How to Build the Perfect Itinerary for a Winter Florida Road Trip

From Appalachia to the California coast, road trips are an Americana pastime that provide a more intimate, wanderlust-ful approach to travel. But while road trips are typically summer affairs in, like, 90% of the country, one state that shines brightest in the winter is Florida.

The Sunshine State ticks all the boxes for a requisite road trip too: it’s got shockingly varied landscapes and terrain, regional food galore, warm and sunny weather, national parks and theme parks, as well as the perfect combination of big cities, small towns, and everything in between. It’s also quite the hefty excursion — driving from one end of the state to the other, from Pensacola to Key West, takes about 13 hours. For context, that’s about the same length of time it would take to traverse all of California.

So if you’re looking to break from the mold and try a new kind of seasonal road trip this winter, one that includes everything from beachside tasting menus and palatial pink hotels to Mickey Mouse-shaped beignets and conch fritters, here’s the ideal itinerary for squeezing every last drop of orange juice out of one big Floridian adventure.

Pensacola

Start your road trip in the furthest edge of Florida, at a portion of the lanky panhandle so far-flung that it’s in the Central Time Zone. Pensacola is a sleeper hit of a city that deserves higher billing on the roster of Florida cities, what with its idyllic beachfront, its Blue Angels, its French Quarter-esque downtown architecture and its diverse array of high-caliber restaurants, bars, breweries and cafes.

On one side, you have Pensacola Beach, famed for its sugary white sand and nautical activities, like swimming, nighttime glow paddle boarding and the scarfing of seafood-stuffed omelets at Native Cafe. On the inland side of town, downtown Pensacola feels worlds apart from its beachy brethren with its historic architecture, museums, art and restaurants.

Enjoy a seasonal pasta tasting menu at Angelena’s, and explore the latest and greatest at the Pensacola Museum of Art, a former jail-turned-gallery that features rotating exhibitions like the Warhol-filled Vandals to Vanguards. Grab a beer at Perfect Plain Brewing Co. and take in a show at Pensacola Little Theatre, a haven of inclusivity and the arts, where recent productions included an immersive, interactive take on Romeo and Juliet.

And be sure to keep your eyes peeled for the imminent reopening of the National Naval Aviation Museum, the home base for the famed Blue Angels, and a mammoth museum that’s been inching toward a grand public reopening for the first time since 2019.

In terms of where to stay, there’s an easy-breezy place on the beach that goes by the name Margaritaville. Need we say more?

The Panhandle

Venturing eastward into the pith of Florida, you’ll drive along the Gulf Coast panhandle through some towns so pastoral and twee they seem almost farcical. That’s because towns along State Road 30A, like Seaside, are so cartoonishly perfect that The Truman Show was filmed there. Today, rather than being entwined in an elaborate collaborative hoax by its residents, you can frolic on the beach, hike the trails at Grayton Beach State Park, dine at food trucks along Airstream Row or simply stroll through town, marveling at the pastel cottages and Stepford vibes.

Other nearby towns are just as chillingly perfect, like Rosemary Beach and Watercolor, while Miramar Beach is home to all manner of shopping, dining and entertainment, including a farmers’ market, palatial movie theater and restaurants like The Craft Bar and a seafood joint from Emeril Lagasse.

From here, drive inland and head further east for a stop in the state capitol, Tallahassee. Here, you’ll find one of Florida’s best bakeries, the doughnut-famed SoDOUGH Baking Co., and tour the free-to-visit capitol building. Other Tallahassee treats include the hallowed Bradfordville Blues Club, the gallery-filled Railroad Square district and paddling aplenty. And if inevitable alligator sightings weren’t enough, there’s also an 1,800-foot rattlesnake statue that feels like a can’t-miss.

Amelia Island

Next up, trek another three hours east to drop anchor on Amelia Island, Florida’s northernmost barrier island located just over the river from Georgia — with plenty of Savannah-esque Spanish moss to prove it. Much quieter and more serene than most of Florida’s typically well-trod beachfront, the 13-mile island is teeming with activities, attractions and lore, from swashbuckling pirate pastimes and Civil War-era garrisons to bucolic fudge shops and olden saloons along Fernandina Beach and an annual shrimp festival that looks like the Mardi Gras of crustaceans.

Rest your head in style at The Ritz-Carlton, Amelia Island, a recently renovated stunner of a property, located right on the beach and boasting an array of splurge-worthy amenities like zero-gravity hammock spa treatments, ornate tasting menus at Salt, an 18-hole golf course and both indoor and outdoor pools. For outdoor recreation, the hotel employs a resident naturalist who leads guests on nature walks, or you’re free to explore any of the island’s beaches, with 40 public access points spanning the shore.

