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Beaver Creek’s credo is “Not exactly roughing it,” and Beano’s Cabin—tucked up on the ski hill itself—is a fun way to do dinner in any season. In the winter, you can arrive at the restaurant courtesy of an open-air sleigh; in summertime, you can take an hour-long horseback ride, a tractor pull, or a 10-minute shuttle van. Once on-site, adults enjoy a five-course menu, and kids under 13 have the option of a simpler three course-meal, featuring Rocky Mountain classics like roasted venison and Colorado lamb. As expected, being up on the ski hill makes for a beautiful view no matter the time of year, although the fall is particularly stunning. (Reservations required.)

Surprisingly, great cocktails and an ocean breeze can be hard to find in San Diego, which makes JRDN at the Tower23 Hotel somewhat of an anomaly. It may be a scene—there are bouncers at the door, and the 70-foot-long wave wall would be more at home in Miami—but the wind-protected patio is practically on the boardwalk, offering great views of Crystal Pier and surfers catching waves. On warm evenings, drinks like the cava-based Raspberry Sparkler and the spicy chili-mango margarita make the experience even sweeter. JRDN’s happy hour (Mondays–Fridays, 4 p.m.–6 p.m.) offers discounted beer, wine and sake and coincides with the sunset for much of the year, making it a prime time to score a seat outside.

One of Maui’s best hikes, this trail climbs 800 feet through the lush Kipahulu area of Haleakala National Park. Half a mile from the visitor center, an overlook provides sweeping views of the gorge and the almost-200-foot-long “horsetail” of Makahiku Falls. Continue on past a sprawling banyan, stopping to marvel at the sunlight trickling through the dense bamboo forest. Here, you’ll also find the even more dramatic cascade of Waimoku Falls, which plunges 400 feet down a sheer-walled lava amphitheater. If you’re wary of tackling the four-mile round-trip hike by yourself, know that park rangers offer guided tours every Sunday at 10 a.m. Reservations are available at 9 a.m. a week ahead of time.

A classic New England bed and breakfast with a boutique hotel vibe, the Union Street Inn is housed in an impeccably maintained 1770 whaling captain’s home just off Main Street in downtown Nantucket. A short walk from the Hy-Line ferry and harbor, the inn has a convenient location in town (including parking, a huge perk on the island) and can also outfit guests with beach gear for a day on the sand. A quintessential gray-shingled exterior contrasts with the bright blue chinoiserie patterns and crisp white Frette and Matouk linens in the inn’s 12 immaculate rooms. Union Street’s cherry on top is the made-to-order gourmet breakfast, which might feature fresh peach cinnamon rolls or homemade carrot cake, depending on the season.

Quinto La Huella is the second location of arguably Uruguay’s most famous and best restaurant, the Parador La Huella in the tiny resort town of José Ignacio. On the fifth floor of the East, Miami, hotel, the eatery uses a wood-fired parrilla (grill) and oven to cook nearly everything on the menu. The dining room is wrapped in wood, and the outside dining area is a garden oasis with leafy foliage, great music, and a homey vibe. The burrata, served with fresh figs, prosciutto, and walnuts, is a standout starter, and don’t forget to order smashed potatoes, which are served as they are in Uruguay: The potato is grilled over the fire and smashed right before serving, to retain the natural texture of the vegetable.

Bookstore Bar & Café combines two of life’s great pleasures: books and booze. This hotel bar focuses on scotch and whiskey (over 130 varieties), though they also serve up carefully made craft cocktails; we liked the the Rum Daisy (light rum, lemon, house-made grenadine). At happy hour, you can nibble on small plates with charcuterie, cheese, or fried padron peppers, too. And if you see a book you like, they’re all for sale.

Inspired by vibrant Southeast Asian night markets, D.C. chef Erik Bruner-Yang (of Toki Underground fame) and D.C. streetwear mogul Will Sharp created a sleek, two-story indoor/outdoor space that’s part menswear store, part café and restaurant. The first level is all about shopping, and the floor is lined with glass-encased displays featuring Sharp’s clothing line, Durkl, as well as a library full of designer sneakers. Upstairs, sip locally roasted Vigilante coffee while snacking on Frenchie’s pastries and desserts. The best part, though, is when you step onto the patio and take a seat at the open kitchen serving up Yang’s blazing hot and flavorful Cambodian and Taiwanese cuisine. Don’t miss out on the American Wagyu tartare, the Khmer tamarind salad, the steamed pork bao buns, and zha ji pai (Taiwanese fried chicken).

