Ocala to St. Augustine: Complete Travel Guide
America's Oldest City — Colonial Forts, Flagler's Gilded Age & Atlantic Beaches
About St. Augustine
St. Augustine holds a unique place in American history: founded in 1565 by Spanish explorer Pedro Menéndez de Avilés, it is the oldest continuously occupied European settlement in the United States — older than the Pilgrims landing at Plymouth by 55 years. Today, the Historic District preserves that history in stunning physical form: the Castillo de San Marcos fort, the old Spanish quarter streets, and Henry Flagler's extraordinary Gilded Age hotels now serve as college buildings and museums.
From Ocala, St. Augustine is a 100-mile drive northeast via I-75 to I-10 to US-1, or the more direct SR-40 to I-95 North route. The city rewards slow exploration — walking the narrow streets of the Historic District, climbing the Castillo's ramparts over Matanzas Bay, and settling in at a rooftop bar for a sunset view. St. Augustine Beach, just minutes from the historic core, adds Atlantic Ocean access to an already remarkable destination.
Getting from Ocala to St. Augustine
Primary — SR-40 E to I-95 N
SR-40 East to I-95 North; Exit 318 (SR-16) into St. Augustine
Alternate — I-75 N to I-10 E to US-1 S
I-75 North, I-10 East, then US-1 South into St. Augustine
Parking Tips
Historic District: use the St. Augustine Visitor Information Center parking garage (San Marco Ave) — free first hour, then nominal fee. The Castillo de San Marcos has limited lot parking. Lincolnville and San Marco Ave street parking: free. St. Augustine Beach: free municipal lots. The Old Town Trolley hop-on/hop-off ticket includes parking at the Visitor Center.
Best Time to Visit St. Augustine
65–82°F, comfortable humidity
Excellent weather for walking the historic district. Spring break brings crowds; shoulder season (April–May) is ideal.
88–94°F, very humid
Beach season at St. Augustine Beach. Historic district can be hot; visit museums and shaded areas midday.
72–85°F, improving
Best months to visit. Nights of Lights preparation begins November. St. Augustine Pirate Gathering (October) is excellent.
48–65°F, occasionally cold
Nights of Lights (Nov–Jan) is one of Florida's most magical seasonal events. Smaller crowds except holiday weekends.
St. Augustine Neighborhoods Guide
Historic District
Cobblestone streets, colonial architecture, and centuries of layered history
- ·Castillo de San Marcos
- ·St. George Street pedestrian shopping
- ·Spanish colonial buildings and museums
Lincolnville
African-American historic neighborhood with Victorian homes and local character
- ·Civil rights history (MLK visited 1964)
- ·Victorian architecture and B&Bs
- ·Local restaurants away from tourist prices
Uptown St. Augustine
Historic Flagler College and transition neighborhood between downtown and residential
- ·Flagler College (former Ponce de León Hotel)
- ·Villa Zorayda Museum
- ·Local coffee shops
Vilano Beach
Small Atlantic beach community just north of the inlet, less developed than St. Augustine Beach
- ·Quieter Atlantic beach access
- ·Local seafood restaurants
- ·Sunrise views over the Atlantic
Davis Shores
Residential island neighborhood with marina access and a local feel
- ·Alligator Farm Zoological Park
- ·Salt Run waterway
- ·Local water sports and kayaking
A Brief History of St. Augustine
The story of St. Augustine begins on September 8, 1565, when Spanish admiral Pedro Menéndez de Avilés landed near the St. Johns River and established what would become the oldest continuously inhabited European city in the United States. The Spanish built forts and missions throughout northeast Florida, and the Castillo de San Marcos — construction begun in 1672 — still stands as the oldest masonry fort in the continental US, never captured in battle.
The city changed hands repeatedly: British (1763–1783), Spanish again (1783–1821), then American after the Adams-Onís Treaty. Florida statehood came in 1845. The Civil War saw the city relatively untouched physically, but Martin Luther King Jr. used St. Augustine in 1964 as a key battleground for civil rights demonstrations, including wade-ins at segregated beaches that helped accelerate passage of the Civil Rights Act.
