The best 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 epicenter of privilege and luxury. Palm Beach’s riches are there for the taking—so long as you have a high tolerance for lunching ladies, pastels and general clichés of wealth.

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 bar inside The Brazilian Court Hotel (301 Australian Ave; 561-655-7740, thebraziliancourt.com) looks like the backdrop of a Great Gatsby party, full of deeply cushy leather couches, Sausalito tiles and a wooden tray ceiling that some poor sap must have to oil regularly. Chef Daniel Boulud is behind the happy hour menu (4-6pm), with high-brow items like Crispy Duck Pastilla. The cocktail menu is as upscale as the surroundings: We'd suggest the white cosmopolitan, with elderflower and white cranberry, cooled off with an ice sphere holding an orchid.

Stay: A Nantucket socialite named Elizabeth T. Ludwig opened the first White Elephant in the 1920s, establishing a chic spot for vacationing industrialists. The hotel’s bougie style was exported to Palm Beach in 2018, with White Elephant Palm Beach (280 Sunset Ave; 561-832-7050, whiteelephantpalmbeach.com) occupying a rehabbed historic property that now exudes all the marbled glamor you expect on this island of multiple billionaires.

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.com) brings 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.

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 to taste one of the city’s most creative seafood menus, featuring comfort food classics like 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: Southernmost Beach Resort (1319 Duval St.; 800-354-4455, southernmostbeachresort.com) at the oceanside end of Duval Street dots its three pools with palm trees and private cabanas, each with a specific vibe, from a more chill adults-only to one that hosts live entertainment. The resort becomes a de facto HQ for nearby Key West events and has hosted the Pineapple Pool Party during the Key West Songwriters Festival and a five-course dinner during the drawn-butter extravaganza that is Lobsterfest.

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 paired mains of which the classic cacio e pepe bucatini with sheep’s-milk cheese is simply phenomenal.

Drink: Sidebar (475 5th St S.; 239-272-2167, facebook.com/sidebarnaples) lives up to its name with an entrance on the quiet side of a three-story building at the corner of Fifth Avenue and Fifth Street. Mid Century style awaits inside with tufted leather couches and lots of blue velvet. Cocktails here, though, are far from just the old standards, with creative combos like the Queen Pea, served straight up with snap-pea-infused Sochu, Génépy, lemon and almond.

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: 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.

Distance and drive time: 230mi, 3.5hrs

The sandy shores as white and powdery as nose candy (not that we’re endorsing such things) are reason enough to traverse the Florida peninsula. But it’s also Sarasota’s quirks that make it a fascinating spot for a weekend trip, with a legit Amish enclave in the center of town, a vibrant performing arts scene and Ca' d'Zan, a Moorish-styled mansion that serves as a museum to its former circus magnate owner. How’d all that come together in one place? We don’t know, but we’re glad it’s not far away.

Eat: A retired circus performer opened Main Bar Sandwich Shop (1944 Main St.; 941-955-8733, themainbar.com) a half-century ago in downtown Sarasota, and it’s thoroughly a trip back in time, the walls covered in circus photos that capture the days when Ringling’s stars would winter here. That's all good and charming, but the reason to come is the Italian, a muffuletta-like combo with a garlicky oil that'll drip to your elbows.

Drink: They say The Gator Club (1490 Main St.; 941-366-5969, thegatorclub.com) served as a speakeasy during Prohibition, and since then the rocking party has not slowed one bit, with bands and maybe a burlesque show on stage, while upstairs there’s pool tables in a more chill lounge. What are you ordering? Literally anything, from a decent old fashioned to a pint with a sidecar.

Stay: Sarasota is home to a Ritz and plenty of other luxe chains, but embrace quirky at the Burns Square Historic Hotel (531 S Pineapple Ave.; 941-888-4884, burnssquare.com), just a couple blocks from downtown in a neighborhood full of well-kept homes that date to the city’s founding.

Distance and drive time: 282mi, 4 hr

Home to the original salami-spiked 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: Boulon Brasserie (1001 Water St.; 813-768-9988, boulontampa.com) is the upscale Frenchified restaurant in the Water Street development/entertainment district that rose up recently in downtown Tampa, and the heavily gilded digs are as classy as the dishes coming out of the kitchen. After crushing blue crab beignets and duck confit, be sure to save room for desserts created by the Milk Bar alum Summer Bailey, who infuses many of her sweets with an addictive hint of salty.

Drink: Tampa Bay boasts one of the country’s top craft beer scenes, so don’t miss 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.

Stay: Hotel Haya (1412 E 7th Ave; 813-568-1200, hotelhaya.com) is a glittering boutique hotel in historic Ybor City. 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 hand-blown lamps fashioned after the Chihuly pieces on display at the Morean Arts Center.

Distance and drive time: 240mi, 3.5 hours

There are times when a trip to Orlando's theme parks is in order, like, say, if you want to keep the kids from emancipating themselves. But that doesn't mean you'll need to stay in the soulless, tourist hell that is Orlando’s International Drive. Instead head west to Winter Garden, a legit cultural enclave with a dining and boutique shopping scene downtown.

Eat: Chef Ryan Freelove spent a couple of years selling soups and dressings at farmers’ markets before opening Market to Table (146 W Plant St.; 407-395-9871, market2table.com), so it makes sense that he still relies on products from local farms. That means what's on offer here is very seasonal, but expect things like bone marrow with pickled onions, Spanish octopus with fingerlings and house-made tagliatelle with locally raised chickens.

Drink: We’d go to Crooked Can Brewing Company (426 W Plant St.; 407-395-9520, crookedcan.com) simply for the taproom, the pizzas and the beers that keep winning all the awards. But the kicker is the outdoor area, full of tables shaded by the massive arms of a live oak, where a chill party vibe often pops up on the weekends.

Stay: The Oakland Manor House, an old-school B&B, occupies a shady spot on the shores of Lake Apopka, offering a quiet respite from the craziness of O-town. The inn’s sleepy neighborhood gets intersected by the West Orange Trail, ideal for a walk or bike ride to the Saturday Farmers’ Market in Winter Garden.