This year marks the bicentennial of the official transfer of Florida, once a Spanish territory, to the United States in 1821. The Spanish ruled these shores off and on since Juan Ponce de León’s 1513 landing, but there are few signs of this legacy, save for the occasional historic site and place names like Boca Raton and Islamorada. This three-day Northern Florida road trip strings together landmarks with natural areas, all with unexpected connections to the state’s Spanish heritage.
What to drive
To truly get in the spirit as you drive along the Gulf of Mexico or under Spanish moss–draped canopy roads, you’ll need a convertible.
When to go
Northern Florida can get chilly, so plan your drive for late spring, before the start of hurricane season in June.
Day 1
Start in Pensacola, a naval town that hosted America’s first European settlement back in 1559—48 years before the British reached Jamestown. Grab a breakfast of patatas bravas and Gibraltar coffee at Polonza Bistro, named after the earliest Spanish name for Pensacola Bay. Walk six blocks to Plaza Ferdinand VII, the precise location of the 1821 territorial handover, and then stroll the historic district, past the 1805 Lavalle House and into the 1907 Mediterranean Revival T.T. Wentworth, Jr. Florida State Museum to see its City of Five Flags exhibit.
Take your time crossing the Panhandle by tracing the coastline on U.S. 98. In Fort Walton Beach, stop into the Indian Temple Mound Museum, which sits near an Indigenous-built earthen mound dating to about the year 850. Inside, the collection houses ancient ceramics and exhibits on the early Spanish explorers and pirates. An hour down the road, hit Rosemary Beach’s La Crema Tapas & Chocolate for garlicky Gulf prawns, tuna ceviche, and sipping chocolate like you’d find in Madrid.
As you approach Panama City, brake for beach time at St. Andrews State Park. Rent snorkels from the concession stand to hang with tropical fish and rays. Look out across the channel toward Shell Island, which was reportedly a treasure-burying spot for pirates.
After 90 minutes along the coastline, you’ll reach the oyster hub of Apalachicola. Centuries ago, the Spanish burned these bivalves’ shells to create the “tabby” concrete they used to construct their buildings. Toast the end of your day at Oyster City Brewing Company before heading two blocks away to the 1907 Gibson Inn, which just underwent a major overhaul. At the hotel restaurant, The Franklin, order a dozen oysters, topped with Jack Daniels brown butter and hot sausage, before bedding down for the night.
Day 2
Fuel up on locally roasted coffee at Bayside Coffee Co., just across Apalachicola Bay in Eastpoint, before heading onto the road. In an hour, you’ll reach San Marcos de Apalache Historic State Park, where the Spanish first built a wooden fort in 1679. A trail connects the fort's remnants and a Confederate-era magazine.
Cut north toward Tallahassee and the Mission San Luis, where both the Spanish and Apalachee lived in the 17th century. Today, it’s a living history museum centered around the state’s only reconstructed Spanish mission, featuring blacksmith and barbacoa demonstrations. (The complex is temporarily closed during the pandemic.)
For lunch, ask for a patio table at The Edison Restaurant, which overlooks the namesake waterfall in Tallahassee’s Cascades Park. When the U.S. took control of Florida in 1821, the governor sent envoys from Pensacola and St. Augustine to find a spot for a new, more centralized state capital, and they fell for this location’s natural splendor.
Take the long way out of town, heading east on Old Saint Augustine Road, a designated “canopy road” draped with Spanish moss. It’s one of the last remaining pieces of El Camino Real, which connected St. Augustine with missions and settlements out west.
You have some distance to cover this afternoon, so hop on I-10 before cutting south on I-75. Two hours later, just south of Gainesville, you’ll reach the impressive Paynes Prairie Preserve State Park. In the early 17th century, this land was home to the territory’s largest cattle ranch, owned by the Spanish royal treasurer. The park is now home to some 300 bird species (best seen on the La Chua Trail), in addition to some unexpected residents: a herd of reintroduced bison and Florida Cracker horses, which trace their ancestry to the equine companions of the conquistadors.
Continue to the town of Hawthorne for a dinner of frog legs and alligator at The Yearling Restaurant & Cocktail Lounge, named for the 1939 Pulitzer-winning novel by Marjorie Kinnan Rawlings, who lived a half-mile away. Check in to Micanopy’s Herlong Mansion Bed & Breakfast, which originated in the 1840s as a pinewood farmhouse before being transformed into the Corinthian-column-fronted mansion it is today.
Day 3
Your final destination is St. Augustine, which was founded in 1565, making it America’s oldest permanent European city. Zip through the backwoods of Central Florida on S.R. 20, then cross over the St. Johns River, which the Spanish called Rio de Corientes, or River of Currents.
Drive northeast on S.R. 207 until you reach Fort Mose Historic State Park, the site of the continent’s first free Black community, founded in 1738. More than a century before emancipation, this spot was the terminus of a southbound Underground Railroad: Enslaved people who crossed the border into the territory were freed if they pledged allegiance to the king of Spain and converted to Catholicism.
Head south on U.S. 1, past the kitschy Ponce de Leon’s Fountain of Youth Archaeological Park, and stop by the impressive Castillo de San Marcos National Monument, America’s oldest masonry fort. The Spanish began construction in 1672, using coquina, a type of limestone composed of fossilized shell fragments.
For lunch, make a reservation at the St. Augustine outpost of Tampa’s iconic Columbia Restaurant (the original is Florida’s oldest continuously operating restaurant), which is decorated with hand-painted Spanish tiles and a lion-studded courtyard fountain. You can’t go wrong with sangria and seafood-filled paella a la valenciana.
Choose your own historical adventure this afternoon. Love religion? Make a pilgrimage to the Cathedral Basilica of St. Augustine, a Mission-style church built in the 1790s. Want to learn how the colonists healed their sick? The Spanish Military Hospital Museum has tours about herbal remedies and surgeries. Interested in a historic home? Choose between the 1723 González-Alvarez House (a.k.a The Oldest House Museum Complex), the circa 1750 Peña-Peck House, or the 1798 Ximenez-Fatio House, which later became a woman-owned boardinghouse.
For dinner, indulge in a five-course coastal Spanish tasting menu (with wine pairings) at Michael’s, a transporting steakhouse set in the 1764 Buchanti House. Check in for the evening at the railroad tycoon Henry Flagler’s 1888 Casa Monica Resort & Spa, which features a Moorish Revival façade that might have looked remarkably like home to the conquistadors who walked these very streets centuries before.
