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A key component to the mastery of a skill is knowing when to break the rules. As its name implies, Jovanina’s Broken Italian breaks away from the traditional rules and expectations of Italian cuisine with the measured confidence of a master. Owners Jennifer and Jake Linzinmeir bring years of restaurant experience, both in the kitchen and in management, to Jovanina’s, which allows them to find an approachable balance of new flavors and classic dishes to the menu. The airy ground-floor space feels festive, with whitewashed brick walls along one side and a bar running the length of the other; a downstairs wine-bar dining area has a quieter, more intimate vibe. Try any of the handmade pasta specials or go with the favorite: a brick-oven pizza topped with fennel sausage, smoked mozzarella, and caramelized onions.

Once the hip newcomer, this craft cocktail lounge is now a King Street veteran that attracts a more mature crowd than the line-up-outside adjacent clubs catering to the college set. Locals meet here for half-price happy hour (Wednesdays feature bourbon) and before shows at the Charleston Music Hall nearby. The stock of spirits is impressive, as are the intricate ways they’re mixed, like a “Macho Man Dandy Savage,” with house-infused dandelion gin, honey, and yellow Chartreuse. The mixologists here have a history of winning local bartender competitions. Complementing the flavors are the gorgeous environs in an historic building that features exposed beams, leather furniture, and a swanky rooftop garden that’s a welcome respite just off the buzz of King Street below. It all sits atop The Macintosh, chef Jeremiah Bacon’s stunning seasonal fare restaurant that shares a mutual owner.

Orlando is known for great Asian eats, and this sweet little Thai spot in Winter Park stands apart for its stylish vibe and rainbow range of iced and hot teas and desserts. KrungThep is the Thai name for Bangkok, but much of the menu skews fusion-style, with items like pesto chicken sandwiches and satay sandwiches and toast-style desserts topped with everything from condensed milk and homemade coconut ice cream to Nutella, matcha, and organic honey. Tea-lovers are in heaven here, with herbal, black, and white loose leaf varieties galore. The black and white decor scheme is both blatantly Instagram-able and cozy and inviting. For a quiet chat with a friend or a self-care moment alone, you can’t go wrong while taking a break to recharge here.

Right on Key West’s famous Sunset Pier and next to Mallory Square, Ocean Key is at the center of the action, proven by the flocks of tourists who descend on the pier every evening at sundown. Inside the resort, the contemporary rooms are decorated in tropical colors like bright lime and turquoise, and have bathrooms with rainfall showers and whirlpool tubs and private balconies with views of the Gulf of Mexico or buzzy Duval Street. The angular pool is surrounded by cabanas and day beds; grab a ringside seat for the daily fashion show at Liquid, the kicking poolside bar. Prefer a quieter experience? The spa has a full range of treatments and packages that lean heavily on Asian traditions and ingredients, from Balinese massage to a Javanese rice-and-turmeric body scrub.

Austin has established itself as a foodie destination on par with New York and Los Angeles. Now, it also has a hotel that’s worthy of its rebirth as a capital of cool. At The LINE, the setting is as pretty as the young things who stay there with their stylish pets. The midcentury building houses 428 rooms and suites inspired by the Lone Star landscape, with headboards that evoke desert canyons, blue linens and rugs that nod to Lady Bird Lake (which many of the rooms overlook through expansive floor-to-ceiling windows), and lighting that looks like fireflies in the night sky. The place to be seen is Arlo Grey, where Top Chef winner Kristen Kish serves a menu inspired by her childhood, travels, and Central Texas ingredients—that is until the rooftop bar debuts in fall 2018.

Situated off the eastern shore of Long Island, The Chequit is old school in an elegant way. The hotel occupies a big white building, surrounded by grassy lawns, impeccably maintained hedgerows, and towering deciduous trees, and features bright, homey rooms, complete with large windows that let in plenty of natural light. While all the rooms have been refurbished, those in the main house retain much of their original architecture, lending them a certain vintage charm. The Chequit operates on a bed-and-breakfast model, and guests can either take their morning meal in the lobby or opt to have a lighter option sent straight to their room. While the target audience here is weekenders seeking an escape from New York City, the hotel is also a popular spot for weddings and retreats, with two meeting rooms and full catering services available from on-site Red Maple Restaurant.

A larger, more luxurious alternative to an inn-style getaway, the ocean-facing Gurney’s Montauk Resort offers gorgeous views, plush accommodations, and top-notch amenities, including a whopping 2,000 feet of private sandy beach. The spa is the star attraction and includes a Finnish sauna, steam room, Roman bath, and saltwater swimming pool, all of which are only open to guests to maintain a quiet, exclusive ambience. Other property highlights include a salon, fitness center, and selection of restaurants, ranging from Scarpetta Beach (which serves Italian cuisine) to Tillies (a more casual bistro with hearty American fare and brunch specialties on weekends). Not surprisingly, the guest rooms and cottages are especially luxe, with lovely wooden floors, walk-in rain showers, and big windows with sweeping sea views.

Set on almost four acres in the Catskill Mountains, a couple of hours outside of New York, The Villa at Saugerties is a tranquil four-room inn surrounded by stunning gardens, complete with weeping willows, streams, and a lily pond. All four rooms here are impeccably maintained, with gas fireplaces and lovely bathrooms complete with Moroccan tiling. While the Villa’s pleasant grounds and the 40-foot swimming pool are enough to keep guests from leaving the property, there’s also plenty to do in the sylvan surrounded, from hiking and mountain biking on local trails to touring the myriad quaint old towns for which the Hudson Valley is known. The gourmet breakfasts here cooked with local ingredients get rave reviews, as does the warm hospitality from the inn’s owner-operator couple, Amanda and Joe.

