St. Augustine Old Jail Tour: Uncover Dark History in 30 Mins

Very interesting. Our tour guy was very enthusiastic and did a great job! I was afraid it might be a bit cheesy — it was not.

Lizzy was our tour guide and she was outstanding! I loved the way she interacted with the guest. She was very knowledgeable and really helped the guests to understand what being sentenced to that jail would have been like. It's amazing to think that it stayed operational until the 1950s.

One thing I will say is that the presentation of course depends on the presenter, the one running the show, giving you the information, and keeping you entertained and engaged. Our guide was a bully to guests on the tour. There’s playing a character role and there’s reading the room. Calling people four eyes, bald-e-locks, and other names was very childish. We returned to the jail during the ghost tour and had a different guide and he was very engaging. So it just depends on which tour guide you are paired with. The history I learned was interesting.

It’s a short tour, and has some cool stuff to see, and stories to read about. I was excited to do this tour with our kids, after reading reviews. I will say that it may be better with a different guide. Our fella was stiff, awkward and couldn’t seem to find the balance between sharing historical facts and being funny. At one point, I was searching for the exit and wishing for escape… I wish we could have just explored on our own the whole time, honestly. Anyway, maybe try to find out which guides are good before you go? (And for the managers, definitely do more training and help your guides with crowd wrangling and their patter). Our guy was having the “off-est” of off days. Anyway, NOT worth the money.

Boss Benny from the Bronx was the best! Great fun , interactive tour which immerses you in the experience of that time. Lots of historical information pertaining to the jail and the region.

Our tour guide Boss Benny was amazing. He belongs on Broadway. Not only did he tell us the history, he sang us a song about the suffering of the prisoners. Best tour in St. Augustine!!

The tour itself was really good. Unfortunately our tour guide let his political beliefs be known throughout the tour. Having a family divided, this made the tour very uncomfortable for us. We all just wanted a weekend away without having to deal with this.

We were visiting from NH. This is a very fun tour. Tour guides are really into their job. The history and photos of the jail are something to see. Good learning experience.

Our tour guide was Lizzie. Don't ask her if she is Lizzy Borden, lol. Being incarcerated was obviously no picnic back in the day. Definitely an eye opening tour.

Our guide, Clarence T, was amazing at his job! Very entertaining and made the tour super fun! He brought the rich history to life with his portrayal of an inmate. Definitely worth the time.