: Step back in time with pastime private historical tours
Recommended by 98% of travelers
Badge of Excellence
St Augustine, USA
- 1 hour 30 minutes (approx.)
- Mobile ticket
- Offered in: English
Why travelers loved this
·
Explore our promoted experiences
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 344 reviews
Sort by: Most insightful
Julie_V, Jul 2026
Reggie was super great, so knowledgeable about the area and so relaxed. We loved it though it was a bit tight for three adults in the back and one up front.
Response from Host, Jul 2026
We’re so glad you enjoyed yourself and that Reggie is right on point. safe travels to you and your family and looking forward to your return.
Melissa_C, Jul 2026
There is a lot to learn about Saint Augustine. We enjoy learning with our tour guide Reggie. There was a lot of cool sites and he did a great job of telling us all about them.
Response from Host, Jul 2026
Thank you love the headline!
It’s a pleasure sharing this. City and Reggie is certainly one of the best. Thank you again very much.
Jennifer_S, Jul 2026
Reggie was amazing! He was very friendly and professional! He told amazing stories and let us take great pictures! This tour with Reggie is a must do!
Response from Host, Jul 2026
Thank you so much for taking the time to leave a wonderful review for Reggie and our company. We appreciate it very much. We hope you enjoyed your Fourth of July weekend and have safe travels when you return home.
Jack_M, Jun 2026
Cordial and knowledgeable adventure. I have visited St Augustine many times since 1950 ... and on this trip I learned several new things! Lots of fun ...
Response from Host, Jul 2026
That is saying a lot thank you for leaving your review. Hope you have a great Fourth of July.
kaye_w, Jun 2026
Reggie was a great tour guide. Tour was interesting and informative. Good overview of St. Augustine history.
Response from Host, Jun 2026
Thank you for sharing your review. What’s not like about Saint Augustine, right! Especially when you have a Tour Guide like Reggie.
Carrie_L, Jun 2026
Reggie was amazing and very knowledgeable. Definitely recommend as a start to your trip! Great way to get familiar with the area.
Response from Host, Jun 2026
Well said. We always recommend taking a tour when you first get to town saying layout of the land by a local. This will help you to have an insight of the things you’d like to do while you’re visiting. Thank you for taking the time to leave this review.
DrCarrie_C, Jun 2026
Reggie was AMAZING! Book this trip! We have done the trolley system before and it is not great because you are stuck on and off and it is so much time. When I learned about this place in an hour and a half with our tour guide was more than I’ve ever learned before. Worth every single penny.! Reggie until we meet again!
Response from Host, Jun 2026
That’s what I like to hear. We look forward to seeing you and your family and friends many times to come in the future until then may your whole family be blessed
Joseph_H, Jun 2026
The driver/guide was extremely knowledgeable about St. Augustine. He has spent and continues to spend hours in the Libraries researching everything St. Augustine.
Response from Host, Jun 2026
Thank you for taking the time to leave your review. You pointed out something that you realize the more we study and learn it makes it easy for us to want to share this newfound information keeping it fresh for not only you but ourselves as well.
John_M, May 2026
Best way to learn quickly about a new place. Activities, restaurants, etc. Plus lots of history and local info. Great investment of time and $ to make the rest of trip better!
Response from Host, May 2026
Couldn’t have said it better to take a tour no matter what city you’re in when you first get there with a local will give you a laydown of the City and the things you wanna do for the time that you’re staying we have museums. We have great architectural work here not to mention all the stories, including ghosts stories. We’re so glad you enjoyed yourself and I hope that you return soon.
Charlie_G, May 2026
Reggie was great. Explained everything with a passion. So much rich history in St. Augustine to see and have someone to explain it so well.
Response from Host, May 2026
Thank you for your review. We look forward to sharing all the rich knowledge of Saint Augustine each and every day and it never gets old because they’re so much to see.
Connie_E, May 2026
Our guide Reggie was awesome. He shared lots of history and hidden gems in the city. Would highly recommend.
Response from Host, May 2026
We’re so happy that you enjoyed yourselves and found yourselves in a truly unique and personable tour with Reggie who is soon becoming one of the great highlights of Saint Augustine himself. Look forward to seeing you and your family again have a great journey along the way.!
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!
Response from Host, May 2026
We so appreciate your review and that you had a wonderful time with not only Reggie but enjoying Saint Augustine and we look forward to your return
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 .
Likely to Sell Out
From $37.50
per personup to 24 hours before the experience starts (local time)
Compare Similar Experiences
Current
Likely to Sell Out
: Step back in time with pastime private historical tours
344
1 hour 30 minutes
Free Cancellation
From
$37.50
Customers Who Bought This Tour Also Bought
Explore Similar Things to Do
- Food Tours
- Half-day Tours
- Walking Tours
- Wine Tastings
- Beer & Brewery Tours
- Food & Drink
- Tours, Sightseeing & Cruises
- Private and Luxury
- On the Ground
- St Augustine
- Food Tours - Jacksonville
- Half-day Tours - Jacksonville
- Walking Tours - Jacksonville
- Wine Tastings - Jacksonville
- Half-day Tours - Daytona Beach
- Walking Tours - Daytona Beach
- Wine Tastings - Daytona Beach
Attractions in St Augustine, USA
- Oldest Store Museum Tours & Tickets
- Fountain of Youth Tours & Tickets
- Lightner Museum Tours & Tickets
- Spanish Military Hospital Museum Tours & Tickets
- Potter's Wax Museum Tours & Tickets
- St. Augustine Pirate and Treasure Museum Tours & Tickets
- Castillo de San Marcos National Monument Tours & Tickets
- St. Augustine Old Jail Tours & Tickets
- González-Alvarez House (Oldest House Museum Complex) Tours & Tickets
- St. Augustine Lighthouse and Maritime Museum Tours & Tickets
- Oldest Wooden School House Tours & Tickets
- Fort Matanzas National Monument Tours & Tickets
- Micro Masterpieces Art Gallery Tours & Tickets
- Father Miguel O'Reilly House Museum Tours & Tickets
- Medieval Torture Museum Tours & Tickets
- Mission Nombre de Dios Tours & Tickets
More attractions near St Augustine, USA