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AFAR chose a destination at random—by literally spinning a globe—and sent comedian Jorma Taccone on a spontaneous journey to Nairobi, Kenya.

There was some trepidation among locals when Rosewood first announced its plans for this 13 plus–acre resort—the largest in the UNESCO World Heritage Site’s cobblestone historic center. But it didn’t take long for both residents and repeat guests to embrace it. The property evokes an authentic sense of place, with buildings made with the limestone used to build parts of the old town, decor crafted by local artists and artisans, and the same beloved ladies making fresh tortillas and sopes at breakfast since the hotel was under construction. Designed to feel like a hacienda, the 67 rooms and seven multibedroom townhouse residences—some of which are available to rent—are scattered around intimate courtyards and gardens, many featuring art and sculptures; a large outdoor pool, rotating indoor art gallery, and spa featuring treatments inspired by indigenous healing traditions are also on-site, while programs such as the Art Concierge help engage guests with the destination. The cuisine is also a big draw: Savor reimagined Mexican flavors and learn about regional wine at the gourmet restaurant; try a tequila tasting at the bar, which turns into a sushi-and-craft-beer spot on the weekends, or join locals for the popular Sunday brunch.

Rue Saint Paul is the oldest, the most popular, and the most iconic of Old Montreal streets. It was Montreal’s main thoroughfare in the 18th and 19th centuries, and although it doesn’t hold the same strategic importance today, it’s still at the core of Montreal’s destinations. Despite the tourist shops filled with souvenirs like moose-shaped shot glasses and maple-syrup everything, Saint-Paul Street still holds the grandeur it had back in the day, thanks to its stunning architecture. Ignore the shops and look up, admire the details of the windows and roof lines—to see what the street really is about. This street is ideal for a romantic, dimly lit, post-dinner stroll.

From traditional Moroccan dishes like pigeon pastilla to a chateaubriand steak accompanied by one of the area’s sturdy-yet-subtle red wines, dining in Marrakech means an intoxicating mélange of North African flavors and European-inspired cuisine. Whether you’re on a day tour of tastes around the Red City or you’re spending a weekend in town, you’ll eat in central courtyards, high-end hotels, on balconies, and, if it’s a burger you’re after, the converted schoolhouse of Cafe Clock. One of the flavor threads through all of it: Morocco’s mint tea.

Finding a charming alpine town snug at the base of Whistler and Blackcomb mountains may make skiers, hikers, and lovers of beauty feel like they’re having a fever dream, but the dream is real. Whether you come in winter for the world-class downhill skiing and snowboarding, or in summer for mountain biking, hiking, gallery-hopping, and long evenings spent on restaurant decks, you’ve found Whistler Village, one of the jewels of British Columbia.

Whether you’re searching for a spot to sip a craft beer while watching the Northern Lights or a popular bar that serves up au courant cocktails and electronic music, Iceland has you covered. Reykjavík is, easily, Iceland’s most popular city for those who like to pair drinking and dancing, but it also offers plenty of places to perch if you’re more in the mood for conversation with locals over a nightcap. One of the city’s coolest trends: many of the coffee shops turn into buzzing dance parties during the evening hours. Of course, many of Iceland’s most-celebrated restaurants also go to town when it comes to cocktails. Worry not, you’ll never go thirsty.

These gorgeous islands are surrounded by the turquoise waters--and pink flamingos--of your Instagram dreams. From scuba diving on Grand Turk to horseback riding on the white sand of Long Bay Beach, you’ll spend plenty of time enjoying life in and near the water. But you’ll also find a fascinating National Museum, shopping in and around the capital of Cockburn Town, the craftsmen of Conch Bar and, speaking of conch, a deep dive into farming that favorite local delicacy.

The Summer Restaurant in the Hotel Stary offers top quality food with a bird’s eye view over the market square (just be sure to ask for a table with an OId Town view).

For adventures in Old Strathcona, at the heart of Edmonton’s cultural, culinary, and nightlife scenes, book a night or three at the Euro-style Varscona Hotel on Whyte. Historic Old Strathcona is home to the iconic Stracona Railway Station (built in 1908), the Princess Theatre (the city’s oldest, built in 1915), and the Strathcona Hotel (built in 1891). The hotel has wonderfully appointed rooms, an excellent breakfast nook, a 24-hour business center, a fitness center, an “oak and leather” lobby with a chill vibe, and an attentive staff always at the ready with a recommendation for a cafe, coffee shop, or curio store. The hotel is within walking distance of Old Strathcona’s 100+ restaurants, cafes, bookshops, and music shops, and makes for a brilliant base for exploring Alberta‘s capital, especially when Edmonton is hosting one of its many festivals — one for nearly every day of the year, in fact, from the Edmonton International Fringe Festival (August 14-24) to Western Canada Fashion Week (September 18-25). [Flash traveled to Alberta courtesy of Travel Alberta.]

Galeria Delbarrio is an extraordinary place to see Peruvian pop art. The gallery mixes the old and new, modern and traditional, in a very fun way. They have paintings, comics and an extensive collection of rustic-pop furniture spread throughout a 1840’s house. Just the house itself would be worth the visit. It has the traditional architecture from the time Chorillos was a beach resort town where the rich families from Lima spent their summers. The restoration preserved the domes, glasswork and original ceilings, adding a splash of color that brought the place to life. After the visit, take a walk around the neighborhood and enjoy its tranquil old town atmosphere. Make sure you finish by the boardwalk, where you’ll be wowed by one of the best views of Lima.

Go Bar occupies an old colonial house on a leafy Mendoza street (formerly Winery & Company). Its old, worn wooden floors speckled with sunlight have just the right vintage feel for wine browsing. It’s several rooms are stacked with wrought iron shelves featuring the region’s numerous wine labels. The staff is friendly and knowledgeable and will give you the perfect packaging to carry wines in your suitcase back home. Chile 898 (corner of Montevideo)

The Tule tree is estimated to be over 2,000 years old. It’s not the oldest or the tallest, but at about 30 feet in diameter, it is the widest tree in the world, and it’s quite impressive. The species is Taxodium mucronatum, but it’s commonly known as a Montezuma Cypress. If you visit on the weekend, you can ask one of the local children who act as guides to give you a “tour” of the tree—they point out figures in the natural formations of the tree’s bark and branches.

There is something fundamentally different in the air of this Eastern Townships winery—something I couldn’t quite grasp but that made me want to stay forever. The winery, which specializes in ice wines and ciders, was founded a few years ago by three young, passionate investors and lifelong friends, and it has since received immense praise, both from its clientele and the wine industry. For me, I think the setting is what sets it apart from other wineries. A charming bright-red barn overlooks acres of dense forest and rolling hills.

Sultan Bazaar is a labyrinth of lanes in the old city offering commercial goods, clothes, jewelry, shoes, silverware, handicrafts, and produce. It is not generally frequented by many tourists and therefore makes for an engaging experience with the locals. Stop by Shanti Fashions for the latest styles of traditional Indian dresses, known as salwars. Also close to the bazaar is Maheshwari Parameshwari, one of the oldest theaters in Hyderabad.

This sprawling badi on the left side of the lake bears the distinct honor of being the only one in town with a sandy beach. Other draws include a 5-meter tall diving tower, barbecue areas, an expansive green lawn and phenomenal mountain views. While it’s a slight jaunt from the tourist attractions of the Old Town, it’s well situated for other pursuits; the Rietberg Museum and Belvoir Park are just a short stroll away.