While Orlando and South Florida grab the attention and tourists, North Florida still manages to fly largely under the radar despite being home to America’s oldest (and arguably most beautiful) city and wide-open, pristine beaches.
The Sunshine State’s north has some of its most charming small towns, and on this 7-day road trip itinerary, we crisscross northern Florida from west to east to pass through some of them. We travel from Pensacola, kicking up our sandy toes and watching sunsets over the Gulf of Mexico before capping off our trip watching the sun rise over the Atlantic Ocean in the drop-dead gorgeous historic port city of St. Augustine, founded in 1565 as America’s oldest continuously habituated city. Along the way, we’ll learn more about the unique creatures who inhabit this area, from sea turtles to the colorful cast of local humans.
This isn’t your same old trip to Disney World. This is real Florida—old Florida—at its finest.
Days 1–2: “Florida’s Most Relaxing Place”
Head east on US-98 and FL-399 from Pensacola
Located about 25 miles east of Pensacola on the Gulf of Mexico’s barrier Santa Rosa Island, Navarre is a classic Florida beach town well off most Florida travel itineraries. In Navarre Beach, golf carts are perfectly acceptable modes of transportation on most streets. And why shouldn’t they be? After all, the town calls itself “Florida’s Most Relaxing Place.”
Tourism slogans aside, the laid-back stretch of white sand beach in the Florida Panhandle remains largely ignored by most of the visiting herds making their way towards the more heavily trafficked nearby spring break hubs of Destin and Panama City Beach.
Which is kind of the point. Uncrowded and unspoiled, this family-friendly community is known for seafood, sea turtles, and sand dunes, the latter of which can be most majestically viewed by driving through the beautifully windswept and largely human-free Gulf Islands National Seashore, just outside of town.
Back on Navarre Beach, Springhill Suites offers bang-for-your-buck beachfront quarters from which to sip frozen cocktails besides the lazy river pool overlooking the Gulf. Friendly locals will teach you how to say the town’s name (it’s pronounced “Nav-ARR”) while providing valuable intel on where to eat, including Beach House Social for upscale dinner or Juana’s Pagodas for casual lunch on the water.
You could do worse than renting wheels from Sage Golf Carts and puttering around town aimlessly, stopping at interesting points along the way like the cute Navarre Sea Turtle Conservation Center.
Days 3-4: “Florida’s Forgotten Coast”
Continue east on FL-399 and US-98
The roads become more remote along the 3-hour trek east as you cross into Franklin County en route to the charming historic fishing community of Apalachicola. This is the beating heart of this rural section of beachfront Florida known as “The Forgotten Coast.” With a vibe more reminiscent of the Old South than South Beach, this quintessential “Old Florida” town is a stunner that sneaks up on you in the most unexpected of places.
With quaint Victorian-era homes and more than 90 historic structures packed into a tight and highly strollable downtown district, “Apalach” (as locals call it) is known for oysters and still operates as one of Florida’s last functioning seaports. Yet modern touches like local breweries in warehouses and food trucks dotted throughout green spaces give the community a younger energy.
Apalachicola is best experienced by seeking out live music in one of its many good-time bars and restaurants such as High Five Dive Bar and Apalachicola Yacht Club. (If you’re there in the autumn, be sure to stop by Porch Fest Apalach, when residential front porches are transformed into live music stages.)
It is said that you are no more than 5 minutes from a fishing hole in this angling-obsessed community, where a diverse array of wetland environments,—bays and craggy marshes and rivers and wide-open Gulf waters—provide ample opportunities to reel in everything from redfish to marlin. For the best experience, wade out in the water and cast out a line on a stand-up paddleboard or hire a fun, knowledgeable local like Captain Danielle of Lady Guide Fly Fishing to show you the way before relaxing for the evening over tall tales from the sea and a plate of oysters at The Station Raw Bar, an appealing hangout in a remodeled gas station.
Built in 1907 with a wraparound wooden porch and beckoning rocking chairs, the newly renovated Gibson Inn is a local landmark and easily the best place to stay in town. Historically quaint yet cool like the town itself, the hotel’s Parlor Bar is a central gathering place from which to plan your next adventure which—by all means—should most definitely include the beaches of nearby St. George Island, a 22-mile barrier island that trades high-rise development (of which there is none) for crabmeat-stuffed grouper and sunsets over the water at casual local eateries like Blue Parrot.
Days 4-7: America’s Oldest City
Take I-10 east to Jacksonville, then I-95 south to St. Augustine
The next day, your long 4.5-hour drive will be worth it as soon you pull into the one and only Atlantic Ocean port city of St. Augustine, also spelled as Saint Augustine. Founded in 1565 as America’s oldest city, this breathtakingly scenic former Spanish settlement oozes colonial heritage at nearly every turn.
St. Augustine’s pedestrian-only main thoroughfare of St. George Street may be touristy, but that doesn’t make it any less mesmerizing. Wander the city beneath towering live oak and magnolia trees and don’t be afraid to travel off the beaten path, where fine dining at culinary hotspots like the French-inspired La Nouvelle integrate seamlessly with smoke-filled local dives such as Stogie’s Cigar Bar.
Leading tourist sights including the historic Lightner Museum and the Castillo de San Marcos (a 1670s-era Spanish castle and the continental United States’ oldest fort) are well worth the price of admission, with a tram tour from a local operator like Old Town Trolley Tours providing a fun way to check off a number of sights at once. Ghost bar tours such as the Original Haunted Pub Tour from Ghost Augustine are also a fun thing here, which hardly comes as a surprise in a town so full of eccentric characters like wild-eyed revelers dressed in pirate costumes and old hippies waving from bicycles covered in flowers.
This being Florida, let’s not forget that St. Augustine is also home to jaw-dropping white sand beaches like St. Augustine Beach, where the oceanfront expanse of nature comes as a welcome respite for those looking to relax in the sun after a long day of sightseeing. Following sunset on the beach, grab dinner nearby at the chic yet approachable Salt Life Food Shack before catching some seriously legit live blues at Café Eleven located down the street.
A variety of upscale historic homes unified by lush gardens has been painstakingly reassembled at The Collector Inn, offering one-of-a-kind accommodations within easy walking distance to most St. Augustine sights. The 30-room, adults-only luxury inn offers endlessly romantic vibes and a quiet seclusion reflective of the eclectic character of St. Augustine itself—a town whose whimsical, improvisational nature begs to be explored without agenda or itinerary.
