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This unassuming two-story plaza has become a popular Friday- and Saturday-night hangout for 20- and 30-something locals. In addition to its shops, Plaza Paseo Cobá is home to several restaurants and bars with a trendy, bohemian vibe that’s far removed from the beach area’s bump and grind. Feast on artisanal Italian at indoor-outdoor Casa Sofia, or dance to live music at the Public Place.

It is a fairly recent place, opened in February 2013, located close to Ribeira, in Largo São Domingos. This restaurant aims to bring to Porto a little bit of each region of Portugal. Focusing on small scale producers and in working directly with them, Joana and Sofia (the owners) managed to have a wide selection of traditional food items from all over the country. There are three things here that makes you have to go there: wine, muxama and cheese. “Muxama” is smoked tuna fish, coming from Algarve, and it’s quite hard to find it in Porto. Have it with scrambled eggs and tomato jam. Their selection of cheeses covers the entire country, including the Azores and its São Jorge spicy cheese. One of the most incredible chesses for me is “Caganita”. A buttery and flavorful cheese from Alcains, that here is served hot with olive oil and herbs…

Once Istanbul’s notorious prison, a lavish conversion in 1996 transformed this site, set amid the squiggle of lanes behind the colossal competing domes of the Hagia Sophia and Blue Mosque, into the city’s landmark Four Seasons Sultanahmet. Built in 1918, the hotel’s ornate neoclassical architecture has been finely restored, while the enclosed exercise yard is now a courtyard garden where guests can escape the hustle of the historic quarter. Classically designed rooms are awash with light blue and green hues and subtly scattered Turkish textiles and motifs.

On a hot summer’s day, cool off with cocktails overlooking the old city’s minarets on the rooftop A’Ya Lounge. Eagle-eyed history fans can hunt for the 1938 graffiti left by a former inmate on a pillar near the courtyard. Being neighbors with the Hagia Sophia has extra benefits. The Four Seasons’ Extraordinary Experiences service offers a privileged chance to explore Emperor Justinian’s greatest achievement without the crowds, on an after-dark tour of the Hagia Sophia.

On the rooftop of the Athens’ slablike Hilton Hotel, the Galaxy Restaurant & Bar serves elegant cocktails and delectable Mediterranean cuisine—but here the nearly cinematic view of the Greek capital steals the show. Come at dusk and take a seat on the terrace to watch the sky gently blanket the ancient city in blue, then darken and sparkle. Glamorous and alluring, this venue usually attracts an international crowd.

In Istanbul, the most authentic place to smoke nargile (also known as hookah and shisha) is Corlulu Ali Pasa Medresesi. The 300-year-old Medrese evolved from a religious school and dervish lodge during the Ottoman times to bazaar stores in the mid-20th century to its current form—a respite for locals and tourists from the bustling Grand Bazaar district. Relax amid the bubbling sounds of the nargile while indulging in the wafting aromas of fruity tobacco. Alcohol is not served; instead, savor a Turkish tea in a tulip-shaped glass or try “boomba” tea with lemon, hibiscus, and mint at the café on the left as you enter the complex. In winter, the warm milky cinnamon drink called salep is a local favorite. The customers are mainly men, but ladies, don’t feel intimidated. It’s a great place to people watch and meet locals who speak many languages. Corlulu Ali Pasa Medresesi is open till 2am and located on the tram line between Cemberlitas and Beyazit/Grand Bazaar stations. If you want my recommendation, try the apple and mint or rose and mint nargile—best shared with old and new friends. Afiyet Olsun (bon appetit)!

Adorned with more than 20,000 blue handcrafted İznik tiles, stained-glass windows, and the golden brushstrokes of a 17th-century calligrapher, the Blue Mosque is the legacy of Sultan Ahmet I (1590–1617). The young sultan audaciously wished to outdo the builders of Hagia Sophia, commissioning six minarets to match the number at Mecca’s Sacred Mosque (which now has seven minarets as a result). Today, this magnificent mosque is a place of worship for thousands who visit from around the world.

See thought-provoking contemporary art, world-class performances, and more at Toronto’s most treasured cultural institutions on this three-day itinerary.