St. Augustine, Florida - “America’s Oldest City”

3-Hour Private Driving Tour

America’s Oldest City, Five centuries of history, seen the easy way.

St. Augustine isn’t just old—it’s layered.

This 3-hour private driving tour is a relaxed, story-driven way to experience America’s oldest continuously occupied European-founded city, without rushing, crowds, or information overload. We connect forts, neighborhoods, coastlines, and colonial streets into one clear story—Spanish, British, American, and everything in between.

Comfortable driving. Short walks. Real history that actually makes sense.

What This Tour Is Like

Think Old World history with a coastal Florida breeze.

We move at an easy pace, stopping where it matters, skipping what doesn’t, and explaining how St. Augustine became what it is today—from 16th-century Spanish outpost to modern coastal town.

Always private. Always flexible.

The Places We Explore

This tour is built around ten specific locations that anchor St. Augustine’s story. Order may vary slightly based on traffic and interests.

Castillo de San Marcos
The heart of the city. We start with Spain’s massive stone fortress and explain why St. Augustine survived when other colonies failed.

St. George Street
A slow drive and short walk through the colonial core—street life, trade, and daily routines across centuries.

Plaza de la Constitución
The city’s civic center since the 1500s, connecting government, church, and public life.

Cathedral Basilica of St. Augustine
The oldest Catholic parish in the U.S.—faith, power, and empire in one place.

Lincolnville Historic District
A Reconstruction-era neighborhood founded by formerly enslaved people, central to St. Augustine’s Black history and Civil Rights story.

Flagler College
Gilded Age ambition, Henry Flagler, and how tourism reshaped the city in the late 19th century.

St. Augustine Lighthouse & Maritime Hamlet
Navigation, shipwrecks, and coastal life—how people arrived, survived, and sometimes didn’t.

Fort Matanzas National Monument
A quiet but crucial Spanish fort guarding the southern approach—showing how defense worked beyond the main city walls.

Anastasia Island
Coquina stone quarries, barrier island life, and the materials that literally built St. Augustine.

Bridge of Lions
We wrap up with views that tie everything together—old city, new city, water, and movement.

What We Focus On

Spanish colonial history

British and American transitions

Forts and coastal defense

Reconstruction and Civil Rights

Tourism, preservation, and reinvention

This is real St. Augustine, not a theme park version.

Tour Details

Duration: 3 hours

Format: Private driving tour

Group Size: Your group only

Walking: Light and optional

Pace: Relaxed and flexible

Who This Tour Is For

First-time St. Augustine visitors

History lovers who want clarity, not lectures

Couples, families, and small groups

Travelers who want to see more with less stress

Why Back Porch Tours

We don’t rush you through history.
We connect the dots, tell good stories, and let the city do the rest.

It’s like seeing St. Augustine with a local who knows where to drive—and when to slow down.

Booking Notes

Private tour · advance booking recommended

Route may adjust for traffic or weather

Pairs well with Florida collection tours