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The Authentic Old Jail


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The Authentic Old Jail


Home to prisoners for over 60 years, the Old Jail in St. Augustine looks more like a resort than a maximum-security facility. The original structure was built in 1891 by Henry Flagler, and although it has been restored and renovated throughout the years, it looks very much the way it did when it opened over a century ago.

Today, visitors to the Old Jail can take a guided tour, learn about the many prisoners and practices that took place here and see where the Sheriff and his wife and family lived— adjacent to where the prisoners were housed.Meet Sheriff Joe Perry who had a reputation as being a harsh and strict warden – one of the toughest in the South. Walk through the men's and women's cells and see where executions took place in the gallows. Discover the history behind judicial practices in the 19th century and see an array of weapons and artifacts.

Adults and children are thoroughly entertained by our costumed actors who portray deputies from the early days and everyone gets a chance to try and escape! The Old Jail is one of just a few prisons of its kind still standing and makes for a great sightseeing and history adventure.

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What Guests are Saying About the Authentic Old Jail


Great tour!

We all had a great time on this hop on hop off tour. St. Augustine is a very charming town full of many activities from sightseeing to shopping to eating some amazing foods. We thoroughly enjoyed the St Augustine Distillery! We took the tour and afterwards we got to sample some of their products! We ended up buying the St. Augustine Mule mix!
Love this Tour...

Our first visit in this beautiful town and this Tour is definitely a great help, it gives you a brief history of all the tourist sites is very informative, it is a complete tour of the major attractions, I highly recommend it. We missed many things to know, This Tour offers many options that fit every need even the same ticket serves for 2 days, it is very good, I hope to return soon.
Oz is the Greatest!!!

No! Not the Wizard of Oz and not Dr. Oz either! I mean the one, the only, Oz the Great of St. Augustine! We stayed on his train for the entire tour of St. Augustine. We learned so much about the city, special points of interest, and where we wanted to visit. It was great!!!

Best way around...

Everyone from tickets to drivers were wonderful. The route has many stops and pickup locations. The trolley drivers were very knowledgeable of the area. Since parking downtown is expensive, the trolley is the best and easiest way to see the area.
Great time!

We had our 14 yr old and our 4 yr old with us. There is so much to do and to see and the Old Town Trolley makes sightseeing fun and enjoyable for all ages. The depth of history given on the tour is amazing. We already loved St Augustine but we adore it even more now. Our favorite driver was Bud!

Worth every penny.

When you add up parking fees, admission fees and just generally the pain of finding good parking the trolley is worth every penny. Our favorite drivers were Mr Capital and Greg. Both seemed to have more cool facts.


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Authentic Old Jail - St. Augustine, FL
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Authentic Old Jail - St. Augustine, FL
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Authentic Old Jail - St. Augustine, FL
Image may be subject to copyright
Authentic Old Jail - St. Augustine, FL
Image may be subject to copyright
Authentic Old Jail - St. Augustine, FL
Image may be subject to copyright
Authentic Old Jail - St. Augustine, FL
Image may be subject to copyright
Authentic Old Jail - St. Augustine, FL
Authentic Old Jail - St. Augustine, FL
Image may be subject to copyright
Authentic Old Jail - St. Augustine, FL
Image may be subject to copyright
Authentic Old Jail - St. Augustine, FL