America’s Best Long Weekend Getaways

For a low-key romantic weekend away, the art-centric mountain town of Asheville won’t do you wrong. Perhaps the crowning jewel of the trendy yet traditional city, the Biltmore Estate simply isn’t to be missed. The 250-room Gilded Age chateau sits on 8,000 acres of highly-curated gardens and meadow (all designed by the very guy behind NYC’s Central Park, Frederick Law Olmsted) with the Blue Ridge Mountains serving as a super casual backdrop. Peeling yourself away from the largest mansion in the U.S., you’ll get your night’s sleep at The Windsor Boutique Hotel, a homey 14-suite rustic stay right in the heart of downtown. End your mini-retreat with brunch at Cúrate, a buzzy tapas-inspired restaurant with crowd pleasers like honey-drizzled fried eggplant and traditional tortilla española.

Kimpton Hotels know how to turn on the quirk, and the historic Palladian is no exception. Guest rooms at the Belltown spot work screenprinted Mr. T and David Bowie pillows, vintage maps, and smart brass fixtures into an otherwise classic mix. Two blocks away, you’ll find the famous Pike Place Market, your go-to place for quick bites, while luxe sit-down meals are best at The Butcher’s Table, which delivers with a raw bar, inventive sides, and every cut of steak known to man. To walk it all off, head for exhibits at Chihuly Garden and Glass, an IG goldmine dripping in galleries of vibrant glass sculptures—the center of which is a suspended red, yellow, and amber floral piece that lives in the Glasshouse.

Bed down at the ultra-quirky Freehand Miami for a stay packed with vintage travel ephemera, mod furniture (making use of a ROYGBIV palette), and a social courtyard with a pool, bocce, yoga, and art classes. Dinner is to be had at Byblos, a design-savvy, family-style Eastern Mediterranean joint that serves up duck kibbeh, Persian fried chicken, and fattouche, in an impossibly bright (and chic) dining room. Art is all around in the Magic City, and to see the best of it, you don’t need a ticket or a proper tour—simply take yourself on a self-guided walk around Ocean Drive’s Art Deco and Art Nouveau buildings, making sure to stop for photos at favorites like Hotel Breakwater South Beach, the Leslie Hotel, the Essex House Hotel, and The Tides South Beach.

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The boutique Palomar Philadelphia deftly spins an eccentric take on a classic American design scheme with neon presidential portraits, rainbow-hued busts, and plush velvet seating. Take an hour or so to hit Philadelphia’s Magic Gardens, a museum, outdoor art installation, and indoor gallery from mosaic artist Isaiah Zagar, which takes up half a block on the once-dilapidated (and now handsomely revitalized) South Street. Or swing by the Barnes Foundation to see a stunning display of French impressionist and post-impressionist paintings. For some Philly history that isn’t the Liberty Bell, you can check out Eastern State Penitentiary—a massive, fortified prison that once held Al Capone—on an audio-guided tour narrated by the one and only Steve Buscemi. Afterwards, skip the over-hyped cheesesteaks at dueling shops Geno’s and Pat’s, and head instead for the Reading Terminal Market, where you can nom on pad thai, oyster sliders, and sweet dessert crepes all under one roof.

A weekend is all you need to see the very best of Texas’s coolest city. Kick it off with a locals-only brunch at Elizabeth St. Cafe, a chic French-Vietnamese boulangerie where coconut water and preserved tangerine margaritas are served in Chinese takeout containers. Newer spots on our radar include the Southern-inspired Colleens Kitchen, Pool Burger (we love the Blue Hawaiian, topped with grilled pineapple slices, bacon, crumbled blue cheese, and Thousand Island dressing), and Aviary Wine & Kitchen. For some retail therapy, head to South Congress for an afternoon at the boutiques; United Apparel Liquidators is the place for designer couture (Balenciaga, Rag & Bone, Givenchy, to name a few) at bargain basement discounts. Don’t leave the city without going for a dip at Barton Springs Pool, the aquifer-fed swimming hole of choice where a young Robert Redford learned how to swim.

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You can’t go to Chi-town without stopping by the Art Institute of Chicago. We’d say the same about leafy Garfield Park Conservatory, built on nearly five acres in 1906 and often referred to as “landscape art under glass;” the Chicago architecture river cruise; and, of course, Wrigley Field. (Yes, all of these are touristy, but so worth it.) You could spend an entire weekend eating your way through this city. Some of our favorite spots to hit up now include the Michelin-starred brewpub, Band of Bohemia; the wildly popular Korean-American restaurant, Parachute (book early!); and the British-inspired Owen and Engine, which serves one of the finest burgers in town. As for where to stay, we’re digging Hotel Zachary, with its stunning grand staircase and knockout views of Wrigley Field from almost every room.

