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The best road trips from Miami

Charming beach towns, iconic architecture and so much more await at the best road trip destinations from Miami.

Falyn Wood
Written by
Shayne Benowitz
Contributor
Falyn Wood
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If you’re looking to experience all that Florida has to offer, Miami is the perfect starting point. Drive a few hours south and you’ll hit Key West, a boozy tropical paradise fit for pirates and poets alike. Trek west across I-75 to discover Naples, a land of laid-back beach resorts populated by friendly Midwestern snowbirds. To the north, Palm Beach oozes Old Florida (and old money) opulence, while Tampa and St. Pete serve up plenty of art, culture and locally brewed craft beer. Florida may be long, skinny and overwhelmingly flat, but this beautiful, strange peninsula is anything but one-note. When you’ve had your fill of tanning at the best Miami beaches, exploring Miami’s many parks or sipping fruity cocktails at the city's top waterfront bars, there’s really only one thing left to do: get out of town. So hop in, we’re going road-tripping!

Road trips from Miami

Distance and drive time: 70mi, 1hr

Travel north from Miami the same distance you would south to the Keys and you’ll arrive in the United States’ epicenter of privilege and luxury. Palm Beach’s riches are there for the taking—so long as your tolerance for lunching ladies, pastels and general clichés of wealth is strong.

Eat: The Breakers (1 S County Rd; 561-655-6611, thebreakers.com) is a Palm Beach institution, and so is Sunday brunch at its restaurant the Circle. If the dramatic dining room and its 30-foot vaulted fresco ceiling don’t convince you, perhaps the extravagant buffet—complete with a raw bar, carving stations and a lavish dessert spread—will. A strict resort-wear policy is enforced (no jeans, tees or hats, please). This is Palm Beach, after all.

Drink: The Leopard Classic Martini at the Leopard Lounge (363 Cocoanut Row; 561-659-5800; chesterfieldpb.com) is prepared exactly as we like it: vodka with dry vermouth, chilled and topped with three olives. Black lacquer walls, leather banquettes and leopard print carpet are a serious mood at this sultry spot inside the Chesterfield Hotel, striking just the right level of throwback decadence. Nightly live music and a vast selection of rum, whiskey and bourbon make the Leopard Lounge a popular destination for both locals and visitors.

Stay: A historic boutique hotel and longtime stalwart of Palm Beach society, the Colony (155 Hammon Ave; 561-655-5430, thecolonypalmbeach.com) is a riot in technicolor pastel, floral and palm-frond prints. Don’t skip the cabaret dinner show at the Royal Room; it’s followed by a rollicking after-party with sing-alongs and martinis around the piano.

Distance and drive time: 70mi, 1hr

Even the northernmost city of the Florida Keys subscribes to Jimmy Buffett’s “changes in latitude, changes in attitude” philosophy, which kicks in the moment you exit Florida City (about a 45-minute drive from the center of Miami) on your way to the Overseas Highway—the main artery uniting the string of islands. Life moves slower here (so do the cars) and things open and close early. Come sunrise, don’t be surprised if you’re the last snorkeler to reach the waters off John Pennekamp State Park (102601 Overseas Hwy; 305-451-6300, pennekamppark.com) or the last to sit down to breakfast at the local diner.

Eat: For a slice of Key Largo kitsch (and key lime pie, of course), Mrs. Mac’s Kitchen (99336 Overseas Hwy; 305-451-3722, mrsmacskitchen.com) is a tropically styled diner that’s been serving hard-to-resist dishes like lobster and grits, a relleno-style fish of the day and a grilled fish Reuben sandwich since 1976.

Drink: On your way to the Keys, opt for the road less traveled: Card Sound Road, an alternate route to Key Largo, boasts Alabama Jack’s (58000 Card Sound Rd; 305-248-8741), a ramshackle waterfront fish restaurant where the beer is ice-cold and the conch fritters and smoked-fish dip are always fresh and full of flavor.

Stay: Playa Largo Resort & Spa (97450 Overseas Hwy; 305-853-1001, playalargoresort.combrings an unprecedented touch of luxury to Key Largo and a welcome alternative to the usual boutique properties. Head straight to a hammock on the beach near the lagoon-style pool, order a margarita and don’t go back to your room until after sunset.

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Distance and drive time: 125mi, 2hrs

Nestled between the pristine Gulf of Mexico and the gritty Everglades, Naples is not your typical beach town. Stroll down the neatly landscaped Mediterranean Revival–style downtown district, where you’re most likely to spot snowbirds. Shed some layers for a walk down the rough-and-tumble Fifth Avenue South, and join locals hoisting longboards en route to the beach. Whatever your seaside style, you’ll find it in Naples.

Eat: On the off chance you’re carbo-loading at the beach (this is vacation), Osteria Tulia’s regional Italian menu is full of reasons to indulge (466 Fifth Ave South; 239-213-2073, osteriatulia.com). Work your way through the list of artfully prepared small plates, like the caramelized sprouts and crispy fried pig ears, and pared mains of which the classic cacio e pepe bucatini with sheep’s-milk cheese is simply phenomenal.

Drink: Head straight from the beach to the Turtle Club (9225 Gulfshore Dr; 239-592-6557, turtleclubnaples.com), and watch the sunset from one of the outdoor tables. Feel the sand between your toes while you look out onto the Gulf and sip a Paddle Boarder, a mango piña colada made with coconut rum.

