St Augustine: Trolley Pass & Old Jail, Museums Entry

Summary

Hop on the trolley, meet locals in costume, and time travel through St Augustine’s past

You’ll wander through St Augustine’s storied streets by trolley, step into history at the Old Jail (with actors who don’t hold back), and poke around quirky museums filled with oddball treasures. With included entry tickets and hop-on hop-off freedom, you’ll catch moments that stick with you—sometimes in unexpected ways.

What’s the experience like?

It started with a laugh at the Old Jail—one of those real, belly-deep laughs you only get when you’re caught off guard. The guide (I think his name was Tom?) clanked a set of old keys and hollered something about “fresh meat.” I didn’t expect to be “locked up” for a photo, but there I was, behind bars with my friend pretending to plead for mercy while Tom grinned like he’d done this a thousand times. The place still smells faintly of iron and old wood, even after all these years. Kids in our group were wide-eyed; honestly, so was I.

After we escaped jail (with our dignity mostly intact), we hopped onto the Old Town Trolley. The driver had this easy way of pointing out things I’d never have noticed—like how the Spanish moss hangs differently near the city gates or which stop has the best ice cream (he swore by Stop 4a). The breeze from the open sides felt good, especially since Florida sun is no joke. We could get off anywhere along the 21 stops, but ended up lingering at the History Museum longer than planned. There’s something about seeing old maps and letters up close—makes you realize how many hands have shaped St Augustine.

The Oldest Store Museum was next. It’s packed with stuff I’d never even heard of—a goat-powered washing machine? Seriously? Our guide there wore an apron and kept tossing questions at us (“Guess what this tonic cured!”), and Li laughed when I tried to say “elixir” in Spanish—probably butchered it. The shelves creaked under jars and gadgets that looked like they belonged in a movie set. It smelled like dust and cinnamon oil; someone must’ve spilled something near the counter.

By late afternoon we were back on the trolley, feet tired but not ready to call it quits. There’s something comforting about riding past centuries-old churches and hearing snippets of stories from other travelers or locals just going about their day. I still think about that view from Stop 5b—the Castillo de San Marcos glowing in late sun—and how everyone got quiet for a second as we passed by. Not everything needs words, you know?

Step-by-step itinerary

Day 1 — Explore St Augustine historic sites

• Take Old Town hop-on hop-off trolley
• Visit Old Jail with actors
• Explore St Augustine History Museum
• Experience Oldest Store Museum

Top questions

Is hotel pickup included with this St Augustine attractions pass?

No, hotel pickup isn’t included. You can start at any trolley stop or museum listed on your pass.

How many stops are on the St Augustine hop-on hop-off trolley tour?

The trolley tour has 21 stops throughout St Augustine.

Are admissions to museums included in this pass?

Yes, admission to the Old Jail, St Augustine History Museum, and Oldest Store Museum are all included.

Is this tour wheelchair accessible?

The museums’ lower floors are wheelchair accessible; check locally for full details.

Do I need to reserve a spot ahead of time?

No reservations are required for this attractions pass—it’s flexible.

Can infants or small children join this tour?

Yes, infants and small children can ride in prams or strollers on this tour.

Does this run in bad weather?

Yes, it operates rain or shine—just dress appropriately for Florida weather.

Are service animals allowed?

Service animals are welcome on both the trolley and in museums.

What’s included

Your day includes unlimited rides on the hop-on hop-off St Augustine trolley plus entry tickets to three main attractions: the Old Jail (complete with costumed guides), St Augustine History Museum, and Oldest Store Museum Experience—all without needing reservations or extra fees along the way.