Owned and operated by college pals Thomas Boisvert and Kathleen Davis, this inviting H Street spot pairs an eclectic global list of more than 30 wines by the glass (including a few on tap) with well-chosen nibbles like hearty bruschettas and build-your-own grilled cheese sandwiches. Creative offers like “Heavy Pour Mondays,” where one-third of a bottle fills each glass, and their nightly “Standby Flight List,” a five-wine sampler for only $15, have made the Pursuit a local favorite.

With soaring 10-foot ceilings and sprawling 700- to 1,200-square-foot configurations, the one- and two-bedroom accommodations at Twelve Midtown are more like modern apartments than hotel rooms. Each features a contemporary neutral-hued color scheme and comes with a full kitchen outfitted with stainless-steel appliances, plus separate dining and living rooms to encourage living like a local. But a few hotel perks made the cut, including a Starbucks in the lobby, a seasonal rooftop pool, and a full-service, 24-hour concierge desk to help you make the most of your visit—this is vacation, after all. There’s also an all-day restaurant serving classic Italian fare, including pizzas, pastas, and vegetable-forward antipasto.

After strolling Storm King Art Center or DIA Beacon, Tarry Lodge is the perfect stop on your way back to New York City. Mario Batali opened it up as a neighborhood restaurant for the Port Chester crowd and a go-to for out-of-town Manhattanites who love his Italian comfort food. Don’t miss the clam, chili, and oregano or pistachio and goat cheese pizzas. Waits can be long so if you’re trying to beat traffic just get take out from their curbside service.

An offshoot of the highly acclaimed restaurant Talulah’s Garden, this neighboring cafe and market offers a casual spot for eating in and gourmet foods and treats for taking out. Located directly on Washington Square park, the cafe serves wine and beer and premium La Colombe coffee. Talulah’s Daily is a comfortable place to enjoy healthy prepared foods and creative sandwiches, with many options for vegetarians. The gourmet shop offers a variety of unique non-perishable food treats that will survive your trip home.

Opened in 2012, the West Street Hotel wholeheartedly embraces its waterfront location. All 85 rooms have views of Frenchman Bay and are decorated in nautical Americana (think navy, red, and cream color schemes and lots of sailboat patterns on the upholstery). The hotel can arrange a lobstering trip on a real-deal commercial boat or an excursion to nearby Acadia National Park. There are more than 120 hiking trails that range from low-key to strenuous: Advanced climbers can summit Cadillac Mountain, the tallest peak on the U.S. Atlantic Coast. For a guided tour of the park with less effort, board Oli’s Trolley, which picks up riders across the street from the hotel.

This appeared in the June/July 2015 issue.

Looking for Las Vegas locals? Stop by Downtown Container Park, where boutiques sell their wares out of recycled shipping containers and locals sip wine while their kids run around the playground (also made from a recycled container). This hub in downtown Las Vegas features an ever-evolving rotation of shops and restaurants that highlight local artistic talent. Check programming for live (and often free) concerts, movies, and other events that take place on the stage toward the back of the park.

Touting itself as “killer burgers and manly drinks,” Urban Stack is an upscale bar food restaurant that just happens to be LEED certified. Choose from one of their signature burgers, with selections like standard beef burgers, alongside lamb, chicken, turkey and veggie patties. Urban Stack also prides themselves on their bar, which leans heavily on bourbon and, of course, “Tennessee whiskey.” Try the Dixie 8, made with Chattanooga Whiskey. The renovated Southern Railway Baggage Building is the best place to enjoy a cocktail in Chattanooga.

Beyond the crowds of central SoHo—in a formerly industrial nook with historic roots on the edge of the Hudson River—a neighborhood is emerging: Hudson Square. This is the home of Hotel Hugo, a stylish loft-inspired retreat with an Italian spirit that has brought a bit of European-inflected flair to the neighborhood. This extension of SoHo has long been known by New Yorkers for its nightclubs, restaurants frequented by locals, and of course, the gorgeous Hudson River Park, an uninterrupted promenade that stretches the length of Manhattan. Now it has a chic hotel, complete with a rooftop that has a Cuban cantina vibe that serves cocktails against a backdrop of the Hudson River.