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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.

The exterior of this Midtown lodging won’t win any design awards—the building previously housed an insurance company—but that’s what makes the art-filled, wood-accented lobby such a pleasant surprise upon arrival. With its plush leather sofas and moody interiors, the Hutton exudes down-home charm with a modern touch: A friendly sit-down check-in coupled with swift service at the lobby’s WestEnd Kitchen & Bar make the hotel a favorite of touring musicians and visiting celebrities. Oversize guest rooms (some of Nashville’s largest) feature soft blue and gray tones, fabric-covered walls, and vibrant artwork. At the 5,000-square-foot on-site music venue Analog, you can sip creative cocktails while listening to some of the city’s top performers, but if you’d like to see the view from the other side of the microphone, the hotel’s Writers Studios is stocked with state-of-the-art equipment for laying down your own tracks.

Leb-i derya is one of those fabulous fancy restaurants perched high above the streets of Beyoğlu with amazing views of the Bosporus, Maiden’s Tower, Asia and old Istanbul’s peninsula. You could walk past the building so many times on its dimly lit street without realizing how magnificent the view from the top is. This light and bright sophisticated rooftop restaurant offers traditional Turkish flavors with a modern twist, as well as gourmet-style international favorites. In summer, management opens the doors to an open-air terrace ideal for sunset cocktails. It really is an iconic city rooftop for special occasions—or for saying good-bye to Istanbul on your last night in the city. Enter off the sloping Kumbaracı Yokuşu (street) which runs off Istiklal street near Tünel. Reservations are advised.

One of the delights of Valparaíso is exploring the colorful hillsides that ramble down towards the sea. Take the century-old funicular elevators Ascensor Concepción (Turri) or El Peral near the main plaza, constructed between 1883 and 1911. Once high into the hills of Cerro Concepción & Alegre, explore the meandering alleyways and cobblestone streets on foot. There are boutiques, cafés, mom-and-pop shops, old school bakeries, bars, restaurants, art galleries, and church bells tolling. It often feels more like a small village than a city. Climb up and down the many staircases often lined with bright graffiti. In the distance, the bay gleams in sunlight and the busy port never tires. At dusk, the lights twinkle like fairylight. Grab a table at a spot like Café Turri for a view of the sunset and a cocktail.

There’s a reason chef Tony Maws has developed a cult following at Craigie on Main. For years, the cozy restaurant has been turning out beautiful food in a space that feels like it might be your friend’s dining room. Its commitment to regional, organic sourcing has been called a tad obsessive, but once you’ve eaten there, you’ll appreciate the attention to detail. The menu is created only after the best of the day’s ingredients have arrived; the wine, beer, and cocktail list also features the same local flavor. If you want the full experience, the chef’s seasonal tasting menu is a must. The corned-beef hash on the brunch menu is one of the reasons the restaurant regularly ends up on “Best of Boston” lists. (House-made doughnuts in a pool of golden caramel sauce don’t hurt either!)

A new addition to the Jo’burg night market scene is the House & Leisure Night Market at Katy’s Palace Bar, which is also home to an antique store located on the ground floor and The night market featured a good variety of local arts and crafts as well as some locally produced foods and drinks. On the night there was a competition to win a prize hamper consisting of awesome prizes from all the vendors at the market, and amazingly my friend and I ended up winning! Katy’s Palace Bar is normally a private venue for hire, however they are also open for selected public events and every first Sunday of the month for easy lunches and cocktails on their balcony which looks out over the city of Sandton