When most people think of road trips, they envision all-American summertime destinations like Yellowstone, Mt. Rushmore, Disneyland, and the Gateway Arch. But just because the days are shorter and the forecast is chillier doesn’t mean you need to hit the brakes on road travel. In the South, winter is an ideal time to hit the road and explore. Not only will the crowds be lower compared to summer, but the humidity has dwindled, hurricane season has dried up, and the intense desert heat has softened to blissful warmth. From Miami to San Diego, this epic road trip will introduce you to a whole new kind of winter wonderland.
Start your journey in the quintessential warm-weather winter getaway: Miami, Florida. The Magic City is at its sunniest this time of year, and before spring break sets in, it’s a relatively quiet season for hitting South Beach and snagging a table at a typically hard-to-get-into restaurant (looking at you, Yardbird). While here, be sure to stroll the art-filled streets of Wynwood, where you can also grab a beer — and beer can bread with whipped guava butter — at La Cerveceria La Tropical, shop artist merch at the Wynwood Walls store, and drag yourself to a riotous drag brunch at the always-lively R House, where platters of cayenne-spiced fried chicken are almost as hot as the queens.
Where to stay: Miami just so happens to be one of Kimpton’s most well-represented cities, where your options include the Kimpton Surfcomber Hotel, the Kimpton Angler’s Hotel, and the Kimpton EPIC Hotel.
Drive north just a few hours to the “theme park capital of the world,” where you can get your fill of whimsy and magic, while also discovering a new side of Orlando most visitors don’t see. Of all the incredible new sights and attractions in the area, the must-dos include Star Wars-themed Galaxy’s Edge in Disney’s Hollywood Studios, a Ratatouille-inspired ride at EPCOT, and some seriously decadent sweets shops in Disney Springs, like Everglazed Donuts & Cold-Brew and Gideon’s Bakehouse for half-pound cookies the size of your head. Be sure and head into Orlando proper to explore cute neighborhoods like Audubon Park and the Milk District, home to charming bars, restaurants, cafes, and boutiques aplenty. Our picks? Kadence for an omakase sushi experience, Deeply Coffee for cereal milk-infused lattes in a chic setting, and a swan boat ride on Lake Eola, surrounded by actual swans.
Where to stay: while you’re in central Florida, you won’t find a better oasis than Kimpton Vero Beach on the Treasure Coast.
Round the Gulf and make a pit stop in the always-fun city of New Orleans, where pre-Mardi Gras winter crowds are minimal and you can stroll down Bourbon Street, cocktail in-hand, without shoulder-to-shoulder traffic. Exploring the French Quarter is always a must, with essential stops for beignets at Cafe du Monde and frozen Irish coffee at Erin Rose, but don’t neglect the outlying neighborhoods, too. The Bywater is filled with pastel-toned houses, al fresco jazz and wine at Bacchanal, and breakfast gumbo at Bywater Bakery, while the Garden District stuns with centuries-old mansions, historic cemetery tours, and iconic restaurants like Commander’s Palace, where timeworn recipes like bread pudding soufflé have been fan-favorites since 1893.
Another impossibly cool city that deserves a spot on any winter road trip is Texas’ state capital. Keep things weird in Austin with a bar-crawl on historic Rainey Street (Half Step is a good option for a more chill environment, where you can actually find a patio seat and sip your pineapple daiquiri in peace), cheesy-eggy breakfast tacos at Tamale House East, worth-the-wait barbecue at Franklin’s Barbecue, and a night of androgynous dancing at Cheer Up Charlie’s, a come-one-and-all bar and club known for laser lights, organic juice cocktails, and a sprawling outdoor dance floor. Be sure and spend time in suburban Hill Country, where you can hike at Pedernales Falls State Park and spend the afternoon at Jester King Brewery for goat yoga, sour beers bursting with local fruit, and incredible wood-fired pizza.
Where to stay: The Kimpton Hotel Van Zandt is a massive stunner near Rainey Street, so you won’t have far to go after a night of bar-hopping.
Entering the Southwestern desert, buckle up for some serious fun in the sun, under bright blue skies that seemingly stretch forever. As Arizona’s largest city, Phoenix is an apt stopover for culture, cuisine, shopping, hiking, and some serious eats. Check out the Phoenix Art Museum for sprawling exhibits, manicured gardens, and a wide array of immersive Southwestern landscape portraits, then dine on the enormous patio at Ocotillo for fresh-as-can-be seasonal eats like charred sweet potatoes with tahini and avocado, grilled kuri squash in mole, and the signature mesquite-grilled chicken with chilies, local honey, and date-potato salad. UnderTow is a fun, transportive tiki bar that’ll make you feel like a stowaway on a pirate ship, and Noble Bread is a local icon for artisanal loaves and pastries. Surrounded by mountains and soaring cacti, Phoenix is also a great city for outdoorsy types, as evidenced by the awe-inspiring views atop Camelback Mountain.
Where to stay: The Kimpton Hotel Palomar Phoenix is ideally situated smack dab in the middle of the downtown fray, close proximity to everything from sunrise hikes to sunset cocktails.
Wrap up your winter road trip with a grand finale in sunny Southern California, where miles of beaches beckon and hip neighborhoods like Hillcrest and the Gaslamp teem with unique breweries, restaurants, galleries, and more. Enjoy a pint at Hillcrest Brewing Company, the first openly gay-owned brewery in the country, a stop in La Jolla for Instagrammable avocado toast at Parakeet Cafe, and sift through chic SoCal swag at Johnny Was women’s boutique. And should you find yourself at one of America’s most iconic (albeit touristy) zoos, we won’t judge. It’s all apart of a road trip done right.
Where to stay: There’s another Kimpton Hotel Palomar in San Diego, home to a sensational — and quintessentially Californian — rooftop pool bar.