Saint Augustine:
The Oldest City
in America.
Spanish forts. Cobblestone streets. Ghost tours.
Founded in 1565 — 42 years before Jamestown. Just two hours from Orlando, it feels like stepping into colonial Spain on American soil. Here's how to make the most of it.
The Backstory
Where American history began — 42 years before Virginia.
Most people learn that the United States was founded by the English in 1607 at Jamestown, Virginia. Not quite. The Spanish got here first — and in 1565 they founded St. Augustine on Florida's northeast coast.
More than 400 years later, Saint Augustine is still the oldest continuously inhabited European-founded city in the United States. It's living history: preserved Spanish colonial architecture, intact 17th-century forts, cobblestone streets, and the Spanish flag still flying in several places.
The atmosphere is the complete opposite of Orlando. You feel like you've crossed the Atlantic — authentic European architecture, romantic for couples, nighttime ghost tours steeped in 400 years of legend, and genuine Spanish cuisine. And it's all just two hours away. A single day works, but one or two nights is better.
What to See
The must-see attractions
From the oldest fort in the country to Tiffany stained glass and haunted streets.
Castillo de San Marcos
$15 adult · 2 hours · kids free
Built between 1672 and 1695, the oldest masonry fort in the U.S. — original walls and cannons, a preserved inner courtyard, Spanish soldiers' quarters, and panoramic bay views. Weekend reenactments feature period uniforms and cannon fire. Unmissable.
Flagler College
$12-15 tour · 1 hour
Built in 1888 by Henry Flagler as the most luxurious hotel of its time, now a private college that opens for tours. Spectacular Moorish-Renaissance architecture, the world's largest in-situ collection of original Tiffany stained glass, and a dining hall with 120 Tiffany windows.
St. George Street
Pedestrian-only · shops & dining
A historic pedestrian street lined with shops, restaurants, crafts, and bars in an authentic Spanish atmosphere. Grab local datil pepper jelly, handmade Spanish jewelry, and dine at the iconic Columbia Restaurant (Spanish-Cuban, est. 1905).
Ghost Tours
$25-35 per person · evenings
With 400 years of history, urban legends spill onto every street. Costumed guides lead nighttime walks past 'haunted' sites. Try A Ghostly Experience Walking Tour, Ghosts & Gravestones trolley, or the Original Haunted Pub Tour. Great for couples and families with teens.
Bridge of Lions: a 1927 bridge guarded by two marble lions, connecting the historic district to Anastasia Island. Unmissable for sunset photos.
Old Town Trolley Tours: a hop-on / hop-off trolley with 22 stops ($35-40 adult). Ideal for a first visit, especially with families.
St. Augustine Lighthouse: an 1874 historic lighthouse — climb 219 steps for a 360° view of the ocean and city ($17 adult). A photographer's favorite.
Plan Your Trip
Optimized itineraries
1 Day (Day Trip)
- 7:00 AMLeave Orlando
- 9:00 AMArrive in Saint Augustine
- 9:30 AMCastillo de San Marcos (2h)
- 11:30 AMWalk St. George Street
- 12:30 PMLunch at Columbia Restaurant
- 2:00 PMFlagler College tour (1h)
- 3:30 PMTrolley tour or Lighthouse
- 6:30 PMBridge of Lions at sunset (photo)
- 7:30 PMDinner at a historic restaurant
- 9:00 PMDrive back to Orlando
Tiring, but doable.
2 Days (Recommended)
Day 1
- Castillo de San Marcos
- St. George Street + shopping
- Flagler College
- Lighthouse at sunset
- Premium dinner
- Nighttime Ghost Tour (don't skip it)
Day 2
- Breakfast at a historic bakery
- Trolley tour
- Anastasia State Park (beach)
- Drive back to Orlando
Historic inns: Casa Monica Resort & Spa (luxury), St. Francis Inn (1791 B&B), Cedar House Inn (romantic), Westcott House (ocean view). Roughly $150-400/night.
Where to Eat
Restaurants worth the stop
The Columbia's legendary "1905 Salad" and authentic paella are local institutions.
Know Before You Go
Practical tips
Arrive Early
The Castillo de San Marcos opens at 8:45 AM. Go early to beat the crowds.
Parking
Downtown has paid lots ($3-5/hour). Cheaper: free parking at the Visitor Information Center plus a 15-minute walk.
Comfortable Shoes
Cobblestone streets are unforgiving — skip the heels and thin sneakers.
Sunset Photo
The Bridge of Lions at sunset is the must-have shot. Arrive around 6:30 PM for perfect light.
Halloween Season
October is the best month — themed decor, ramped-up ghost tours, and cooler weather.
Buy Datil Pepper Jelly
A unique local specialty and an authentic souvenir you won't find elsewhere.
Getting there from Orlando
Address (historic district): 75 King Street, St. Augustine, FL 32084
Drive time: about 2 hours via I-95 North
Route: I-4 East to I-95 North, take Exit 318 (King Street), then follow signs to downtown St. Augustine.
Tolls: roughly $5 round trip (I-4 Express, optional).
The GS Difference
Arrive in style. No fine print.
Some visitors spend their whole lives coming to Orlando and never discover Saint Augustine. That's a big miss. After eight days in theme parks, two days in Saint Augustine reset everything — colonial architecture, living history, a European atmosphere on American soil, authentic Spanish food, ghost tours after dark, and sunset over the Bridge of Lions.
GS Car Rental is built for exactly this kind of road trip: maps and tips for the drive, recommendations for historic inns, friendly support, no hidden fees, and free airport delivery (MCO, MIA, FLL, SFB). For couples, the Mustang Convertible, Cadillac Lyriq, or Tesla Model Y; for families, the Sienna, Pacifica, or Tucson.
FAQ