Although Troutbeck’s current incarnation only opened in 2017, the estate property has stood in the Upstate New York town of Amenia for considerably longer. It started in 1765 as an inn and tavern and, over the years, has hosted some of America’s most celebrated literary greats, from Mark Twain to Ralph Waldo Emerson. While the historic home now includes plenty of modern comforts, it also retains many of its old-fashioned features, from the wood paneling in the cozy living room to the enchanting Walled Garden, which was constructed over a century ago to house the then-owner’s collection of clematis. The property also has a lovely outdoor swimming pool, tennis courts, an elegant ballroom that’s popular for weddings, and a range of stylish rooms and suites, many with big windows, four-poster beds, and deep soaking tubs.

Sitting on 40 acres in the quaint town of Stone Ridge, Hasbrouck House is a lovely boutique getaway, featuring 20 one-of-a-kind rooms spread out over three structures. Rooms are bright and homey, with wooden floors and plush beds. Some even feature vaulted ceilings, stone fireplaces, and deep, freestanding bathtubs. Although it’s not a spa retreat, Hasbrouck House does offer a variety of massages that can be enjoyed either in a cozy treatment room or your very own suite. For many guests, however, the highlight of a weekend here is dinner at on-site restaurant Butterfield, which offers a seasonal menu inspired by fresh produce from the Hudson Valley. Come in the summer and you’ll also have access to the 55-foot-long swimming pool, nightly bonfires, and outdoor movie screenings and concerts.

From its location in Denver’s Union Station, Mercantile Dining & Provision makes delicious and nutritious meals accessible to commuters and travelers passing through. This is the second eatery by Alex Seidel, a committed restaurateur who purchased a farm east of Denver to better understand the journey food takes from field to plate. The on-site market offers artisan-made provisions from spices and pickled beets to jams and jellies to coffee and potato chips. In the dining room, chef and partner Matt Vawter serves dinners so good you may miss your train—the spicy mussels (served in a tomato-butter broth perfect for mopping up with bread to console yourself after the shellfish and fennel sausage are gone), the housemade pastas, or the rotating selection of fire-roasted meat and fish entrees, can make the most fastidious traveler lose track of time.

Though it doesn’t have the same rustic charm as the Bright Angel or El Tovar lodges—its neighbors on either side—the 1960s-era Thunderbird Lodge hasn’t lost that fun Mad Men vibe. Just yards away from the South Rim, it looks more like a college social sciences building from the outside, but the 55 updated rooms are comfortable and spacious, with geometric-patterned rugs and headboards, marble-topped furnishings, and stone-tiled bathrooms, plus creature comforts like satellite TVs, Keurig coffeemakers, and in-room refrigerators. Many have decent views of the canyon—a steal at only $20 more. And while there’s no restaurant on site, dining options at El Tovar, Bright Angel, and the rest of the village are only steps away. Best of all, the Rim Trail is right outside your door.

Chances are you’ve seen Maria Pinto’s works at some point in recent years—she’s known for dressing the likes of First Lady Michelle Obama, Oprah Winfrey, and Brooke Shields. That fan base is only growing with the opening of her West Loop Style Studio, where women can shop M2057 by Maria Pinto, a ready-to-wear collection inspired by urban architecture and design. Created for the time-pressed but fashion-forward woman, Pinto’s pieces marry runway ideas with a low-maintenance aesthetic (the upscale fabrics might be imported from Italy, but they’re also machine-washable and wrinkle-resistant—perfect for travel). In addition to plenty of day-to-night options like dresses, skirts, tops, and pants, the boutique also carries belts and jewelry by outside artists, curated by Pinto.

Whether it’s brunch, happy hour, or date night, Barcelona Wine Bar’s shared-plate dining and drinking experience is a D.C. socialite staple. Mingle over pitchers of red wine sangria with a rotation of farm-to-table tapas, including a light spinach and manchego frittata with a bacon crunch at brunch and a spicy eggplant caponata with sweet pepper, basil, and parsley at dinner. People-watch from the garden patio or gather inside the rustic-chic dining room, where the Jamon Mangalica ham being hand-sliced will inspire you to order the charcuterie. After crisscrossing arms with your dining partners to share bites of elevated, familiar flavors, finish on a comfort-food high with a spoon fight over their luscious flourless (gluten-free) chocolate cake. You can do it all again at a second location on Wisconsin Avenue in Cathedral Heights.

Named 2016’s best new restaurant in America by Bon Appétit, Staplehouse is still Atlanta’s hardest reservation to score. Husband-and-wife team Ryan and Jen Hidinger dreamed up the restaurant after a series of successful supper clubs, which they hosted in their own home. Before they could open, however, Ryan was diagnosed with stage IV gallbladder cancer. Atlanta’s restaurant community rallied around the couple, raising money for Ryan’s treatments and eventually founding the Giving Kitchen charity. Eventually, the Hidingers leased a space and brought in Ryan’s sister Kara and her boyfriend, Ryan Smith, to run the restaurant. Ryan passed away in 2014 but his legacy lives on at Staplehouse, where Jen now serves as the business manager. While Ryan’s story is at the heart of the restaurant—a portion of the proceeds goes toward his charity—it’s Smith’s seasonally inspired menu that has kept Staplehouse on top.