Brooklyn Benny was super entertaining during our tour. My girlfriend and I were lucky enough to be the only 2 people on our tour (the next group was huge so I don't know how we got so lucky), so we got a very personalized experience. His wealth of knowledge and sense of humor were on point. Highly recommend! Tip: do the Ghost & Gravestones tour at night and you get to go back to the jail for a haunted tour! read more

Old Jail Museum - Ghost & Gravestones Tour - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

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**ACTUAL JAIL NOT A REPLICA** As our (actual) freedoms have been restricted, limited and in some states taken away...I wasn't really feeling the whole visit a JAIL on my vacation from being restricted. Any other time I would have enjoyed this interesting experience but I was very uneasy and just couldn't get comfortable. We've been locked up at home ( covid planned-demic)and this is just too soon. The gallows, the cages... oh goodness, so sad and cruel However, for historical value -and education- it's good because you're learning in an immersive setting. The guide, Jack was very good and funny. He actually knows a lot so ask him anything. I'm actually glad I did it. A little harsh for certain younger children but still important to know. If you're afraid of crowds just avoid it because even though they make you wear a mask you'll be rubbing elbows with the group. There's not any room for any distancing ok? Now you know! read more

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It was nice doing a little tourist stuff at the back end of a successful visit to this area. Most of this was done driving through the area; I couldn't ask for a better tourist guide; this place was pretty cool as a photo showing some of the history of this community. Everybody here is very welcoming that encountered, Well after being stuck in the house for close to a year because of the pandemic, people should be dancing in the streets have some resemblance of life back. Since I'll be working on a project in this area for a while, I can't wait to come back here to check on my project and spend a little more time with my tourist guide and the lovely people in this community. In short, do I recommend this place? Absolutely 100%, I wanted to come here for the past six months and had some resistance, but I'm sure glad I came this time read more

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Mable did a great tour and was so much fun. If you really enjoy learning about the past I would absolutely recommend this tour.

Visited the Old Jail while sightseeing in St Augustine. The mail is rich in history. We especially loved the crime artifacts throughout the mail. Our guide Bobalew was fantastic. read more

Boss Benny is fantastic!! Great tour, Benny was very knowledgeable about the jail and jail life. We really enjoyed talking to Benny after the tour. Highly recommended! Stay safe out there Benny ! read more

Old Jail Museum - I met my heart in Jail! - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

I come down to St Augustine a few times per year to visit family, and this time we decided to check out the jail. Although it's a small place, our tour didn't feel too short as it was packed with a great mix of interesting history and jokes to keep it light. Boss Benny made it a really fun experience for us! Would definitely recommend this to others. read more

My favorite place to take out of town guests when in Saint Augustine. Everyone we've gone here we've had a great time with professional officers of the law showing us the jail. Today it was Mr Slaughter. We've been here at least 5 times in the last 10 years and Mr Slaughter made the tour as enjoyable as the first. This is a must do if in Saint Augustine for a short time. I promise iit will be worth the few dollars you pay to enter. The jail was built by the same company who built Alcatraz but is much smaller in size. The jail has a front porch on the front which in the old days made people think it was a hotel and not a jail. Once inside, you will know what it really was used for. Many fun photo opportunities for kids to college age friends to life long friends. Great history and educational too. A Saint Augustine must do. Owned by the Trolley company and available as part of a money saving package deal with the trolley. read more

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Enjoyed our experience here. We decided to visit on our second day in St. Augustine. All "jail inmates" were amazing. They were entertaining, yet professional, and very friendly. Bucky and Wiley were the BEST ever!!! Our favorite part was the interactive play outside the building with our children. This was a fun time for sure. The inside of the jail was neat to see as well. We didn't like having to put face masks on in order to visit, but decided that we would do it. It caused us some difficulty with not breathing so well in the heat, but we made it through ok. We'll definitely visit again, but will wait until the face mask rule is gone. Thank you for having us! read more

