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Like most Italian cities, Milan has an amazing and very visible history that spans two millennia of art and architecture. But what really distinguishes it from other città is the ever-present testament to modernism and modern architecture—all accessible via the charming vintage trams.

This glamorous villa is situated on Capri’s main road—and just a five-minute walk to the port—but JK Place feels like a refuge from the tourist throngs. Interiors have a chic, polished aesthetic that’s the embodiment of la dolce vita: The crisp white-and-navy spaces are filled with beautiful art and antiques, dramatic fireplaces, and colorful bouquets of blooms, while large windows and panoramic terraces capture views of rugged green hills that fall into the sea. (Yes, that’s Mount Vesuvius looming in the distance.) Posh touches continue in the guest rooms—think monogrammed pillows, canopy beds, wingback chairs, and marble- and mosaic-tiled bathrooms. Lemon trees scent the air throughout the property, from the elegant pool deck and on-site spa to the terrace bar, where sunset aperitivos are accompanied by tasty bites such as sea bream sliders and quail-egg canapés.

The summit of Monte Solarno, the highest point in Capri is almost 2,000 feet high! You can choose to climb it or opt for the considerably easier chairlift. Along the ride and at the top, you will enjoy an incredible 360-degree view over the island and sea. There is a small café for a cold drink. Make the short hike down to the sweet, tiny 15th-century Hermitage of Cetrella, a chapel where local sailors used to visit and pray for protection before setting out to sea.

Italians have a wonderful tradition of winding down the day and gearing up for the night—the early-evening aperitivo. Here are places to enjoy a glass of sparkling prosecco with a plate of savory snacks.

Since first reading about Capri as a teenager, I had dreamed about a shop like this. Crammed with hundreds of colorful tunics and beach coverups, Antica Sartoria makes it easy to leave with a bag stuffed full of gifts for oneself and friends back home. The inexpensive resort wear makes liberal use of polka-dots, paisleys, and ornate designs. Not a shop for wallflowers. There’s another outlet in Positano.

With divine pasta and funny putti, the handsome Duomo and the dreamy young Lotharios leaning on Vespas, with leather workshops and nonnas doing the weekly shopping, Florence offers visitors an urban experience that is equally rich in historic romance and everyday modern life. Join the parade of visitors to worship in the galleries of the Uffizi or watch the parade from a café table beside a busy piazza, but head to this Renaissance stronghold and make your own history.

Take two days to explore this coastal town, then venture to other villages along the Italian shores. Be sure to hike from Santa Margherita to Camogli along the edge of the Portofino promontory.

Passionate Mexico City foodies are rediscovering and reviving Mexico’s rural culinary delights.

Where to eat the best tapas in Madrid, Sevilla, Barcelona, and San Sebastián—plus how to order them like the locals do.

A journey through one of the world’s last, best travel secrets.

Monaco has more to offer than casinos, yachts, and fancy race cars. The Monte Carlo Beach Hotel reminds guests of the city’s glitterati glory days. The casino may steal the spotlight at Le Fairmont Monte-Carlo, but the Nobu restaurant and stellar spa deserve equal attention. Grand Prix fans will want to book a room at Port Palace for its terrific race views, not to mention harbor location. Housed in a 1900s Italianate-style palace, Hotel Métropole Monte-Carlo delivers over the top glamour.

São Paulo is one of the world’s largest cities and the largest city in South America. It’s also home to huge Japanese and Italian populations (a result of immigration in the early 20th century as São Paulo was an important part of the coffee industry). The city is known for its variety of food, nightlife, and culture, including art and museums. It’s also a great place to experience Brazil’s indoor and outdoor markets and see some very cool architecture thanks to Oscar Niemeyer’s work here.

There’s no shortage of diverse dining options in Zurich West - from the stylish tapas-sized dishes in Josef to the classical French-Italian cuisine of LaSalle. The opening of Zurich’s first permanent closed market created a plethora of restaurants including the modern Restaurant Viadukt and the popular Markthalle, offering hearty meat-centric dishes. Diners wanting to hit new heights should eat at Clouds - a high-end restaurant atop Switzerland’s tallest tower.

While most people think of Italy as a summertime destination, there are wonders to be found in this northern port city any time of year—especially winter! With hardly any tourists in these cooler (and slightly wetter) months, the city is quiet and calm and opens its doors to some incredible art exhibits, live operas, and wintertime flavors.

Italy’s fashion capital is of course full of stylish hotels. Luxury brand behemoths such as Armani and Bulgari both opened hotels in the city designed to embody their beloved aesthetics. A former fashion editor masterminded the three chic apartments at the intimate 3 Rooms Corso Como hotel. Park Hyatt Milan has a dreamy setting in an 18th-century palazzo, while the Seven Stars Galleria boasts a unique location in the oldest shopping mall in the world.