Just north of Denver, an outdoorsy paradise where locals are tanned, toned, and likely just back from a trail run awaits. Catch up with the best of them on the one-mile First Flatiron trail, which winds through Boulder’s iconic sandstone slab rock formations. Break for afternoon tea in an intricately carved wooden teahouse at Boulder Dushanbe Teahouse originally made in Tajikistan—it’s a highbrow prelude to an afternoon tour of Avery Brewing, home to the hoppy India Pale Ale. After a couple of brews, head back to your hotel (there’s the funky, low-key Basecamp and more upscale St. Julien Hotel and Spa) for a quick nap before dinner at the ever-popular northeastern Italian-inspired restaurant Frasca Food and Wine run by Chef Lachlan Mackinnon-Patterson.

In the land of beignets, po’ boys and kicked-up cajun cuisine, a weekend in NOLA is all about EATING. Start the gluttony with the classic creole-inspired brunch (and 25 cent martinis!) at Commander’s Palace—the wild Louisiana white shrimp stuffed with spicy tasso ham, Crystal hot sauce, pickled okra, and pepper jelly is a must. And we can’t leave out classics like Cafe Du Monde’s famous deep-fried pastry, Bon Ton Cafe’s jambalaya, and Bevi Seafood Co.’s peacemaker po’ boy full of fried shrimp, swiss cheese, and roast beef gravy with a side of seafood gumbo. Newcomers worth checking out include Josephine Estelle, the Italian osteria at the Ace Hotel. Alternatively, skip all of that and go from breakfast to lunch to dinner at the Roch Market food hall. You’ll want to pack those fat pants.

Warning: A trip to Savannah is highly caloric. But if you don’t indulge, you’re not doing it right. The line runs down the block for Mrs. Wilkes Dining Room, for very good reason: the fried chicken, candied yams, and macaroni and cheese are so good, you’ll want to get in line all over again for dinner. Explore the city’s art scene at the various galleries around City Market on your own or sign up for a tour on the second Saturday of every month. History buffs can learn about Savannah’s past at the 1868 Mercer Williams House, the former home of Jim Williams and the site of the killing of Danny Hansford in May of 1981 (remember, Midnight in the Garden of Good and Evil?). It’s also worth checking out the iconic Bonaventure Cemetery, dripping in Spanish moss and rumored to be full of ghosts—you can shake off the heebie-jeebies with a jalapeño margarita at the 18th century Olde Pink House.

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Of course, you’ll want to hit the beach in San Diego. La Jolla Cove is our personal favorite, with verdant grass that leads to craggy cliffs, but there’s so much more to do in this SoCal city. Wander the 15 (!) museums at the 1,200-acre Balboa Park, hike to the lagoon at Torrey Pines State Natural Reserve, and feast on some of the best Mexican food north of the border at Lucha Libre Gourmet Taco Shop (we love the steak, shrimp, avocado and chipotle taco).

Portland has a reputation for being the Brooklyn of the West—which isn’t entirely unfounded, given its profusion of microbrews and macro-beards. Your first stop: Ned Ludd, where almost everything on the menu (local rabbit and roasted radishes, or chocolate chip cookies in a cast iron pan, for example) is cooked on a wood fire. Hike through the rainforest to feel the spray of the 627-foot waterfall at Multnomah Falls, just half an hour from downtown Portland. Leave time for a trip to peruse the two million-some volume at Powell’s City of Books, a local favorite on Burnside St.

Frank Sinatra, Dean Martin, Elizabeth Taylor — a who’s who of showbiz has long found solace in Palm Springs. Today this desert oasis is the perfect mix of modern and kitschy which attracts a hip L.A. crowd. Spend an afternoon wandering the Uptown Design District, where eye-catching boutiques (we love the Midcentury housewares at Christopher Anthony) are joined by retro-chic restaurants and bars. Bootlegger Tiki, Palm Canyon Drive’s mixology-centered newcomer, has a 12–2 a.m. happy hour, kitschy luau-themed décor, and hangover-worthy cocktails (we love the cheekily-named Mango Unchained.) If live music is what you seek, check out Melvyn’s, the storied supper club-style hangout once frequented by Ol’ Blue Eyes himself.

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The 12-square-mile atoll sits between the tony North Fork and the Hamptons but feels a hushed world away (more than a third of the area is fiercely protected by the Nature Conservancy). Here, it’s all about unwinding, from the golden-sand beaches and hiking paths to farm fresh produce and sunset cocktails. The island’s newest place to bed down is Chequit Inn, with 37 shabby-chic rooms, C.O. Bigelow toiletries, and complimentary breakfast. For dinner, don’t miss the Montauk pearl oysters and lobster pot pie at Vine Street Café (or pick up goodies to go at the food market out back).