Ann Arbor, Michigan
Visit in the fall for a game at the Big House or in the summer to explore the renowned city art fair. Either way, Ann Arbor is so much more than your average college town. Get your nature fix by exploring the arboretum, nosh on some Cuban-inspired street food at Frita Batidos and embark on a scavenger hunt for the tiny fairy doors built into buildings and trees around the city.
Where to stay: Stay right on campus at the Inn at the League, a university building with lots of charm.
Asbury Park, New Jersey
This funky resort town is experiencing a major resurgence at the moment. In the summer, start your morning with sunrise yoga on the Asbury Hotel’s Baronet roof space, and then head to the famous Asbury Park Beach before you do dinner and movie back on the Baronet. Want a night out? The city has a surprisingly robust LGBTQ scene (check out Paradise for a drag show) and rock music culture (the Stone Pony, aka the birthplace of “The Boss,” is a must).
Where to stay: Stay in a former Salvation Army building turned hip hotel, The Asbury Hotel.
Asheville, North Carolina
This southern city dropped in the Blue Mountains is a breathtaking little enclave for artists and hippies. Peruse the River Arts District to find something unique for over the mantel, and replenish at funky eateries like The Admiral (which transforms into a dance party post-dinner). Hike the three-mile Pisgah Trail for the best views of the city and wind down with a beer (there are more breweries in Asheville per capita than in any other U.S. city).
Where to stay: Instead of merely visiting the famous Biltmore House, why not stay there?
This cowboy town is seeing lots of development in a very short amount of time; but locals are committed to maintaining its original character. The outcome? Plenty of buildings dating back to the 1890s, galleries, shops, restaurants and coffee shops (lots of coffee shops) to peruse. Meander around Main Street’s independent book shops, and then splurge on a pair of custom kicks from Carter’s Boots. And if you want to get your Ansel Adams on, take a photography workshop at F11Photo (just don’t forget to pack your camera when you hike Drinking Horse Mountain).
Where to stay: Designed to help you get the most out of southern Montana, The LARK is all about bringing old and new Bozeman together.
Beer lovers may flock to Asheville or Seattle, but Cincinnati is a treasure trove of brews. In fact, it’s home to more than 40 breweries with its very own beer trail: The Brewery Heritage Trail. Once you get your buzz going, make sure to save ample time for the Over-the-Rhine district, one of the largest, most in-tact urban historic districts in the U.S. Oh, and it’s got some really great food, too.
Where to stay: Right across the Ohio River is the waterfront Hotel Covington. Sure, it’s technically in Covington, Kentucky, but its rates will make the short trek so worth it.
Charleston, South Carolina
With its waterfront promenades, iconic architecture and cobblestone streets, this seaport city is brimming with things to do over a long weekend—and much of it involves food. Make sure to make a fancy dinner reservation at FIG, Husk or the Charleston Grill. And no trip to Charleston would be complete without a visit to nearby Boone Hall Plantation—where countless movies have been filmed. And if you have extra time on your hands, island hop to Kiawah Island, where you’ll undoubtedly stumble upon your own private beach.
Where to stay: Charleston is all about elegance. So do it up in style at the Belmond Charleston Place.
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Columbia, South Carolina
If Charleston is Marcia Brady, Columbia is Jan. But that’s fine by us. As Soda City experiences its urban revival, we’re fine keeping this best-kept secret to ourselves. With old gems like the Robert Mills House & Gardens and Lula Drake, a cozy, historic wine bar, this super-walkable, charming city feels like a small-town getaway within a big city.
Where to stay: The brand-new Aloft Columbia Downtown is walking distance to everything.
Litchfield Hills, Connecticut
One word: antiquing. From estate sales to flea markets and barn-inspired stores that would make Chip and Joanna Gaines’ hearts flutter, a weekend in Litchfield means discovering hidden gems. Need a break from the dust? Take to the skies and get a bird’s-eye view of it all from a hot-air balloon.
Where to stay: The 18 luxury cottages at Winvian Farm each have their own unique spin—like a whimsical-chic tree house, a refurbished helicopter and a nautical lighthouse.
Even if you don’t make it there for the famed Kentucky Derby, there’s so much do in Bourbon County, including, of course, the Urban Bourbon Trail, where you can spend a buzzy afternoon hopping between distilleries. Of course, there’s also baseball, bluegrass and mint juleps (c’mon, you have to have one here).
Where to stay: Art lovers: You must try the 21c Museum Hotel in downtown Louisville.