Henry Flagler transformed St. Augustine in the 1880s, building the extraordinary Ponce de León Hotel (now Flagler College) and the Alcazar Hotel (now the Lightner Museum) to attract wealthy northern tourists — establishing Florida's tourism industry in the process. Today St. Augustine's economy remains built on its history and the 3+ million visitors who come annually to experience what no other American city can offer: six continuous centuries of habitation.
Top Attractions in St. Augustine
Castillo de San Marcos National Monument
The oldest masonry fort in the continental US (construction begun 1672). National Park Service site with ranger tours. Admission ~$15 adults.
St. George Street
Pedestrian shopping street through the heart of the Historic District — colonial-era buildings, museums, restaurants, and shops.
Flagler College (Former Ponce de León Hotel)
Henry Flagler's 1888 masterpiece — Gilded Age architecture in active use as a college. Guided tours available for a nominal fee.
Lightner Museum (Former Alcazar Hotel)
Flagler's second hotel is now a museum of Victorian-era art, cut glass, and curiosities. One of Florida's most interesting museums.
Colonial Quarter
Living history museum recreating 16th–18th century St. Augustine with costumed interpreters, blacksmithing, and musket demonstrations.
St. Augustine Lighthouse & Maritime Museum
165-step lighthouse with panoramic views of Anastasia Island and Matanzas Bay. One of America's most photographed lighthouses.
St. Augustine Beach
Atlantic Ocean beach on Anastasia Island, 10 minutes from the Historic District. Wide, clean beach with lifeguards seasonally.
St. Augustine Alligator Farm Zoological Park
One of Florida's oldest attractions (1893) — every known species of crocodilian plus native Florida wildlife. Excellent zipline over gators.
Anastasia State Park
Stunning 1,600-acre barrier island park with Atlantic beach, hiking, camping, and kayaking through salt marshes.
Fountain of Youth Archaeological Park
The supposed site of Ponce de León's legendary spring — archaeological exhibits, peacocks, and the famous sulfur spring.
Old Jail Museum
Restored 1891 county jail with guided ghost tours and history of law enforcement in Spanish and American Florida.
Government House Museum
Free museum in the city's historic government building covering 450+ years of St. Augustine history with rotating exhibitions.
Where to Eat in St. Augustine
Local recommendations for day-trippers from Ocala
The Floridian Restaurant
$$The most celebrated local restaurant in St. Augustine. Farm-to-table Florida ingredients, excellent brunch, and creative Southern cooking.
O.C. White's Seafood & Spirits
$$Waterfront seafood in a restored 1790s building on Matanzas Bay. Excellent grouper and shrimp; outdoor deck is outstanding.
Catch 27
$$$Creative modern seafood with a focus on local Gulf and Atlantic catch. One of the city's most sophisticated dining rooms.
The Raintree Restaurant
$$$St. Augustine fine dining institution in a restored 1879 building with Victorian elegance.
Casa Monica's Cobalt Lounge
$$$Rooftop bar at the historic Casa Monica hotel with excellent sunset views over the city.
Preserved Restaurant
$$$Farm-to-table dining in one of the Historic District's most atmospheric spaces — wood beams, brick walls, excellent cocktails.
Meehan's Irish Pub
$$Lively St. George Street pub with live music most nights. Not for fine dining — for a pint and authentic pub atmosphere.
The Ice Plant Bar
$$Craft cocktail bar in a restored 1927 ice plant. One of Florida's best cocktail programs; excellent charcuterie.
Price guide: $ = under $15 · $$ = $15–30 · $$$ = $30–60 · $$$$ = $60+
Where to Stay in St. Augustine
Budget
Comfort Suites St. Augustine North
Clean budget option with free breakfast north of the historic core ($80–130/night); drive or trolley into downtown.
Holiday Inn Express St. Augustine
Standard chain option with good value ($70–120/night) along US-1 corridor.
Mid-Range
Bayfront Marin House Historic B&B
Waterfront B&B on Matanzas Bay with historic rooms and excellent location ($160–260/night).
Saint Augustine Beach House
Boutique hotel steps from St. Augustine Beach ($130–220/night); excellent for beach-focused visits.
Luxury
Casa Monica Resort & Spa
The 1888 Flagler-era landmark hotel at the heart of the Historic District ($250–450/night). The quintessential St. Augustine stay.
Collector Luxury Inn & Gardens
Nine restored historic cottages surrounding a central garden and pool ($230–380/night). Unique, beautiful property.
