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

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

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

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

Had a great time from beginning to end! Met Benny, our tour guide, who was very funny and informational. He involved everyone in the group which made the tour very enjoyable. Our kids had a blast! Would highly recommend. I would definitely recommend to get there early as the parking lot fills pretty quickly. We got there at 9. read more

Super cool! This was my boyfriends favorite part of the whole trip. Our tour guide "Bobalew" make our experience absolutely AMAZING ! He has such a great personality and made my birthday trip the best tour we had. He was so funny and very intelligent with his information ! Great tour 10/10 would recommend! read more

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We rode the trolley by the Old Jail last year on our family vacation and didn't have time to go. When we decided to go to St. Augustine again, my 8 year old son was adamant that we go to the Old Jail this year. I was worried the anticipation would be be more exciting than the actual tour - but it was great! Our guide had a great sense of humor and interacted with our entire family. I always ask my son if he had a thumbs up or thumbs down time and his thumb immediately shot up on this one! read more

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

Bobalew is a true entertainer! Definitely do the tour with him! I normally avoid tourist traps but this is not one of them; small but full of history. read more

I really enjoyed my experience at the old jail. We had been previously but our tour guide was so good and just made the whole thing 100%. He knew the answers to every question and could tell he really knew the history. He was witty and just made the whole thing fun! I wish I remembered his name but he had red hair. Please stop by here! read more

We loved this museum! My teen who isn't amused easily thought he was being arrested lol Boss Benny was the best "inmate". Thoroughly entertaining and Benny is quite the singer! Worth the time and money! read more

Great tour. Guide kept it all interesting and involved the group. Would recommend as a must stop.

Very interesting to hear about this old Jail. Enjoyed the tour, which took about 30 minutes. Then they let you wander around on your own and take pictures. The stories they tell are pretty shocking. read more

Prison trustee Harrison was fantastic. Coming from a local, he was one of the best tour guides I've ever encountered. He was very informative and answered all of our questions with confidence. He made the whole experience a blast and we are looking forward to coming back soon! read more

What an informative and fun tour this was!! I highly recommend it. Very interesting and surprising stories to which I wad unaware. Ask for Deputy Otis as he knows that jail inside and out! read more

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

I am currently visiting from Missouri, and we acquired tickets to visit the old jail in a package deal with our trolley tour. Even though I may not have bought the tickets otherwise, I ended up really enjoying this tour. The staff was dressed up and in character, which added to the experience. The tour was about 30 minutes long, and very educational. I really enjoyed our guide, whom I believe was named Frank. He was a fun character that was very interactive. This is a great quick stop on your vacation! read more

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

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This could have been an okay tour, but we bailed after the first room. The humor was just not for us. If you want to hear about the poop habits of prisoners incessantly, then this might be the tour for you. Let me sum it up for you...it's an old jail, the conditions sucked, they had beans for lunch and dinner with no seasoning, and grits with no butter or cheese for breakfast, and they have recorded 8 (count 'em...8) hangings in its history (not that there weren't more, they just supposedly weren't documented). I don't understand the glowing reviews of this attraction... to me, it was a negative 10, but that rating isn't allowed. I'd skip it... read more

Took the family on our annual Saint Augustine trip and visiting this museum. Worth visiting for sure. Tour guide was funny too.

Excellent and worth every bit of ten dollars. Pay it. If you want to experience what it was like to be in jail back in the day, visit this place. I would have never made it. The actors are all in costume and act the part. Our actor (Bucky) was excellent. Nice job Bucky. read more

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This was a fun tour. Edith was an amazing tour guide and very knowledgeable. Would recommend to anyone looking for something to do.

