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Partly owned by part-time Charleston resident Bill Murray, Harold’s Cabin is a nutty combination of Murray’s sweetest comedic roles and Wes Anderson’s cockeyed art direction. This former neighborhood corner grocery store (opened by the namesake Harold Jacobs in 1929) keeps up the bodega tradition by offering some local goods on shelves and in refrigerated cases in the front, like pizza dough and milk, as well as fancier artisanal stuff. The rest of the place is more Wes Anderson—plaid-upholstered furniture, stenciled murals, vintage porch gliders, knotty pine panelling—the look is definitely not haphazard, though, it’s more balanced and a deliberate design. Entrust your cocktail or beer wishes to the affable veteran bartender, Drew Childers, who will draw from the extensive variety of local brews on tap or mix you a cocktail that draws inspiration not just from the bottles behind the bar but from the vegetables grown in the extensive roof garden as well. In addition to dinner entrees like a bison burger and a popular three-cheese ravioli in mushroom sauce, a ‘Graze ‘n Nosh’ menu section includes boards: a snack board is served with a sleeve of Ritz crackers teetering on a plank beside with cheese curds, slices of pepperoni, ham salad, pickles, and savoure cheeese; another board has a generous serving of cured salmon, latkes, pickles, and beet horseradish. The crowd is full of locals (the mournful face of a dog tied up outside implies that her evening constitutional was waylaid) and much of the conversation at the bar concerns surf reports and the merits of the beers on tap. There is frequently live music, as well as goofy regular events like a monthly Johnny Cash day on which customers dressed in black get a discount. Head out to Hampton Park Terrace and join Harold’s Cabin’s low-keyed party.

A pioneer of the Hawaii Regional Cuisine movement, chef Mark Ellman showcases his thoughtful approach to cooking at Mala Ocean Tavern, a harbor-front eatery with dramatic sunset views. Come here for well-executed fusion fare like ahi bruschetta, whole wok-fried Hawaiian fish, and a vegan mushroom Bolognese pasta with local shiitakes, as well as signature cocktails like the Spa Day (cucumber, vodka, fresh watermelon juice) and the LBC (gin, passion fruit, basil simple syrup, fresh lime, and soda). Party animals will be happy to learn that the restaurant also offers a late happy hour each evening from 10 p.m. to midnight, plus live music and DJs spinning vinyl on Friday nights.

The Natural History Museum houses some 35 million specimens and artifacts spanning 4.5 billion years in history. But it isn’t just what’s inside this structure that’s historic: The main building itself dates all the way back to 1913, when a Sunday school teacher—upset by the seemingly unstoppable influx of saloons, gambling locales, and other centers of vice—convinced the city to develop what’s now called Exposition Park. Fast-forward to the present, and the Natural History Museum is more than just a place to see weird animal bones and models of long-extinct Homo sapiens. The museum hosts plenty of public events throughout the year, including mini nature festivals, evening cocktail parties, and opportunities for community science. The neighboring California Science Center is a draw for the kiddos, and Exposition Park as a whole is occasionally leased out for large-scale music fests.

High above Vail Valley, atop Beaver Creek Mountain, is the oasis that is the Ritz-Carlton, Bachelor Gulch. You can’t beat the hotel’s ski-in, ski-out access, but a major makeover at the end of 2013 means the hotel offers even more perks. The new look (think rustic lodgepole pine beams and huge stone fireplaces) was inspired by the great lodges found throughout America’s national parks. The work of Colorado artists can be found throughout the hotel. In addition to a new restaurant called Buffalos, there’s the new Bachelors Lounge that caters to wine and spirits lovers and cigar connoisseurs. Stylish guests with an expense account can outfit themselves in fancy new gear sold at the outpost of the alpine shop Gorsuch. My favorite perk is returning to the hotel at day’s end and being greeted with a hot cup of cocoa.

Belly up to this Wailea bar, which dazzles with a display of blue-glass Japanese fishing floats, for Hawaii’s best mai tai. Here, chef Peter Merriman, a pioneer of Hawaii Regional Cuisine, brings his genius to the classic cocktail, adding a thick head of honey-lilikoi (passion fruit) foam. Be sure to also score a table for later, as Monkeypod Kitchen does double duty as one of Maui’s top restaurants. Menu standouts include such seasonal dishes as kiawe-roasted squash ravioli, coconut-corn chowder, Hamakua wild mushroom pizza drizzled with truffle oil, and bulgogi pork tacos with Asian pear and house-made kimchi.

Nick’s is a Southern California institution, with coastal locations in Long Beach, San Clemente, Manhattan Beach, and Pasadena. The Laguna outpost has the others beat, however, thanks to its perch just across the street from Main Beach. Diners can head here after a long day in the sun for delicious takes on classic American dishes, from buttermilk fried chicken and San Francisco cioppino to rib eye melts and cheeseburgers with Thousand Island dressing. Whatever you choose, pair it with a house cocktail (you can’t go wrong with the jalapeño-watermelon margarita) as you watch the sun set over the Pacific.

