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Willis Tower—originally known as the Sears Tower—was the world’s tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its “bundled tube” design by architectural firm Skidmore, Owings & Merrill was originally inspired by a handful of cigarettes and the innovative bundling changed the construction of supertall, wind-resistant buildings thereafter. The tower’s height is even more thrilling when measured from the 103rd-floor windows of the Skydeck observatory and the Ledge, a glass-enclosed box which juts more than four feet out from the side of the building so that visitors can (gingerly) walk out and stand 1,353 feet above the street.

Mile-long Newbury Street, lined with handsome 19th-century brownstone homes, is synonymous with shopping in Boston; it’s also the place to go to get your hair done up nice. Between Arlington Street and Massachusetts Avenue you’ll find an eclectic mix of boutique and designer shops, hair salons, art galleries, and restaurants that generally skews upscale (Tiffany’s, Chanel, Dolce & Gabbana) but also includes the original location of the Newbury Comics record store and a T.J. Maxx. Eminently strollable and dotted with sidewalk cafés, Newbury Street is the hip heart of the Back Bay neighborhood, perfectly distilled at eye-candy drinks-and-dining hot spots like Sonsie and Stephanie’s on Newbury.

Long considered one of the top hotels on Oahu, the Kahala has always been a particular favorite among the type of guests who travel with their own security detail. A number of past U.S. presidents, plus kings, queens, princesses Grace and Di, a handful of Nobel Peace Prize winners, rock stars, and movie stars, all have slept under its venerable roof at some point during the hotel’s 50-year history. The see-and-be-seen set moved on long ago, but privacy seekers still make a beeline here. They’re drawn less by the property’s fabulous beach (though that’s reason enough to stay here) than by its exclusive location—in a well-fortified cul-de-sac in the ritzy Kahala neighborhood. But there’s a warm and fuzzy side to the hotel, too. A pod of dolphins has full-time residency in the hotel lagoon, and visitors of all ages can swim with them (for a fairly steep fee). Rooms have a preppy beach house vibe—raffia ceiling fans, linen loveseats—and many come with heart-stopping sea views.

This might be the most photographed store in Florence—the charming but cluttered scene includes strings of dried garlic and chilies, baskets of fresh fruit, colorful ceramics, wooden serving utensils, wild-boar salami, Tuscan olive oil, and handmade copper pots—with displays inside the shop and spilling out onto the sidewalk. This historic establishment, on the ground floor of the old tower of Borgo Santi Apostoli, is so friendly that the owner will pour you wine and offer a few bites of pecorino cheese while you decide how much room is left in your suitcase.

There is perhaps no landmark of San Francisco, and perhaps even the entire state of California, more iconic than the Golden Gate Bridge. This much-photographed bridge spans the Golden Gate, the strait separating San Francisco (to the south) and Marin County (to the north). The 2.7-kilometer-long (1.7-mile-long) bridge was completed in 1937 in one of the most remarkable engineering feats of its time. Although the idea of traversing the Golden Gate by way of a bridge had been discussed for decades, the fear that fog and wind would make the project nearly impossible discouraged planners. In the end, the bridge was completed in four years at the cost of $35 million as well as the lives of 10 construction workers. A pedestrian path along the bridge offers stunning views of the bay and San Francisco as well as an up-close look at this Art Deco wonder.

The most enviable address in Waikiki, the beachfront Halekulani is all about restrained elegance and pitch-perfect service. The hotel dates back a century, though it was entirely rebuilt in the 1980s—and the room decor—fifty shades of white and plantation shutters framing the turquoise sea—complements the scene outside. The beach itself is small and usually mobbed, but the pool is a dream—a giant oval big enough for laps, and quiet enough (few kids here) for a long doze under your chaise’s umbrella. The grassy courtyards and seaside restaurants are just as improbably serene; some might say stuffy, but for others, the reliably hushed atmosphere is a welcome tonic to the hubbub of Waikiki, just outside the Halekulani’s marbled entrance.

Tucked away in the heart of downtown Seoul is the quaint Insadong district, where a Korea of yore comes to life in the form of traditional artists and musicians, shops selling Korean crafts and souvenirs, and street performers dressed in native costumes. This is the place to go if you’re set on buying the wooden masks, paper lanterns, and tea sets that the country is famous for. Two other stores also stand out from the crowd in Insadong: Gounjae Handcraft can be smelled before you even enter the door. This handmade soap shop, in the small brick courtyard of Ssamji Gil Center, offers sumptuously scented soaps, lotions, and bath products in scents like avocado, ginger, and almond. I love the tiny, traditional mask-shaped soaps that make inexpensive and lightweight souvenirs. The Ee Gee boutique is a veritable treasure chest bursting with glimmering necklaces, bracelets, and other one-of-a-kind baubles–it’s located on Insadong’s main drag.

Within the 18th arrondissement in Paris France, high atop the city, resides the wonderfully beautiful, hilly neighborhood of Montmartre. This diverse and eclectic section of the city can be a bit busy with tourists, but the views of Paris and the splendor of the Basilica of the Sacré-Cœur are certainly worth it. Riding the funicular is rather novel, but not necessary if you’re willing to climb the 300+ steps to the summit. This is an area to be explored on foot, as is nearly all of Paris. The shops, theaters, and forever famous Moulin Rouge should not be missed. The streets are intimate, the shops unique, and the overall feel of this place speaks of a youthful, colorful Paris.

In the tiny, quirky town of Hilo, a perfect date night starts with a stroll on the elevated sidewalks along the Victorian-style storefronts to check out the local creative scene. It ends at Kaleo’s Restaurant, where flip-flops are welcome and smiles guaranteed in the finest restaurant in town. The farmhouse appearance of Kaleo’s is indicative of the warmth put into the menu—a locally inspired selection of flavors that includes such dishes as Dynamite, a seafood and mushroom dish with veggies baked in spicy mayo, or the hearty Kaluna steak and potatoes. Cap it all off with a Chocolate Lava Cake while you reminisce over your molten experiences at Volcanoes National Park. But before digging into dessert, enjoy the live music—it creates a lovely atmosphere to let the romance sizzle.

You’ll know Tipsy Tuna when you see it: the bright pink, purple, blue, and green tables and chairs, the leopard print on the walls, the snarky signs plastered everywhere—even on the ceiling. Only slightly less local than its equally loud neighbor Barefoot Bar, Tipsy Tuna is the place to be for happy hour. Most nights, you can find DJs spinning tunes for dancing or lively karaoke going on past 9 p.m. As the name suggests, most people come here for the drinks, which are numerous, cheap, and strong. The food, however, isn’t to be scoffed at, especially if you’re into well-utilized spices and a million types of salsa.

Read articles from this print issue of Afar Magazine.

Explore museum exhibitions, ride the light rail, and take a cocktail class in a three-day itinerary filled with this North Carolina city’s many delights

Tour the Greek Isles on Windstar’s seven-day cruise through the Aegean, which includes ancient sites, beautiful beaches, and one-of-a-kind experiences.

Explore Michelin-starred restaurants, local and seasonal delicacies, and more in Reykjavik, Stockholm, Gothenburg, and Copenhagen.

In this week’s episode of Travel Tales by AFAR, a bluegrass fiddler travels to Vienna to learn how to sing—and how to embrace the city’s most famous art: opera.