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So upset to hear that our favorite tour guide Bobalew is no longer doing the Old Jail tours. A year ago, two days after moving to Florida from Arizona, after barely unpacking our boxes and getting settled we went to St Augustine. The very first thing we went out and did here in Florida was the Old Jail Tour with Bobalew, He and his character will always be a core memory and an integral part of our first experiences here. He was engaging, funny, educating, and you can tell he loved what he did. Being now locals, we go to the old town area often. We would have been constant returning customers to the Old Jail if they didn't let him go. Whatever the disagreement, Bobalew belongs in that role, he was meant to give people the kind of memorable experience that he was able to give me and my family through his hilarious character. I hope the management is able to realize the value of the person they lost. Hire him back! He's a staple of that place now, he deserves whatever he asks for and substantially more, and probably an apology or three! +5 stars for our original experience with Bobalew at the Old Jail. Let him back, I'll give you back the 5. read more

Must See! Rich History! If you're ever in the area you should definitely stop by for a quick trip back in time!

Our guide Benny at the Old Jail Museum was great! Super funny, while being very informative. Would definitely come again and highly recommend! read more

Interesting spot! Definitely worth a stop if you're ever in the area! The kids loved it and lots of cool and interesting facts! read more

Old Jail Museum - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

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This was an excellent tour! After our trolly tour we had tickets to tour the old Jail Museum. We stood outside the jailhouse waiting for the tour to start. A man dressed up like a sheriff came and took everyone's tickets. Our tour guide was amazing. He was dressed like a jailbird and talked like one too. He really played the part well. He made the tour so entertaining and informative. He took us all around the outside of the jailhouse to the back and showed us where the gallows were and the big hanging tree. Then he took us inside the jail. He made all the women get into a jail cell and closed the door which was quite funny. As we toured the jailhouse he told some very interesting stories. He kept everyone's interest. Even the little kids were having a fun time. This is an excellent tour for all ages. FYI There are stairs to climb on this tour. read more

Old Jail Museum - Our tour guide. - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

This historical jail was a harsh reality of how inhumanely people were treated. Yes, of course jailers shouldn't be given special treatment but at least treat them as humans and not animals. The fact that treatment and conditions were so horrible the warden should've been ashamed of himself. Anyhow the tour itself is very interesting and kinda spooky. They give you a tour from top to bottom and all items inside including furnishings, photography, gadgets, paperwork, kitchen and jail cells are all original so no touching allowed. There is even a story of a famous jailers hanging with pictures they put in a different room to be respectful to those who wouldnt want to see tbat..I chose not to see, the story was enough for me. I think history is important regardless of the good, bad, and in between. Facts are facts and If your a historical buff, interested, or even just curious I say to take the tour, just be careful with the little ones, maybe a bit to much for them. read more

Had a great time at the Old Jail House today. Bobalew was the best! He's very knowledgeable and funny and made the tour our favorite one in St. Augustine so far. read more

Cornelius was a great tour guide- he was funny and very knowledgeable. He made our experience a 10/10. We loved visiting and learning about the Old Jail. read more

Mabel was wonderful! Very informative, funny, and kept it interesting. Even though Marge kept trying to touch stuff lol

Guided tour of the oldest jail in Florida. It was active in St. Augustine for many years. Great tour guide, lots to see, and very interesting for history buffs and anyone in general. You can see the cells and replicas of many important facets of daily prisoner life. Personally I had a great time and highly recommend it. Tour guide was very charismatic and knowledgeable. Good times! read more

Old Jail Museum - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

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Great visit to the jail by Bobalu, he did a great job of guiding us through the various parts of the tour.Bobalu had a great sense of humor on a very serious topic of incarceration during the 1900's! A lot of history to explore and very realistic interpretation of what it was like to be in jail in St Augustine in the early 1900's!! Plenty of parking and a lot to explore in the immediate surroundings. read more

Awesome experience! The tour was very informative and our hilarious tour guide Patrick made the experience even better. It was interesting to learn about the location and Mr.Flagler. My FAVORITE parts were learning about the kitchen and some of the death row inmates! read more

Old Jail Museum - Jail Cells - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