At Amelia’s northernmost nexus, Fort Clinch State Park is a fascinating place to explore Civil War history, forested trails and the St. Mary’s River that serves as the Florida-Georgia line, if you will. In terms of dining, you’ll find seafood galore at spots like Timoti’s Seafood Shak, Cedar River Seafood and Coast back at The Ritz, while the timeworn Palace Saloon is a mandatory stopover for Pirate’s Punch in an allegedly haunted bar that’s been around since 1903.

Orlando

At this point, you’ve had enough panhandle fun for one trip, so it’s time to head south to another underrated city that doesn’t get the cred it deserves. Too often, Orlando gets lumped in with its nearby theme parks, when it actuality the city is a metropolitan mecca all its own. It’s actually about 30 minutes away from Disney World, and the vibes could not be more different.

Sure, you can — and honestly should — clock some time in the Most Magical Place on Earth. The new Guardians of the Galaxy: Cosmic Rewind ride at EPCOT is mind-blowing, the Mickey-shaped beignets at Disney’s Port Orleans Resort are a revelation and Disney Springs is a full-blown spectacle of entertainment, top-quality eats and endless shopping. But don’t conflate Disney World with Orlando, a vibrant city with distinct neighborhoods, Michelin-caliber restaurants and staggering festivals that look like Burning Man-meets-Coachella.

Start with a traipse around Lake Eola in downtown Orlando, a swan-filled alcove with close proximity to chic spots like Deeply Coffee, The Robinson Cocktail Room and The Wellborn — a boutique inn and restaurant with exciting drinks and snacks like Brie grilled cheese, guava-slathered pork ribs and corn beignets. (They may not be Mickey-shaped, but they’re superb.) Then branch out and hit some neighborhoods, venturing into Ivanhoe Village to shop for one-of-a-kind furniture and furnishings at Washburn Imports (psst there’s a wine bar inside), or the Milk District for beer at Sideward Brewing Co., or Audubon Park for omakases at Kadence and the most coveted cookies in town.

St. Petersburg

Criss-crossing the state, it’s time to pop back over to the Gulf Coast for a stint in St. Petersburg. Only about two hours from Orlando, the endearingly nicknamed “Sunshine City” is full of surprises all its own. Like the waterfront Salvador Dalí Museum, the tiki bar perched at the very end of the colossal St. Petersburg Pier and stunning Mediterranean food at Allelo. Also, you probably weren’t expecting to find a hub of western art in Florida, but here we are.

Then there’s The Don CeSar hotel on St. Pete Beach, a “Pink Palace” so storied and iconic that it’s allegedly the sight of lovelorn ghosts. Managed by Davidson Resorts and complete with two outdoor pools and a private beach equipped with cabanas, the hotel has hosted many a celebrity and dignitary since its inception in 1928, from Elton John to F. Scott Fitzgerald, and it remains a bastion of pomp, circumstance and seaside luxury. It’s also a hub for foodies, with its recently renovated Maritana serving up roasted bone marrow and lobster gnudi with a side of swagger. For something a smidge more casual, cozy up by an outdoor fire pit at The Rowe Bar, with prohibition-era cocktails and the prettiest key lime pie you’ll ever eat.

Miami

For some quintessential fun in the Florida sun, set your GPS to South Florida and venture to the holy grail of beachside debauchery: Miami. About four hours from St. Pete, including a drive across Alligator Alley along I-75, Miami truly feels like the city that never sleeps — and that’s only partly because the traffic never seems to subsist.

All over town, from neighborhoods like Coconut Grove and Little Havana to Brickell, artsy Wynwood and Miami Beach, there are seemingly endless things to do and devour. In addition to a requisite stint on South Beach for some see-and-be-seen sun-bathing, newer additions to the city are elevating Miami to a whole new stratosphere of culinary and cultural prowess. Chief among these new entries is The Tambourine Room by Tristan Brandt, a clandestine 18-seat tasting menu restaurant nestled inside The Carrillon Miami Wellness Resort. With its show-stopping spree of intricate, ornate dishes and esoteric wine pairings, it’s the type of buzzy newcomer that seems destined for Michelin-starred glory.

