingly knowledgeable. We learned so much and he was a great host. Definitely recommend this tour to learn a lot and see most spots in st. Augustine
Response from Host, Apr 2026
We so appreciate you taking the time to leave Reggie and our company. Such a wonderful review. We look forward to seeing you again as you visit this beautiful city.
Mike_B, Apr 2026
We're from Jacksonville and love to bring out of town friends to tour St Augustine via the Trollys... this was by far the best tour we've taken.. our guide Reggie was awesome 👌
Response from Host, Apr 2026
Thank you for taking the time to leave your review. We so appreciate it. Can’t wait to see you again.
Amanda_B, Mar 2026
Fantastic way to tour the city! Reggie was absolutely wonderful. The tour was personal and comprehensive with a distinct VIP feel. My Dad and I had such a special time enjoying the rich history, beautiful sites, and stylish auto. Highly recommend recommend!
Response from Host, Apr 2026
What a difference it makes when you take pride not only in your job but the environment you’re in the city is so beautiful. It brings beauty out in all of us.
Beverley_D, Mar 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.
Response from Host, Mar 2026
Thank you so very much for taking the time to leave this review. We’re not only take pride in our city our company but those that help us become successful like Don. He’s an absolute gym and we’re glad you got a chance to see our city and meet him.
Dennis_M, Mar 2026
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!!!
Response from Host, Mar 2026
What a fantastic review thank you so much. We appreciate all your kind words Reggie and our company strive to get better each and every day and with your help others are now seeing what pride we take in our cities and our jobs so thank you again and have a blessed day.
Carol_C, Mar 2026
Best tour ever. Reggie was the best. He was very knowledgeable and very interesting. You could tell he loves his job.
Response from Host, Mar 2026
You hit the nail right on the head! We love our jobs and this beautiful city. Thank you for your review!
Gwilym_L, Mar 2026
The tour is well worth it and our driver, Reggie, was well experienced with the city and the streets.
Response from Host, Mar 2026
Captain Reggie is amazing! We’re so very fortunate to have him on our team
Patricia_P, Mar 2026
Wonderful experience. Knowledgeable tour guide, personable, friendly. Highly recommend Reggie. Loved it
Response from Host, Mar 2026
Thank you so much for leaving your review not only does it help us grow as a company, mags a sense of pride to know that we’re doing a wonderful job .
Lorelei_S, Mar 2026
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!
Response from Host, Mar 2026
Thank you so much for taking the time to leave such a wonderful review. We’re glad you enjoyed yourself here in the city and we look forward to seeing you again and again and again.!
Katheryn_E, Feb 2026
OUR GUIDE WAS VERY KNOWLEDGEABLE. OT AMAZED US HOW WELL HE CONVEYED THE HISTORY OF THE TOWN. several of us had been to St Augustine previously but we learned and saw much more than on other trips. The only thing we would have liked any better is if he talked a little slower because we were all senior citizens. Great Tour.
Response from Host, Feb 2026
Thank you for taking the time to leave such a nice review for Reggie and our company so very glad you enjoyed yourselves .
Laura_A, Feb 2026
Driver was amazing and so informative. Took us to areas we had not seen any where else. Drive was comfortable and loved the car. Dressed for the event and seamless in his delivery. Would recommend and do this again.
Response from Host, Feb 2026
This is one of the best reviews I’ve read in quite a while thank you so much for taking that time. Reggie is phenomenal along with the charm of the city. We agree this is a great way to see the city.
Deborah_M, Feb 2026
This tour was so much better than we expected. Reggie was so entertaining, pleasant and informative. Our out-of-town guests were very impressed with the wealth of information Reggie presented. We’d definitely do this tour again!
Response from Host, Feb 2026
Thank you so much for taking the time to leave this wonderful review. We’re so glad that your guest enjoyed themselves here in the city. Reggie is phenomenal person and a top-notch tour guide. We’re very lucky to have him.
Clara_L, Feb 2026
Our tour guide Don was so knowledgeable and enthusiastic. We learned a lot of interesting local history. We thoroughly enjoyed it and would highly recommend it.
Response from Host, Feb 2026
Thanks for taking the time to leave this review. Don is an absolute gym and a sweetheart. The city makes it so easy to entertain folks like yourselves. We hope you enjoyed your yourselves throughout your entire day and we look forward to seeing you again.
Doug_H, Feb 2026
Reggie was an excellent tour guide! He really knew his history of the area and he presented it in a fun way! We liked his personality!
Response from Host, Feb 2026
Couldn’t ask for a better tour guide Reggie is exceptional. We’re so glad you enjoyed yourselves and look forward to seeing you again.
Anne_Z, Feb 2026
Reggie was a great tour guide. He clearly enjoys sharing his knowledge and love of the city! The car made it comfortable and very personal.
Response from Host, Feb 2026
Thank you for sharing your time with us. We provide our ourselves on exceptional guide guides and a very beautiful City. We’re so very glad that you enjoyed them both and that you look forward to return trip one day.
Audra_B, Jan 2026
Great tour guide and driver with respect and consideration for his guests. Very educational and informative.
Response from Host, Jan 2026
We’re so glad you enjoyed yourselves. . It was a pleasure to serve you and your family.
erin_p, Dec 2025
We loved this adventure through town and the history we learned. Donald was a wonderful tour guide and made this my daughters favorite thing we did while we were in town.
Response from Host, Dec 2025
We’re so glad you enjoyed your time with us the rich history of Saint Augustine and Don‘s wonderful charm. We wish you the best in the coming new year.
Grazina_C, Dec 2025
Had a great time really great way to get a history of St Augustine found out things that I didn’t even realize were true about the city.
Response from Host, Dec 2025
We’re so happy that you enjoyed yourselves with us. Saint Augustine is a beautiful and amazing city. We look forward to seeing you again.. happy new year to you and yours may be a blessed year for us all
Susan_H, Dec 2025
Was the best tour of our vacation! Driver Reggie was very nice and informative! Loved his love of the city!
Response from Host, Dec 2025
We appreciate your review how does it help us to succeed in the future but it’s the confirmation that we look for each and every time that we’re doing our jobs right? It’s easy to do your job when you have such a passion for such a beautiful city and it’s guests we would sincerely Like to extend our holiday wishes for you and your family that it may be a prosperous new year for you all
From $37.50
per personup to 24 hours before the experience starts (local time)
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