I stressed in my last post that Florida is chock-full of unique adventures and awesome road trip opportunities. I highlighted the drive from Naples to Miami Beach—a smorgasbord of gator-infested jungle, island retreats and big-city exploits. It’s stereotypical Florida at its best, so tourists to the state wouldn’t be disappointed making that drive.
But this next drive is even better. Why? Because I’ll take authentic Florida over stereotype any day.
#2: Fernandina Beach to St. Augustine: Why is this authentic Florida? You’ll start to see in Fernandina—an island city with enough seafood, Southern charm and Victorian architecture to make Paula Deen squeal. Fernandina Beach, situated on Amelia Island in northeast Florida, is known as the ‘Isle of Eight Flags’ due to its long history of territorial claims and battles. You’d do well to spend an hour or so here, strolling through its historic downtown and enjoying its famed shrimp industry, its unique Revolutionary and Civil War heritage and its quirky shops.
When you finish exploring Fernandina, take State Road A1A south (SR A1A is Florida’s most celebrated and historic beachfront highway, and you’ll stay on this road almost the entire day). Continue through Amelia Island and cross Nassau Sound into Big Talbot Island State Park, a massive nature preserve about 20 miles east of downtown Jacksonville. The marshes, subtropical vegetation and Atlantic Ocean views make this a really scenic drive. You’ll continue south through Little Talbot Island State Park and Fort George Island before taking the St. Johns River Ferry across the river to Mayport (the ferry fee is $5 per vehicle). If you have time you should check out Kingsley Plantation on Fort George Island, the oldest remaining plantation house in Florida, as well as its old slave quarters. This is a rare opportunity to experience first-hand how slaves and plantation-owners lived and worked in the Antebellum South.
Cross the river and eat lunch at Singleton’s Seafood Shack in Mayport (located at 4728 Ocean Street). If you think you don’t like seafood, try it anyway. You’ll have a life-changing experience, trust me. Other than the scrumptious food, you’ll enjoy watching the old shrimp boats cruise up and down the river from your table. Very chill.
Continue on SR-A1A south through Atlantic Beach and into Neptune Beach. These are two bustling coastal communities, but I wouldn’t stop until you get to Jacksonville Beach. This is one of my favorite places to play. There’s plenty of white sand, warm water and, especially important for road trippers, beachfront parking! Spend an hour or two soaking up the sun—this is what Florida is all about. Then drive south through Ponte Vedra Beach (you should take Ponte Vedra Boulevard; it will connect back with A1A) and admire this ‘Beverly Hills’ of northern Florida. Gargantuan mansions, palm trees and immaculate golf courses stretch as far as far as the eye can see.
As you exit snobby Ponte Vedra, you’ll head south down one of my favorite stretches of highway in the country—your final leg of A1A until you reach St. Augustine. This, to me, is pure Florida. You’ll drive through the Guana River Wildlife Management Area, with its deserted beaches and undeveloped coast, teaming with sea turtles and shark teeth. This is how Florida looked to the first explorers hundreds of years ago—pristine and undisturbed. You’ll travel south and see old taverns, historic houses and quiet beach communities. No nightclubs or spotlights or celebrities on this stretch of coast. It’s a calm, relaxed part of Florida, made brilliant with the pervasive and spectacular blue sea, stretching to the east until forever. It’s wonderful here.
You’ll finally enter St. Augustine, and if you’ve never been here before, you’re in for a treat. This is the oldest city in America and you can tell the minute you drive into the ancient town. I could write an entire blog post about St. Augustine (which I will, in the future), so suffice it to say that there are a million things to do and see here. From Castillo de San Marcos fort to Flagler College to St. George Street—pirates, ghosts and tourists have raved about St. Augustine for 500 years. I would recommend eating dinner at one of the pizza places on St. George Street, but there are too many good restaurants here to recommend just one.
Follow this itinerary and you’ll have an awesome day. Granted, I’m biased since I grew up in this part of Florida. But as LeVar Burton says, you don’t have to take my word for it. See for yourself.
Total Miles Driven: 60
Check out Florida’s #1 drive next week.

St. Augustine skyline