What a trip! Our tour guides, Inmate Mildred and Molly at the old store, really made this trip special. They were excellent tour guides and very fun and interactive! read more

During our trip to St. Augustine last week, my wife and I visited the Old Jail Museum (Monday March 29). Jasper was our guide and he was excellent! The sections within the museum did get crowded. However, if you're not as concerned about getting COVID (as more people are getting vaccinated and/or the whole herd immunity thing), you'll enjoy your time here. read more

We had the best time! It was totally affordable and a fun excursion for an hour or two. Our tour guide was jack who was so much fun and kept things so interesting. We were laughing the entire way through. Thank you for the best time, Jack read more

St Augustine is a highly walkable city if you are in reasonable health, but parking for those not staying in one of the hotels located in the historic district can be tough. It is for this reason we decided to purchase a tour with Old Town Trolley. Parking at their main pick-up on San Marco Avenue is free and there stops included ALL the places we wanted to see while visiting this 450 year old city! Also included with your ticket is admittance to St. Augustine History Museum (meh) and discounted tickets to the Old St. Johns County Jail Museum. Now, I was totally against this, but I was overruled by the head hen in our house and those two offspring chicklets of mine. Oh I puffed out my chest and tried to insert my rooster masculinity in protest, but she bought the tickets anyway. LOL THE EXPERIENCE Tours are given roughly every 20 minutes and begin at the front entrance. Here someone will be dressed in period clothing as either the prison staff or the prisoner themselves. You are officially being "taken into custody" during the tour and will need to pick up a pardon of release form upon exiting. During the tour you get to see all parts of this old jail built in 1891 by Henry Flagler, one of the richest men of his time and responsible for a great deal of the growth of the city. Flagler was building all kinds of things including luxury hotels for the super-rich and did not want the local government to build a jail "in town". So adamant was he that he gave the city $10,000 to build it a mile outside of town. He also demanded it not look like a jail, which is why it has a porch and regular windows on the half of the building facing the town. The tour takes you through the lower jail where the kitchen, maximum security cells (for those condemned to die) and women's cells are located. Just past the kitchen you will visit the prison offices and living quarters for the sheriff. Next you will walk through the upper jail which was for general population and looks a lot like a warehouse with a double deck metal cage in the center. Displays of weapons used in crimes of the day are on display as well as old photos. Outside are the hanging gallows for more serious crimes and various other forms of punishment designed for public humiliation such as cages, stocks and pillories. There is also a railroad car designed to house prisoners who were used as free labor on the rail system. Lots of fun photo opportunities here. NOTE: This jail was built by the same company responsible for building Alcatraz. FINAL THOUGHTS The tour itself is just okay, but it was more interesting than I thought it would be. read more

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Our guide Patrick was great and informative. He made us laugh . Very interesting place, we visited on July1, 2023 and throughly enjoyed and was educated on the jail conditions that existed in the past. read more

The museum was good, their is a line which they call 8-12 people at a time every 20 minutes. The people are very informative and friendly, it was a pleasant museum as it very small and not much to see. read more

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We actually live not too far but for some reason never go to this historic and touristy Old Jail. But at my son's request we dropped by today while in town. It is really pretty cool and if you also go through the museum on the left that is adjacent the gift shop and snack bar it is a double plus. If you like history, Florida history then do stop by. read more

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Jack At The Old Jail! Oh. My. Gosh. He Was Amazing!!! Couldn't Have Had A Better Tour Guide. Had Us Laughing Our Butts Off!!! After The Tour He Even Pulled Some Of Aside And Told Us Some Spooky Ghost Stories! Which Made Us Super Excited For Our After Dark Experience! Overall Jack Is Amazing At What He Does! Thank You For Giving Us An Even Better Honeymoon!!! read more

This won't show you 16th century Spanish prison conditions. Just late 1800s. Doesn't need to be a guided tour. Interesting building, and it's interesting to see how cramped and in humane the cells were. Beyond that, it's not that interesting. Our tour guide Buckey was rude, condescending and not funny. The gag is to treat you like you're a prisoner but he was abrasive and patronizing and seriously unfunny. Did not enjoy him at all. read more

A wonderful addition to our vacation, the Jail Museum was great for all ages. It featured authentic and engaging exhibits. Bobalew got right into character and was a great tour guide. Ask for Bobalew; he's the BEST! read more