We decided on the very last day of our trip to pop in and see what the old jail had to offer, didn't expect much at all but figured it was worth checking out since we had done basically everything else Saint Augustine had to offer.. and we're beyond pleasantly surprised to have had a GREAT TIME. Dare to say this was probably our favorite attraction of the trip. Mainly because our tour guide Bobalew; He was so animated! Interesting to listen to AND funny. He was more than happy to answer questions, ask us questions to keep it interactive and really spend some quality time with us to give us the history of this old jail. Amazing how well it was preserved and crazy to think people were imprisoned there. Highly recommend! read more

Old Jail Museum - BobaLew at the gallows! Best tour guide - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

Fun. Entertaining. Informative. Henry did a great gob with the tour. Highly recommend read more

The old jail museum was really cool. It gave a timeline of the jail system back then. It also had all the old stuff and relic guns. The tour was entertaining read more

Patrick was an awesome tour guide. Very knowledgeable and funny. Great with the kids.

This place was amazing! So much history was provided by our tour guide, Babalou. He was a great story teller; funny, engaging, switching voices according to the character he was recounting about and or the different rooms in the jail. We visited early in the morning, made the first tour group to go in. Both if my boys were very interested in the history and renained that way theougiut the tour. There is also a smaller museum, several gift shops and more information provided outside of the establishment. I highly encourage you to stop by. It's amazing how much one learns about the history we didn't know it was there through simply visits and yours if this such. read more

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DONT SKIP this tour! Thought was going to be a cheesy walk-through a cheaply made jail... well was I mistaken! "BENNY from the Bronx" gave us a great tour with plenty of facts. Very entertaining and FUNNY. Gave us a real idea of what it would have been for us had we been imprisoned there. Put us in the cells and closed the big iron doors which completely startled me and made it all seem more real. He took us through the whole place, including the isolation cell "hole"- which was completely insane. Benny was incredible; the knowledge on the sheriff was vast and we left there feeling as if it was still an active jail. Learned the real meaning of jailbird. Although fun and interesting you felt the sadness in that place. Thank-you, "BENNY FROM THE BRONX" :) read more

Took a tour of The Old Jail today. It was a better tour than I could have imagined. The guide was an excellent actor He stayed in character the entire tour. The history flowed . The tour went slow enough for me to imagine being stuck here. You should consider this a a destination while in St. Augustine. read more

Great tour and cool seeing the inside of the old jail along with hearing the history and stories of how prisoners were held. Our tour guide, "Jack the Ripper" was AWESOME!!! Great with the kids and amusing along the way. This helped to keep the kids attention and interaction high. Cool that the kids even got fingerprinted at the end of the tour. Jack even stuck around for some fun pictures. Glad we booked this tour and do recommend. Ask for Jack because I heard he is the best and I can definitely vouch for that!!! Make this part of your St. Augustine tour list!! Be sure to visit the gift shop also for some cool stuff. read more

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Coming down to St Augustine for a quick summer getaway, the old jail was #1 on our list of places to see and it did not disappoint. Great inmate tour guides made the experience absolutely authentic and interactive. We were lucky to explore the ins and outs of the jail with Bob Alew, who played harmonica as we were walking around the jail territory, shared stories of many notable inmates and threw in great jokes here and there. We love you Bob! read more

Old Jail Museum - Us and Bob - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

Boss Benny was great, informative and amazing. Very inclusive for everyone including my kids in some activities. they said thank you for the five dollar coupons that was really thoughtful and they got their ice cream. read more

During a weekend in St Augustine, we ended up visiting the jail twice. Once during the day during the regular jail hours and once during a nighttime ghost tour. The visit during the day was mediocre. Our guide was a little too corny in the way he told the stories so it detracted from the tour. The night visit was awesome! The guide really played his inmate part splendidly. He told the stories in a way that made them much more interesting and 'alive'. He positioned us in the jail so we could feel a sense of the times. The jail itself was very interesting. If you have any interest in that type of history then it's a good stop for your visit. read more