Stay: Looming above a mangrove estuary that leads to a sublime secret beach, Naples Grande (475 Seagate Dr; 239-227-2182, naplesgrande.com) boasts chic rooms with oversize balconies, as well as three pools surrounded by beautiful landscaping. Zoom down one of the waterslides or hide in your gulf-view suite; the accommodations offer equal parts revelry and relaxation—just like Naples itself.

Distance and drive time: 160mi, 3hrs 30mins

A sunset sail aboard Schooner America 2.0 (Key West Bight Marina, Margaret St; 305-293-7245, sail-keywest.com) combines many of Key West’s greatest pleasures: boating, those famous pink skies and outdoor drinking. Before your night spirals into a blurry good time on Duval Street, take in the island’s offshore beauty aboard a majestic restored wooden sailboat. You’ll want to ease into the hard-hitting fun this slow-moving town is known for.

Eat: By husband-wife duo Tommy Quartararo and Kristen Onderdonk, Little Pearl (632 Olivia St; 305-204-4762, littlepearlkeywest.com) is a hit with critics and people in the neighborhood. Stick out the wait for a chance to taste one of the city’s most creative seafood menus, featuring comfort food classics like the lobster and crab pot pie.

Drink: Just one block south of Duval Street is the Green Parrot Bar (601 Whitehead St; 305-294-6133, greenparrot.com), a local watering hole with live music, a great jukebox, trippy decor, pool tables and a crowd that spills onto the sidewalks as the night goes on. Around these parts, the drink of choice is a round of Boot Beer Barrels—a shot of root beer schnapps plunged into a rocks glass of Miller Light. Now, chug!

Stay: To experience the hipster side of the island (yes, that’s a thing), check into Oceans Edge (5950 Peninsular Ave; 305-809-8204, oceansedgekeywest.com), a luxurious resort on Stock Island, which is considered the “old” part of Key West. The shipyards, shrimp boats and artist studios in the area are cool once again.

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Distance and drive time: 260mi, 4hrs 30mins

Though known for its chill beaches, St. Petersburg also offers a surprisingly cosmopolitan escape thanks to the culture-obsessed downtown district along Central Avenue. Case in point: the world-class Dalí Museum (1 Dali Blvd; 727-823-3767, thedali.org) housed inside a building designed by Yann Weymouth that’s worthy of the Surrealist master. And just as picturesque as the architecture and the view of Tampa Bay is the seaside that brought you to St. Pete in the first place.

Eat: Red Mesa Cantina (128 3rd St South; 727-896-8226, redmesacantina.com) in the heart of downtown is standard for a weekend outing. Prepare to spend hours lingering over southwestern dishes and cocktails, as Cantina houses one of the area’s largest selections of tequila and mezcal.

Drink: For serious speakeasy vibes and a craft-cocktail program to match (the spot takes its hand-carved ice portfolio seriously), slip into the Mandarin Hide (231 Central Ave North; 727-231-4007, mandarinhide.com). Try one of the seasonal, barrel-aged cocktails made in charred-oak casks.

Stay: Veer from St. Pete’s traditional inns and book a room at the upscale, Mediterranean-style palace turned resort Kimpton Hotel Zamora (3701 Gulf Blvd; 888-809-1588, thehotelzamora.com). Make your way to the rooftop lounge for 360-degree views of the Gulf of Mexico and the Intracoastal Waterway.

Tampa
Photograph: Courtesy Visit Tampa Bay/Keir Magoulas

Tampa

Distance and drive time: 282mi, 4 hr

Home to the original Cuban sandwich (sorry, Miami), the largest collection of buildings once designated for the U.S.’s booming cigar industry and a multiethnic population more diverse than most cities in the Sunshine State—plus dozens of award-winning restaurants—Tampa combines the best parts of Florida’s past and present into one exciting, balmy metropolis.

Eat: Bern’s (1208 S Howard Ave; 813-251-2421, bernssteakhouse.com) has been slinging lauded dry-aged red meat in Tampa since 1956. Home to a massive wine library and legendary desserts room, this family founded and run spot delivers the full white-tablecloth steakhouse experience (every steak is served with French onion soup, a salad, baked potato, onion rings and a vegetable of the evening) plus caviar service and ample seafood entrees.

Drink: Tampa Bay boasts one of the country’s top craft beer scenes, so don’t do yourself a disservice by missing out on one of the area’s many eclectic taprooms. A cornerstone of Tampa’s craft brewing community, the original Cigar City (3924 W Spruce St; 813-348-6363, cigarcitybrewing.com) location proffers exclusive drafts, a full-service kitchen, brewery tours, merch and to-go beers from inside an actively brewing facility .

Stay: Hotel Haya (1412 E 7th Ave; 813-568-1200, hotelhaya.com) is a glittering new(ish) boutique hotel in historic Ybor City, one of only two neighborhoods in Florida to hold a National Historic Landmark designation. Named for cigar pioneer Ignacio Haya, the property serves as an architectural nod to Tampa’s storied past (the structure comprises two of Tampa’s oldest buildings), but keeps a firm grip on the present. Locally made fixtures and furnishings accent the sleek, well-appointed space, including the handblown lamps fashioned after the Chihuly pieces on display at the Morean Arts Center.

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