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Even though you may have never been here before, Montréal’s Place St-Louis, in the Plateau neighborhood off of rue St-Denis, will probably look familiar thanks to the many tourism posters and guidebook covers that display its image. The graystone Victorian row houses, with details in pink, purple, and other eye-popping hues, embody a certain Montréal attitude—grounded in history yet with a playful, contemporary edge. The square was laid out in 1876 and has been described as one of Montréal’s most beautiful, with a European elegance thanks to its tree-lined paths and fountain. Students of poetry may want to pay homage to Émile Nelligan. A monument to the beloved Québecois writer sits in the southeast corner of the square near the house on avenue Laval where he once lived.

The Castelo de São Jorge, is one of the Alfama neighborhood’s most historically significant monuments. Plan a visit late in the afternoon so that you can explore every nook and cranny and learn about the castle’s abundant history. Stay for golden hour so that you can capture the light as it dances on the castle walls, and later to watch the sunset dip below the horizon.

Reserve an outside table at this popular enoteca, located on a quiet piazza around the corner from the crowded Ponte Vecchio. You can order a predinner snack or, better still, cobble together a full meal from the selection of crostini with delicious toppings like truffle sausage and melted cheese or spicy ‘nduja sausage. Other menu highlights include the antipasti platters of cheese and mixed cured meats. The staff can help you choose from the wine list, which focuses on small producers. (If you want to expand your wine expertise, guided tastings are also available here.)

Local markets remain a staple of Mexican life, and are typically a one-stop shop for a variety of needs. Manzanillo’s municipal market is no different, offering basic home goods, food staples and several on-site services, such as tailoring and minor repairs. Even if you don’t intend to buy, it’s worth it to take time to browse.

Once the source of two-thirds of the world’s emerald supply, Colombia’s gem-mining industry remains active, and visitors to the country count jewelry among their most coveted souvenirs. While there are many shops where emeralds and Colombia’s famed gold filigree can be purchased, Lucy Jewelry is considered one of the most professional: They’ve been in business for more than three decades.

Plaza Cívica, or Civic Plaza, is Ensenada’s central square, buzzing with locals and visitors. Busts of some of Mexico‘s most important historical figures populate the plaza, along with vendors selling everything from used books to jewelry, crafts and street-food snacks. A gigantic flag and, often, musicians make this a uniquely Mexican spot, perfect not only for shopping but also for photos.

If this building seems to radiate a celestial calm, that’s likely because it continues to serve as a working monastery. Founded in the early 17th century by the Augustinian order, the structure itself has undergone extensive renovations over the years, but its most distinguishing feature has never changed: its perch above the city. As the highest point in Cartagena, it rewards visitors with a panoramic view of all below. Gardens, a small museum and a shop round out the offerings here.

True, it would be impossible to pack that incredible vanity in your luggage, but that shouldn’t stop you from visiting Década if you love vintage furniture. After all, the staff can pack any object for shipping, and there are plenty of smaller items that will fit in your suitcase, no problem. This shop specializes in mid-century pieces. Plan ahead: it’s appointment-only.

Taking a turn around the town center is a long-standing tradition in most of Mexico‘s pueblos and even its biggest cities. It’s in these centers where you’ll find small and charming shops, cafés and restaurants, live music and public art installations. Manzanillo’s center is tiny and not as traditional as many others in Mexico, but still offers the opportunity to get a glimpse of daily life.

True, it’s not much to look at, inside or out, but this humble shop produces the best handmade sandals in all of Puerto Vallarta. Samples of the various styles of leather sandals, or huaraches, hang on white pegboard; choose one you like and try it on for size. If it doesn’t fit, don’t worry; the resident zapatero can make a pair custom fitted to your feet.

The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife’s favorite quote, and a local sight in Chicago. Sometimes people feel they must jet off to some far off exotic place in order to ‘travel.’ However, if you gaze anew at your immediate surroundings with fresh eyes, you will discover an entire host of wonderful surprises. Here we have Cloud Gate, located down in Millennium Park, back before they buffed out the seams. The contrast between the organic form of ‘the bean’ and the structured grid lines, along with the warped fun house mirror quality of the city, makes this a truly unique destination.

By far Nagasaki’s largest shopping area, this bustling strip, situated close to the Kanko Dori train station, brims with over 700 shops that range from tiny boutiques to sprawling department stores and high-end emporiums. If you can’t find what you want here, try the surrounding streets, which offer even more choices. The fact that Hamanomachi is a covered arcade means it’s perfect for rainy-day retail therapy, and there are also several key shrines and temples nearby if you need a culture break.

If you’re looking for a way to while away a rainy afternoon, head over to Mapo-gu and pop into the quaint boutique Object. This whimsical store is a shopper’s delight, and offers a wide array of stationery and jewelry designed by local artists, plus dishes, hats, bags, and even teddy bears and typewriters. Since the shop works on a consignment basis, the product selection is ever-changing, making it entirely worthwhile and necessary to return frequently, preferably with healthy wad of won in your wallet. 400-1 Seogyo-dong, Mapo-gu

After the evening call to prayer, several cafe trucks open up to people strolling along the stretch of Marina Island—across the water and parallel to the Abu Dhabi cityscape on the Corniche. From Arab coffee to karak (similar to chai tea), the drinks are the perfect way to end a day. On this particular evening, I enjoyed a piping hot Karak Zafron with a hint of saffron from the Street Bites Truck. With a park, a long jetty to a theatre, new restaurants, and some green park spaces, it is a local’s hot spot; yet the area remains mostly undiscovered by tourists and expats. The spit of land is perfect for long walks with a hot beverage from one of the trucks in the wintertime.

The cobalt-blue-and-brick-red residence where now-legendary Mexican visual artist Frida Kahlo grew up—and at times lived with husband Diego Rivera—is one of the city’s most consistently packed attractions; buying tickets in advance is strongly recommended. That said, the visit is essentially (and justifiably) mandatory and offers fascinating glimpses into this extraordinary woman’s life and work. In addition to holding some of her paintings, the house also functions as a showcase for her library, astounding wardrobe, and collection of pre-Columbian artifacts; it additionally bears witness to her close association with left-wing politics. What’s more, the museum portrays the artist’s struggles with depression, marital infidelities, disability, and illness. The house’s garden—home to a modest café and mostly bashful felines—makes for a great breather before more strolling in the Coyoacán neighborhood.