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Wow who knew watching Ghost Hunters would point me in the direction of a few of my favorite historical spots in St. A? So this Jail does have a pretty corny animatronic figure of the Sheriff, but the whole place is super fascinating. Its incredible to see how cramped, tiny and just plain horrible the cells are (but hey if you can't do the time .. don't do the crime, right?) but what is super interesting is the fact that the house the Sheriff lived in with his two daughters and wife is part of the building. The gallows are in their back yard. The tour guide was very informative and had plenty of stories to tell including one of a doctor doing studies on length of death after the initial fall in a hanging and how he had an inmate help him by wiggling his fingers if he was still alive. Which happened for up to 11 minutes after.. wow. So morbid. There is also a pretty complete gift shop of course. Again, kind of corny but get past that and relish learning more of the history of St. A. read more

Old Jail Museum - Jail in St. Auggie - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

I was a little skeptical to go on this Old Jail Museum tour, but my fiancee was very excited and completely for, so why not? (We also looked up some reviews, and saw that it wasn't a pretty bad tour, so again, why not?) I believe it was about $10 a person and you buy the tickets from a middle kiosk (right in front of the pink building - which is the jail, haha). The ticket kiosk has information on everything and the people inside are very friendly and had answers for all the questions we had. After we purchased our tickets, we asked where to go and he pointed us to this stand against the pink building. After waiting (the tours are about every 20-30min I believe) we were called up by the "jail trustees", aka the tour guides dressed as prisoners. We showed our tickets and the tour began. Our tour guide was Bucky and he was very enthusiastic about the tour (BE INTERACTIVE WITH THEM, OR IT'S AWKWARD FOR EVERYONE AND IT WON'T BE FUN!). Apparently I was put in jail because I was partying at the Ponce de Leon and hanging from the chandeliers by my ankles or something, totes a party animal, haha. We were led around the building to look at some things they used on the prisoners, then led inside to look at the Sheriff's home/jail. It was pretty interesting and there's a lot of information that I learned that I didn't know. There's great photographs inside and some neat artifacts inside as well. At the end you're allowed to walk around the upstairs and look around, good time to take some pictures if you hadn't been already. Some people are saying that this tour may have not been worth the price, but I believe it is because we came to view the city for it's history and help them keep the museum running, so I think $10 is a fair price to pay. I know I had a blast! read more

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Benny is the best, we have such a good time and the kids loved it! Make sure to do the museum next-door!

I would have normally not went to this attraction but our family wanted to go so I did. To my suprise I/We really enjoyed it. This was due to Bobalew our inmate tour guide who made it very enjoyable, informative and entertaining. Kudos and big shoutout to Bobalew. Perez/Donley Family read more

Ian was a great and entertaining tour guide! I thought it would be childish and geared towards children. However, it had a lot of insightful information about just how much the justice system has changed in just over the past 100 years. To be in the same jail cells as criminals once were really made me grateful that I was born in the 21st century next door is also the Florida history museum which is neat to spend 30 minutes walking through. read more

Old Jail Museum - Americas first fingerprint system - Landmarks & Historical Buildings Near Me - St. Augustine, Florida

Wow Boss Benny from Brooklyn just made this experience so memorable. We are with a field trip group with allapatah flats and 11am. He is super informative, fun, hilarious and great with the kids and adults. I think we got the best tour guide by far! Rockstar Benny thank you read more

I mean, it was mildly interesting. This isn't something I would put on my must see list. The gentleman giving us the tour was very nice, friendly and entertaining but there was nothing really outstanding about the history of this jail. Also, as a person of color, it was unsettling to see the pictures of black prisoners and a lynching tower out behind the jail. I know that not only Black people were lynched back in the day however it was still unsettling to see. But that's not a reason to avoid this tour. If you enjoy history then you might like this tour. Thankfully, the tickets were cheap. read more

Participated in the Old Jail tour on 24 June 2021. Our tour guide was Felix and he did an absolutely wonderful job. He was very knowledgeable and you could tell that he was very comfortable in front of a crowd. He interacted well with children and adults alike and was able to keep things light-hearted when needed. The tour information was very interesting and, even though some of it could have been graphic or gruesome, Felix was cognizant of the age differences in his audience and took that into account when presenting his information. The pricing of the tour was a little steep but the overall experience (due to the guide Felix) was worth it. I recommend taking the tour. Request Felix if you do; you won't be disappointed. read more