The Glenn Miller Orchestra introduced America to the Chattanooga Choo Choo and Track 29 in the 1940s, but the train and its home at Terminal Station date all the way back to 1909. In 1973, the original Pullman train cars were converted into luxury hotel rooms, transporting guests to a past era of travel—albeit with modern amenities like high-speed internet, refrigerators, and coffeemakers. Spend the night at the hotel, or simply explore the former terminal complex, which now features multiple restaurants, bars, retail outlets, a comedy club, and a beautiful rose garden. At Gate 11 Distillery, you can even sample artisanal spirits straight up or in carefully crafted cocktails.

Downtown Orlando is a very social place, with blocks of bars and restaurants that stay busy from happy hour through late night. Along Orange Avenue—but delightfully removed from the more boisterous downtown stretch—this rooftop lounge overlooking Ivanhoe Row is a local favorite for drinking craft cocktails al fresco. Ride the glass elevator up the third-floor deck, where a horseshoe-shaped bar is shaded from the sun but open to the breezes. Seasonal sangrias spiked with whatever fruit is at peak ripeness go down easily. And another house favorite is the Majors Mule, which puts a tequila twist on the ginger beer and fresh lime classic.

The narrow Boca Paila highway runs down the edge of the Riviera Maya in Tulum, dividing the jungle from the sea. Tucked away at kilometer-marker 7.5 lies Casa Jaguar, a haven for the best of both worlds. The restaurant emphasizes Caribbean flavors, using fresh, local ingredients and prepared food and drink with Mexican flair. Try the grilled aguachile seafood cocktail, or the sea bass with corn masa, and wash it all down with a drink of copal mescal, the perfect foil for intense local heat. Beyond being a great restaurant, Casa Jaguar is famous for its “Dinner and Party” concept: there’s a jungle-focused celebration every Thursday with artists and alternative live music.

With its white, single-story exterior and dark window frames, this 12-room inn on the Saratoga Race Course looks like a Tudor take on a vintage motor hotel. Once inside, however, visitors realize the boutique property is much more luxurious than a roadside motel. Rooms feature light-wood bed frames and equine-inspired art, while the bar offers an excellent wine and cocktail menu, which regular happy hours featuring Moscow mules served in copper mugs. There’s also an outdoor patio, where the hotel can arrange barbecue meals on request, and free bike rentals for those who wish to venture farther into town.

This lovely contemporary-American eatery anchors the Ballard Public lofts. Chef Shaun McCrain shows off his time spent in the kitchen at New York City’s Per Se with reimagined classics like foie gras layered into a terrine with apple, black sesame, and a gelée of dashi (a Japanese broth). Even the cocktails are innovative—ask for the restaurant’s fresh take on a Pimm’s No. 1 cup. Reserve ahead for a leisurely dinner, or just belly up to the bar. And if you don’t have time for that nonsense, no worries! You can order a takeaway case with goodies like truffled deviled eggs, white bean spread, and lemon-thyme flatbread.

Chef Julia Sullivan grew up in Music City before moving away to study at the Culinary Institute of America and work at restaurants like New York’s Per Se and Blue Hill at Stone Barns. When she returned home, she opened Henrietta Red with sommelier Allie Poindexter in the culinary hotbed of Germantown. The women bring a strong oyster game to landlocked Tennessee as well as options like wood-roasted pork sausage with broccoli rabe and rhubarb mostarda. Diners can take a seat at the long marble bar for natural wines and craft cocktails or settle into the dining room, where white walls and wood tables create a bright, homey feel.

Rooftop bars are a dime a dozen in New York and many of them offer great views of the city’s skyscrapers. For now, at least, none is taller than Bar 54, which sits atop the Hyatt Times Square on the 54th floor. There are aspects of the decor that scream “chain hotel bar” but who’s paying attention? The view is what it’s all about here, especially at sunset. And the drinks, developed by Julie Reiner, owner of the popular Brooklyn cocktail lounge, Clover Club, are attention grabbing, too. Try the Cucumber Jewel, with gin, Lillet Blanc, Cappeletti, pampelmousse, lemon, and cucumber.

This family-run hotel, originally opened in 1886, is steeped in history from its classic furnishings to its esteemed guests. Literary legends William Faulkner and Ernest Hemingway have stayed here; Tennessee Williams wrote about the hotel in his play The Rose Tattoo, and Truman Capote was known to prop up the Carousel Bar & Lounge on many a night. The merry-go-round–like bar (which makes a complete revolution every 15 minutes) is probably the hotel’s most famous feature, and a Vieux Carre cocktail there is de rigueur. Guests will also want to visit on-site restaurant Criollo, which offers an updated take on traditional N’awlins fare.

As the number of bars in Krakow has gradually increased, the spots from which to enjoy a sunset drink have also expanded. One of the most glamorous spots is the Sky Bar on the roof of the Hotel Stary, overlooking the main square. Order a cocktail or a decadent homemade dessert and watch as the bustle of the city plays out below to the occasional tune of the unfinished bugler.