Here is the best advice I can give you, and that no one else has bothered to mention to you: GET THERE EARLY! My friend and I got there at 10:30 and already, the parking lot was packed! They open before 9, so be one of the first people there, or spend a good 30 minutes or more circling the lot to find a place to park. You're welcome. The old jail is probably nothing like what you'd expect a jail to look like -- it's pretty, it's pink, and looks inviting. There are trees hanging with Spanish moss even. In fact, according to our tour guide, Henry Flagler was forced to build the jail in that aesthetically pleasing Romanesque Revival fashion, and once he did, snowbirds and other tourists confused it with a hotel, asking to be checked in upon arrival to the city! The jail was functional until 1953, and now, it is used solely as an attraction. It contains two stories, and housed both male and female prisoners. The sheriff lived on site, and had his own dwelling on the second floor, with his office in the first floor. Prisoners had to cook and operate the kitchen, among other chores, such as day labor, and bringing in food. A total of 8 men were hung from the gallows during its history. Some of the prisoners on the first floor were privileged enough to have a window in their cell -- or so you'd think -- until you see for yourself what their view was: the operating gallows. Not much of a relaxing view, is it? Men and women were housed in this jail and the conditions were so poor that they'd only be allowed one bath a month, and they'd all bathe in each other's water. You can imagine how unsanitary that'd get, especially if that person was hygienically challenged! This is probably why disease was so rampant. Segregation was also practiced here. On the tour, you're able to see the firearms and weapons that were confiscated on site from the prisoners, and walk into the cells themselves, to experience a few minutes inside a jail cell. The solitary confinement area is quite dark, cramped, and creepy. Supposedly, the jail is said to be haunted, so keep an eye out for a ghost, whether in your pictures, or grazing past your shoulder. read more

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Our guide was Bobalew - so much fun. Glad he only kept us there for there days. Pay attention and ask questions - they know so much and are just fun people. Go to the history museum too. read more

It is a tradition to visit St Augustine every year for their night of lights. I always feel at home in this city though I am not a resident. It was a bit unsettling the first time I visited the Old Jail. St. Augustine was not always the warm and inviting city it is now. The city is rich in history, but I often forget the dark underbelly. It Is pretty disturbing to find out how the poorest were treated back in the day. I doubt it is the inmates who haunt this old jail like the ghost tour claims. It would probably be the despicable sheriff who ran it. read more

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

Of all the historic Activia to do in St. Augustine, this is my families favorite. The guided tour is a fun historic experience. The tour guides are informative and fun. They do have a few peyote spots sey up around the jail. They do have military discount. read more

Was looking forward to visiting this historic sight for some time and was so pleased! Sure, the actor was cheesey but she gave us some cool facts about the jail. Once her presentation was done though we got to go off by oursleves. The place is really cool, you can really feel the heaviness of the place just standing quietly in a cell. The Cells were tiny and cramped, the bars are solid iron, the walls and ceiling are cement. They have the one and only picture of a hanging, which is very eerie and though the tour was a quick one it is one I'll always remember. A sure Must Do in St Augustine. read more

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Patrick was fantastic! Not gonna lie; I wasn't too excited for the jail house, but my girlfriend was so excited. Historically interesting, but the experience was made all the better by Patrick. Loved the jokes, loved the banter, loved the info. 10/5 Patrick read more

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

Loved our visit to the Jail museum. Our guide was Bobalew, and he did a fantastic job of telling us the history. Hope he gets a pardon soon. read more

Old Jail Museum is one of the few sights I actually paid money to get a tour in St. Augustine. Unlike other sights in St. Augustine, this place has a free parking, since it is a bit outside of downtown. We took the last tour of the day at 4:30pm. It was just me, my husband and 4 other people. The tour lasted about 20 min. I kinda felt like $10 is bit too expensive but nonetheless, this place was unique. read more

Best tour hands down!!!! I'm only disappointed that I didn't book the after dark version!!!! Lots of history and our guide Benny was the best! read more