Saint Augustine: Private 1920s Tour in Vintage Car for 4

Summary

Private vintage car tour with costumed guides & real stories

You’ll climb into a quirky vintage car with your own private group, led by a guide dressed straight out of the 1920s. Expect waves from strangers, real stories behind Saint Augustine’s oldest streets, and time to soak up the sounds and smells of America’s oldest city — all at your own pace. You might even end up in someone else’s vacation photos.

What’s the experience like?

We piled into this old-fashioned car right on the edge of Saint Augustine’s historic district — honestly, I felt a little ridiculous at first, but our guide (her name was June) just grinned and tipped her hat like she’d done it forever. The city looked different from that low rumble of wheels, and people actually waved as we passed. One kid pointed and shouted something about “movie stars.” I guess you sort of become part of the scenery here.

June knew every crack in the cobblestones and half the folks we rolled past. She’d slow down near these weathered stone gates or Spanish balconies, tossing out stories about pirates or old hauntings — sometimes she’d pause mid-sentence if someone yelled hello from a porch. There was this moment by the old fort where she stopped, let us listen to the gulls and distant church bells, then told us how her grandfather used to sneak out fishing before dawn. It smelled faintly of salt and sunscreen, even though it wasn’t hot yet.

I tried asking about some street name in my best attempt at Spanish — June laughed so hard she nearly missed a turn. She said locals still argue about pronunciations here; I believed her. The whole ride felt less like a tour and more like tagging along with someone who loves their city enough to dress up for it. We got our picture taken by strangers at least three times (I’m not sure what they’ll do with those photos). Anyway, I still think about that stretch along Aviles Street where everything seemed both new and impossibly old at once.

Step-by-step itinerary

Day 1 — Guided historical tour of Saint Augustine

• Meet guide in 1920s attire
• Ride unique vintage vehicle
• Visit historical city sites
• Hear stories behind landmarks
• Take photos and wave to travelers

Top questions

How many people can join this private Saint Augustine tour?

The private historical tour is for groups of up to 4 travelers.

Is pickup included for this Saint Augustine vintage car tour?

Yes, private transportation is included for your group.

Are service animals allowed on this historical tour?

Yes, service animals are allowed during the tour.

Is this tour suitable for all fitness levels?

Yes, it's suitable for all physical fitness levels since you'll be riding throughout.

Can infants join the Saint Augustine private tour?

Infants can join but must sit on an adult's lap during the ride.

What’s included

Your day includes private transportation around Saint Augustine for your group of up to four travelers, with a local guide dressed in full 1920s fashion sharing stories along the route — just hop in and enjoy being part of the city’s living history while others wave you by.