Over in Wynwood, when you’re done selfie-ing at the Wynwood Walls, the new Arlo hotel is home to MaryGold’s, a “Florida brasserie” from local celebrity chef Brad Kilgore and Bar Lab. For calamari with killer views, settle in on the beachside patio at Ocean Social, a renovated entry at Eden Roc Miami Beach, with sensational seafood, avocado-strewn pizzas and some of the best frosé in the state.

While in town, also snag tickets to Superblue, a stunningly immersive art experience overflowing with flowers and soapy “clouds,” and savor some culture at Cafe La Trova, a Little Havana hot spot known for its Cuban jazz bands, exquisite cocktails and shareable dishes from lauded chef Michelle Bernstein.

Everglades National Park

It’s hard to believe, but barely an hour from the calamity of Miami Beach is one of the largest nature preserves in the contiguous U.S. Clocking in at roughly 1 million acres, Everglades National Park is the third largest national park in the lower 48 states (trailing just Yellowstone and Death Valley), and by far the largest east of the Mississippi.

Driving into this vast wilderness feels like driving into real-life Jurassic Park, but instead of dinosaurs, it’s dinosaur-looking alligators and crocodiles — Everglades is, after all, the only place on Earth where the two species co-exist, along with manatees, dolphins, sharks, the rare Florida panther and invasive Burmese pythons. Between the wildlife, the magnitude of the wilderness, and the utter lack of WiFi, this place isn’t for the faint of heart. But it’s a road trip requisite for leisurely hiking trails (they’re all flat and relatively short, just don’t you dare forget the bug spray) and paddling.

The Flamingo Marina, located on the coastal southern tip of the park, is a great place to rent kayaks or canoes and paddle up the creek to Coot Bay, or into the oceanic Florida Bay. If you’re the camping type, there’s a large campground for tent and RV camping at Flamingo, or you can splurge on a houseboat. Be sure to stop at the Anhinga Trail near the park entrance, a short boardwalk-style loop trail where you’re all but guaranteed to see multiple gators.

Florida Keys

Entering the final phase of the Florida road trip, the Keys are so distinct and unique compared to the rest of the state that it feels like you’re in a different country — a country populated by feral roosters, conch fritters and hardwood hammock.

Your first stop should be Baker’s Cay Resort, a tranquil Davidson Resorts oasis on Key Largo. Home to one of the only sandy beaches on the Keys, the open-air resort feels more like Hawaii than Florida, with its lush mangrove forests and hardwood hammock habitat, its tiki bar and its waterfall-clad pools. Sustainability and conservation are a central tenet at the resort, where water filling stations are located all over the property, aluminum bottles sub in for plastic and the “Dock to Dish” dining program that links diners with small fishing communities to emphasize local, sustainable seafood. This philosophy is most apparent at seafood-centric Calusa, and at Dry Rocks, a tequila-focused bar that pours its own proprietary Reposados and Añejos from Patron, a brand that puts concerted efforts into water recycling and composting with agave fertilizer.

Then, punctuate your Keys drive with a grand finale in Key West, a veritable wonderland of eccentricities and kitsch. Check out spots like Blue Heaven, a classic Key West haunt with a huge patio, a “rooster graveyard” and Floridian-Caribbean comfort food like BBQ shrimp, jerk chicken and of course, key lime pie. For something a little less beach bummy, enjoy a tasting menu at Little Pearl, where seasonal dishes run the gamut from curried shrimp bisque and barbecued eel yakitori to flame-seared hamachi and veal osso buco. Clock some time on Duval Street, the main drag in town lined with saloons, cheeky gift shops, inns and mermaid crossing signs, then explore The Ernest Hemingway Home & Museum, a French Colonial-style estate that’s open for tours — and filled with cats.

Dry Tortugas National Park

For the final leg of your Florida road trip, you’re gonna need to park the car and board a ferry, because the westernmost part of the state is a smattering of small keys some 70 miles past Key West. Dry Tortugas National Park, for its utter remoteness in the middle of the Gulf of Mexico, only accessible by a 2.5-hour boat ride, is easily one of the most underrated national parks in the country. The park is 99% water, which basically necessitates a bit of swimming or snorkeling to fully experience it, both of which can be done off Garden Key, the main island where the ferry docks.

Anchored by the colossal brick-built Fort Jefferson, the key is surrounded by an underwater snorkel trail through the third largest coral reef on the planet, and beaches on the north, east and south sides of the island. The fort itself is a marvel of Civil War-era lore and structural ingenuity, once used to protect U.S. harbors from enemy ships and subsequently serve as a faraway prison for war criminals.