Flo-ridin’: The Best Florida Road Trips

Florida—that great geographical phallus so symbolic of America’s Freudian id—is a land of glorious paradoxes. Do we call it the South? An extension of the Caribbean? The Sixth Borough of New York City?

The farther north you wander up the sun-soaked peninsula, the more you find yourself in the Deep South, where drawls, NASCAR fandom, and sweet tea seep in from Georgia and Alabama. Venture into South Florida, from roughly Ft. Lauderdale down, and enter an exclave of Latin America—a colorful melting pot of Cuba, Brazil, Venezuela, Haiti, and Puerto Rico. Behold the state that reared Pitbull, Gloria Estefan, and Enrique Iglesias on one end and Lynyrd Skynyrd, Tom Petty, and the Allman Brothers on the other. Where lunch might be medianoches and cafe cubano and dinner fried chicken, collards, and sweet tea.

While the Sunshine State comprises a motley cultural quilt, common threads run throughout—heavenly weather, stunning beaches, and local spirit as warm and sultry as the climate. Ordered in consecutively increasing distances from Miami, the destinations below showcase Florida’s kaleidoscopic variety. So buckle up, throw on Damn the Torpedoes or the latest hits from Rick Ross, and let the ocean breeze set your soul at ease. Here are the best road trips in the great state of Florida.

Disclaimer: Check the news for updates on rogue gators, hurricanes, or the latest misadventures of Florida Man.

West Palm Beach

West Palm Beach, Florida

1 hour and 20 minutes from Miami

Boat shoes and Madras shorts. Martinis on the aft deck. Beach clubs more exclusive than Yale’s Skull and Bones Society. Welcome to West Palm Beach, the Nantucket of Florida.

West Palm Beach might be a blueblood bastion, but you don’t need to be a billionaire, or a cast member of Desperate Housewives, to appreciate the charms of this idyllic enclave. Sure, many come here to revel like robber barons—the restaurants and shopping are legendary—but the spectacular beaches and islands around West Palm Beach offer luxury that doesn’t cost a penny.

Laze the hours away beside swaying palm trees and crystalline waters at Peanut Island, a breezy islet only 15 minutes from downtown. Later, don your Persols and Vineyard Vines, and stroll Palm Beach’s handsome, palm-lined avenues. Clematis Street, a thoroughfare glittering with designer boutiques, Italian sports cars, and haute restaurants, could pass for an earthly replica of Anna Nicole Smith’s gilded description of heaven. Flagler Steakhouse, a mainstay for seafood towers, aged steaks, and rare wines, is glitzy enough to elicit approving smiles from even the most discerning of pearl- and Lily Pulitzer-clad mistresses. You can even eat well on the cheap in West Palm—just cruise over to Nick’s Diner, where the All-American breakfasts and Reuben sandwiches complement the vintage decor.

If you visit in the spring, snag a ticket to SunFest, a music festival as exuberant as Coachella or Bonaroo—but with the bonus of the beach.

Islamorada

1 hour and 45 minutes from Miami

Trace the route of Jake Gyllanhaal’s tough-guy hero in Roadhouse, and take the Old Seven Mile Bridge from Miami to Islamorada, an archipelago between Key Largo and Marathon. While much of the Florida Keys are overrun with resorts and kitschy shops, Islamorada has held on to the slow-motion, tropical languor that anchored poetic souls from Hemingway and Tennesee Williams to Jimmy Buffet to these Elysium Isles.

The shallow shoals around “The Sport Fishing Capital of the World” teem with aquatic fighters like tarpon, bonefish, and mahi mahi. While fishing’s status as a sport might be debatable, there is no doubting the elite athleticism of the kite-surfers and windsurfers who likewise flock to Islamorada. For those who favor Keith Richards’ famous fitness regime, lifting bottles to lips, post up at sunny Anne’s Beach to work on your six-pack—of Florida Keys Brewing Co Pilsner, that is.

Nature might be Islamorada’s chief draw, but the archipelago also boasts a handful of funky little manmade enclaves. Spend an afternoon wandering through the stalls of greengrocers, crafts-makers, and food trucks at Morada Way. After the market closes, walk to the beach to catch the sun setting upon waters the color of Blue Raspberry FourLoko. The affordable, no-frills bungalows at La Jolla Resort, right on the beach, are tailor-made for lovebirds or those seeking refuge from the crowds—the kind of hideaway Jimmy Buffet or Papa Hemingway would have loved.

Everglades City

1 hour and 45 minutes from Miami

The Everglades, home to scores of endemic birds, reptiles, and plants, are an ecological treasure trove. While much of the Everglades are protected by the National Park Service, the grand southern swamplands are home to a few fascinating human settlements.

Coat your epidermis with DEET and plunge headlong into the marsh at Everglades City, a lively port where the oceanic swamp unites with the Gulf of Mexico.

Joe’s Stone Crabs in Miami might be Florida’s most celebrated house of succulent crustacean flesh, but seafood shacks across Everglades City sell stone crabs at a fraction of the price. Feast on stone crabs, oysters, and fresh fish at Triad Seafood Market, a fishmonger and cafe right on the docks.

St. Petersburg

4 hours from Miami

Tampa Bay’s sister city, the groovy Gulf Coast town of St. Petersburg is renowned for golf, fishing, and nigh-perfect weather year-round. St. Pete has long attracted retirees, but a stroll along the boardwalk, a wooden avenue humming with watering holes, fit beach-goers, and seafood shacks, quickly dispels jokes about Heaven’s Waiting Room.