From honky-tonk bars up and down Broadway to the Grand Ole Opry, there’s really no escaping live music when you’re in Nashville. If you want real-deal country, head to Robert’s Western World. Want to spot the next big thing? Make sure you get to the 90-person venue at Bluebird Café early. Bring home an epic keepsake from Hatch Show Print, the letterpress design shop known for its iconic posters.
Where to stay: For some straight-up Southern hospitality, The Hermitage is a must (they’ll even walk your dog for you).
RELATED: Your Guide to Nashville, Tennessee
Palm Springs, California
Desert sunsets, mountain views and perfect weather—it’s no wonder this SoCal city has been an old Hollywood escape for years. Sip on a martini at Johannes and be transported back to the 1950s, take an architecture tour of the mid-century modern homes and, most importantly, enjoy the weather poolside.
Where to stay: The hotel scene in Palm Springs is legendary, and the Saguaro Hotel is a fresh take on a classic, replete with lots of bright color, a pool and mountain views.
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The sleepy town across the Golden Gate is a wonderful little reprieve from the hustle and bustle of SF. Book a walkabout in the olive tree fields at McEvoy Ranch (save time for an olive oil tasting!); eat duck confit cassoulet at The Drawing Board and follow it up with a cocktail at Barber Cellars, Petaluma’s first tasting room for small-production, single-vineyard wines. Mmm.
Where to stay: The revamped Art Deco Hotel Petaluma, which dates back to 1924.
RELATED: Petaluma’s the New Hot Spot (We Promise) and Here’s Where to Go
Philly may be stoked in history, but it’s currently booming, and no, we’re not just talking cheesesteaks or the Liberty Bell (although, hey, nothing wrong with either). The thriving food scene sates even the snootiest East Coast foodies. (OK, we’re looking at you, New Yorkers.) From classics like the tomato pie at Marchiano’s Bakery to newbies like Danlu, a smart-looking Taiwanese street food restaurant, there’s no shortage of interesting things to taste or do. Book your rezzies accordingly.
Where to stay: Aloft Philadelphia Downtown blends the city’s rich history with contemporary vibes.
The dream of the ’90s is alive in Portland! Well, at least according Fred Armisen and Carrie Brownstein. But it’s time you checked out this hipster paradise for yourself. Feast on craft coffee, cider, doughnuts and all the farm-to-table cuisine you can stand in line for (we kid, we kid). Beyond the city’s quirky culture, you’ll also have to make time to explore the beautiful Pacific Northwest landscape.
Where to stay: Get the best of both worlds at the River’s Edge Hotel, right at the junction of downtown Portland and the tranquil Willamette Valley.
San Antonio, Texas
While all the bachelorette parties are heading to Austin, you should make way to this riverside city (even if all you recall about this Texas town from history class is “Remember the Alamo!”). Start with the River Walk. It may be touristy, but we’re suckers for the water taxis that let you hop between food, drink and shopping. There’s also the Pearl District, the 1881 brewery turned sprawling development that’s become a trendy hot spot with live music, farmers markets and so much more. And of course, nothing beats a picturesque picnic in Hill Country.
Where to stay: For rooftop pool and complimentary Electra cruiser bikes, you should most definitely stay at Hotel Emma.
Santa Fe, New Mexico
It’s the city where art meets nature. Hike amid the aspen trees (which turn a gorgeous orange come fall) and meander through the city’s countless galleries, sculpture gardens and artisan turquoise shops. If you’re a fan of George R.R. Martin, or the avant-garde, you must take time for Meow Wolf, the multilevel interactive art museum filled with VR, audio engineering and a strong dose of mystery.
Where to stay: For a historic and iconic getaway, try the Inn and Spa at Loretto.
Sure, there’s lots to do in this glorious West Coast region. But we all know why you’re here: wine. Sip your way through the city at tasting rooms like La Crema or the 140-year-old cellars at Simi. Make sure to make time for—drumroll, please—more wine at Sonoma-Cutrer Vineyards, where you can drink wine and play croquet on the courts.
Where to stay: Want a bargain? This tiny house-style cottage is a Sonoma steal priced at $140 a night.
St. Petersburg-Clearwater, Florida
Sure, everyone’s going to Miami, but if you’ve only got the weekend, why not try to beat the crowds? This Gulf Coast city has everything you could want in a Florida vacay: perfect weather, gorgeous beaches and some great indoor activities to keep you busy when you need a break from the sun—the Salvador Dali Museum or vintage shopping, anyone?
Where to stay: Go for classic at The Don CeSar, aka the “pink palace.”
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