Arrested in Oldest Jail House St. Augustine Florida

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and Took the Best Vacation Selfies of My Life

I don’t usually spend my vacations in jail, but when I do… I make sure it’s haunted, historic, and full of photo ops.

Kevin and I were wandering through St. Augustine, Florida—a city that basically breathes history—when we found ourselves “locked up” at the Old Jail. And let me tell you, this isn’t just some dusty building with bars. It’s an experience. If you haven't read our St. Augustine Travel Guide yet then check it our here: A Non-beach Go-er's Adventure Travel Guide to St. Augustine, Florida

🗝️ Welcome to the Slammer

We signed up for a daytime tour and were greeted by a woman dressed in full prisoner garb—our tour guide. She didn’t just talk about the jail… she became the jailbird. Sass, sarcasm, and a lot of “you don’t wanna end up like me, kid” energy. It was hilarious and weirdly immersive. The whole thing felt like part improv show, part ghost-free ghost tour.

🚪 Inside the Cell Block

The tour took us through the old prison cells, where people were once crammed in without air conditioning (Florida heat, y’all…), and yes, they even recreated the hanging area outside. Super eerie, even in broad daylight. But also fascinating.

One of the creepier touches? Mannequins. Yup. They’re set up inside the warden’s living quarters, showing what daily life might have looked like. It’s supposed to be educational, but let’s be honest—it’s kind of creepy. Like Victorian dollhouse meets true crime documentary. Loved it.

📸 Prison Glam: Photo Ops You Need

I made Kevin snap a photo of me behind bars—because obviously. Then another one in the outdoor cage near the hanging area (a must for the Instagram grid, trust me). If you want to lean all the way into the jailhouse vibes, bring a striped shirt and commit to the bit.

Top Photo Tip:📍 Don’t skip the outdoor cage near the gallows—it’s weirdly the most photogenic part of the jail.

🕰️ A Quick History Break (Now With Extra Grit)

The Old Jail in St. Augustine was built in 1891—which makes it one of the oldest surviving jails in the United States. It was commissioned by none other than Henry Flagler, the Gilded Age industrialist and railroad magnate who basically shaped Florida’s east coast like a man playing SimCity.

Flagler wanted a jail that was far enough away from his swanky new hotel (now the Lightner Museum!) but still functional. So, naturally, he convinced the P.J. Pauley Jail Company out of St. Louis, Missouri (hey, hometown shoutout! 🙌) to build a jail that looked like a fancy Victorian house on the outside, but was all business inside.

And by “business,” I mean bare-bones cells, poor sanitation, and zero regard for human rights. The jail housed men and women—sometimes even children—and prisoners were used for labor during the day. Punishments were harsh, and public executions were a thing. The most haunting part? Some of the structures from that era, including the gallows, have been recreated on site to show what justice looked like in the early 1900s. Spoiler: it wasn’t cute.

The jail operated for over 60 years, finally closing in 1953, but not before it saw generations of inmates, extreme overcrowding, and the rise and fall of turn-of-the-century law enforcement. It was later transformed into a museum to preserve this chapter of St. Augustine’s complex (and kind of brutal) past.

🧠 Did You Know?

• The Old Jail was strategically built to blend in, so visitors wouldn’t be scared off by a spooky prison while visiting Flagler’s luxury hotels.

• The jail’s builder, P.J. Pauley Co., also constructed other notorious prisons—so, they were kind of the HGTV of creepy lockups.

• Some claim it’s haunted (though no official ghost tour is run here)… but let’s be real, any place with gallows and mannequins probably has some spooky energy lingering.

💡 What You Need to Know Before You Go

• 📅 We visited in May and the weather was perfect—warm but breezy, and way fewer crowds than peak summer.

• ☀️ Summer gets packed, so book your tickets ahead of time. This place is close to the beach, so it pulls in a lot of tourists.

• 🎟️ Tours sell out, especially if you’re bundling with other local attractions (hot tip: combo tickets are cheaper).

• 📸 Bring your camera or a fully charged phone—between the mannequins and the iron bars, you’re getting some weirdly aesthetic shots.

• ⏰ Plan for about an hour, unless you're deep-diving into every display plaque (no judgment if you are).

🧳 Final Thoughts

I wouldn’t say going to jail was the highlight of our St. Augustine trip… but it’s definitely one of the most memorable stops. It’s quirky, historical, a little creepy, and honestly? Just a ton of fun.

So if you’re wandering through the nation’s oldest city and looking for something offbeat but educational (with bonus Instagram points), get yourself arrested. Just make sure you’re out in time for tacos.

Want to bundle this with a visit to the Castillo de San Marcos or Pirate Museum next? Stay tuned—those stories are coming soon, and they involve cannons, ghosts, and at least one parrot.

👇 Drop a comment if you’ve done the Old Jail Tour—or if you’ve got a weird historical site you think I should check out next!