A rose-colored palace with sunny foyers and palm-lined courtyards, The Don CeSar is peak Florida. Book dinner reservations at Maritana, Don CeSar’s flagship restaurant, for plates of fresh seafood, wagyu steaks, and oysters pulled from the ocean the same day. Later in the evening, as the sinking sun drips molten gold into the Gulf, mosey over to The Bends, a tiki bar favored by fishermen, salt-brined ne’er-do-wells, and the occasional tourist.

St. Pete has burgeoned into Florida’s craft beer capital. The hot weather inspires lighter brews like Helles and Pilsners, but 3 Daughters Brewing churns out commendable IPAs, ciders, and stouts to boot. Follow The Gulp Coast Beer Trail to hit a medley of St. Pete’s hoppy havens. The Salvador Dalí Museum in St. Pete’s houses one of the world’s finest collections of artwork by the eccentric Catalunian master.

Jacksonville

5 hours from Miami

I know a Southern belle who lives by sea/she sings the blues and R&B. Jacksonville, the busy port city in North Florida, should be on every music lover’s bucket list. From Lynyrd Skynyrd and the Allman Brothers to Ray Charles and Shinedown (and the dubious honor of Limp Bizkit), Jacksonville is up there as one of America’s most fecund musical breeding grounds. Stop by the Florida Theatre to pay homage to the storied stage that has seen the likes of Elvis, Greg Allman, and Ronnie Van Zant. Or, for an intimate venue hosting rockin’ local outfits, check out 1904 Music Hall.

Fried fish and fried chicken. Hush puppies. Tea sweeter than Ray Charles crooning “I Can’t Stop Loving You.” Expect all the wonderful Southern fare your arteries can handle in Jax. Potter’s House Soul Food Bistro is a stalwart for superbly smoked BBQ, baked beans laden with ham hocks, and peach pies worthy of a Florida granny’s Thanksgiving dessert table. Congaree and Penn, a farm in the pine forests outside Jacksonville, treats guests to beers and ciders brewed on-site and a menu crafted with organic produce grown within eyeshot of your dinner table. The shrimp and grits, made from corn milled on the farm, are delicious enough to compel an old-school Charleston chef to hang his toque in defeat. Follow it with the refreshingly zippy mango mousse.

In the era before Hollywood, Jacksonville was America’s winter cinema capital, the premier filming location when cold weather compelled directors and actors to leave New York City. Spend an educational afternoon perusing Norman Studios to learn about the history of silent film and African-American cinema in the early 20th century. The MOCA, one of the oldest modern art museums in the nation, is another Jax cultural gem promising hours of edification and serenity.

Live Oak

6 hours from Miami

Welcome to Old Florida, old boy. On the banks of the Suwannee River, Live Oak seethes with lore, music, and romance—it’s a town reminiscent of a miniature Savannah or Charleston.

The Brown Lantern is a frozen-in-time local eatery, serving delicacies like fried cheese, chili dogs, and classic burgers. Prices likewise reflect a bygone era—almost everything on the menu is under $10. Rest your bones in the peaceful bucolic setting of Kokoma Farms. After the sun goes down, the gentle white noise of insects—the primordial sound of the Deep South—lulls weary heads to sleep better than a sound machine.

If you’re in Live Oak in June, catch the annual Live Oak Music Festival, an eclectic jamboree drawing musicians from across the South. Under the canopy of ancient, moss-cloaked live oaks, revelers bliss out to the dulcet melodies of folk, rock, blues, and country.

Pensacola

10 hours from Miami

Two hours from Tallahassee and one hour from Mobile, Pensacola is the grand finale of our Floridian highway odyssey. While Pensacola has all the charms of a large city—excellent restaurants, noteworthy breweries, and a panoply of cultural institutions—it still exudes the relaxed vibes of a beach town. After riding this strange torpedo called Florida out to the end, Pensacola beckons you, weary traveler, to take a load off and chill out.

Retirees and naval cadets compose a large percentage of Pensacola—with the former come excellent restaurants; with the latter, a slew of rip-roarin’ bars. Dine on screaming fresh oysters, scallops, and snapper paired with rocket-fuel martinis at Pearl and Horn. For a seafood bonanza worthy of King Neptune’s banquet hall, drive to Joe Patti’s, a market hall stocked with every edible treasure from the Gulf. Beat the heat with an icy-cold pilsner on the patio of Perfect Plain Brewing The Pensacola brewery crafts noteworthy IPAs, stouts, and light lagers as well as artisanal malt liquor packing a whopping 10% ABV.

Flora-Bama, a watering hole right on the Florida-Alabama line, is the best beach bar in these United States—just ask Kid Rock, Kenny Chesney, Hank Williams Jr., and countless other country legends and rock stars who have graced the stage of this national treasure. Raise a tequila shot to spring break, youthful indiscretions, and University of West Florida sororities and bask in the euphoria of the axis mundi of the Redneck Riviera. Here, gentle reader, is Florida’s spirit distilled as potently as the rum in a bushwhacker, Flora-Bama’s signature drink.

Johnny Motley has written for The Daily Beast, Matador Network, Cool Material, and more. He’s on Twitter @johnnymotley and Instagram @motjohnny.

West Palm Beach and Islamadora photos courtesy of Visit Florida

Pensacola photo courtesy of Perfect Plain Brewery

Live Oak photo by Michael Rivera, used under a CC BY-SA 4.0 license

Everglades City photo by Guillaume Capron, used under a CC BY-SA 2.0 license