Local Insider Tips for St. Augustine
Visit the Castillo de San Marcos early morning (open at 9 AM) to get the best photos and avoid the worst afternoon heat and crowds.
The Nights of Lights (November through January) transforms St. Augustine with millions of white lights — plan around it but expect crowds on weekends.
St. George Street is charming but heavily tourist-commercial; wander one block off it in either direction for quieter, more authentic streets.
The St. Augustine Lighthouse offers the best elevated view of the city and Matanzas Bay — the 165-step climb is worth it on a clear day.
Anastasia State Park (5 min from downtown) offers a far less crowded beach than St. Augustine Beach proper, with pristine Atlantic shore and excellent shelling.
Flagler College offers tours of the extraordinary Ponce de León Hotel interior, including the original Tiffany stained glass dining room — not to be missed at about $15 per person.
Annual Events in St. Augustine
Nights of Lights
St. Augustine's most famous event — millions of white lights transform the Historic District for two months. Nationally recognized as one of America's top holiday light displays.
St. Augustine Pirate Gathering
Weekend pirate festival with period-costumed participants, cannon demonstrations, and encampments throughout the Historic District.
Ancient City Road Race
Annual running event through the Historic District with 5K and 10K options along Matanzas Bay and historic streets.
Celtic Music & Heritage Festival
Three-day Celtic music festival in the Colonial Quarter and St. George Street venues celebrating St. Augustine's Irish and Scottish heritage.
Rhythm & Brews
Annual craft beer festival at the Historic District with local and regional breweries paired with live music.
Frequently Asked Questions: Ocala to St. Augustine
How far is Ocala from St. Augustine?
Ocala is approximately 100 miles from St. Augustine, about 1 hour and 40 minutes via SR-40 East to I-95 North.
Why is St. Augustine called America's Oldest City?
St. Augustine was founded in 1565 by Spanish explorer Pedro Menéndez de Avilés, making it the oldest continuously occupied European settlement in the United States — predating the 1607 Jamestown settlement by 42 years.
What is the Castillo de San Marcos?
The Castillo de San Marcos is the oldest masonry fort in the continental US, built by the Spanish beginning in 1672 from coquina stone. It's a National Monument operated by the National Park Service; admission is approximately $15 for adults.
What is the best time to visit St. Augustine from Ocala?
October through May offers the best weather. November through January features Nights of Lights, one of Florida's most spectacular seasonal events. Spring break (March) brings heavy crowds.
What are the Nights of Lights?
Nights of Lights is St. Augustine's annual holiday light event (November through January), where millions of white lights illuminate the Historic District. It's one of America's most celebrated holiday light displays and is listed as one of the "Top 10 Holiday Lights Displays" nationally.
Is St. Augustine walkable?
The Historic District is very walkable — St. George Street and the surrounding blocks are compact and pedestrian-friendly. The Old Town Trolley also provides hop-on/hop-off service throughout the district.
How much does it cost to visit St. Augustine?
Much of the Historic District is free to walk. The Castillo (~$15), Flagler College tour (~$15), and individual museums ($10–15) are the main paid admissions. Total can range from free to $50+ depending on attractions.
What is Flagler College?
Flagler College is a liberal arts college occupying Henry Flagler's 1888 Ponce de León Hotel — one of the most extraordinary Gilded Age buildings in the US. Tours are available to the public for a nominal fee.
Is St. Augustine good for families?
Very much so. The Alligator Farm, St. Augustine Beach, Colonial Quarter living history, and the Lighthouse climb are all excellent family activities.
What is the difference between St. Augustine and St. Augustine Beach?
St. Augustine (Historic District) is the inland colonial city; St. Augustine Beach is the Atlantic oceanfront community on Anastasia Island, about 10 minutes away by car.
Can I park for free in St. Augustine?
Some free parking exists in Lincolnville and on side streets, but the Historic District core requires paid parking. The Visitor Information Center garage offers the best central option, with the first hour often free.
What is the Lightner Museum?
The Lightner Museum occupies Henry Flagler's former Alcazar Hotel (1888) and houses a remarkable collection of Gilded Age art, cut glass, and Victorian-era curiosities. One of Florida's most interesting and undervisited museums.
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