St. Augustine’s Old Jail

It’s a whole new kind of put-prisoners-to-work program… The Old Jail in St. Augustine has prisoners from the 1890’s keeping the grounds, guiding tours and even entertaining the kids!

Our family headed to The Old Jail last weekend to check out this local attraction.  At first, Georgia Anne (4) was afraid to go to jail… by the time we left, she was begging to go back!!  Hopefully she outgrows that…

When you arrive to the Old Jail part of the Old Town Trolley complex, a clock shows what time the next tour will start.  You’ll likely have plenty of time to walk through the giftshop & visit the restroom.  On rainy days you can go into the History Museum {free} for a crash course in St. Augustine’s history.

We were with our littles, so we stayed outside.  While we waited, a “prisoner” handed out honorary badges to all the little cops & robbers.

Protip: While you wait for your Old Jail Tour or for the next Trolley to roll up, walk around the right side of the jail and find hopscotch, horse saddle and fun photo ops to keep the kids busy!  My kids liked the “birdcage” jail cell- there are also stocks and a sherriff/prisoner painting you can stick your face through for funny pictures.

Your guide will share the “arresting” history of Henry Flagler’s involvement in the Old Jail’s location and architecture.  Constructed in 1891, it was pink long before Arizona Sherriff Joe made prisoners wear pink!

Inside, we walked through female cells first and then maximum security cells.  Georgia Anne didn’t think it was so bad until she learned inmates had to pee in these small buckets.

“And poop!?!” she asked.  “In front of everyone?”

Yes, Georgia.  That, too.  Being a bad guy is a bad idea!

Our tour took us through the kitchen, where women prisoners would prepare whatever the men wanted for breakfast… as long as that was grits.  The guide’s dry humor was lost on the kids when she said that- that’s how we do meals at home, too!  I offer two options at every meal- eat or don’t! 😉

The Sherriff’s quarters, by contrast, were quite plush for 1891!  We breezed in and out- I’d love to go back and look at the room with the kids when we can compare & contrast life then to now.  Lighting was provided by the kerosene lamp on the table & gas fixtures from the ceiling.  Time was passed with a basket of yarn & knitting needles, not a Wii or computer.  Meals were served on fine china and mail all came through the Sherriff’s office!

Upstairs, there was plenty of time to casually explore the cells…

…and see real implements used here at the jail.  Ben was especially interested in all these weapons confiscated from inmates over the years- from ice picks to pistols to forks & knives and monkey knots made of rope.

After we read articles, explored artifacts and felt what it was like to share a teeny cell with 3 other inmates, we accepted our pardon and headed outside past the gallows to take silly pictures.  A trip to St. Augustine isn’t complete for our family without a silly “let’s play tourist” moment!

When you visit, share your silly pictures with me on the Simply St.Augustine Facebook page!

The Old Jail
167 San Marco Ave
Adults $9 ish, children 6-12 years $5 ish

Our family entered the Old Jail free as part of a “hometown pass” month they offered St. John’s County residents.  To hear about specials for locals, subscribe to my email list & I’ll keep you in the loop!!


  1. Teresa says

    The first time I ever stepped foot in St. Augustine I was 4 (so we’re talking 1966). I remember walking down the street and just begging to go over to the jail and fort. My father and mother wouldn’t have it. Said I was too young to see such stuff. LOL It’s funny that that is all I can remember from that trip. We did a “tour” of different towns in Florida that year. My father was a Presbyterian minister and he lined up several churches to preach at to pay for the trip. We were in Florida for 3 weeks. St. Augustine, Lakeland, and Sarasota. One of the good memories from my childhood.

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