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From magnificent hilltop towns to famous ancient cities, some of the world’s most beautiful destinations can be found in Italy. In fact, Rome is the third most-visited city in Europe, and three others were ranked among the 2017 Top 100 City Destinations survey by Euromonitor International: Milan, Venice and Florence. While each one is surely worth visiting, if you’re looking for the most beautiful cities to explore, you won’t want to miss these.

San Gimignano

This gorgeous hilltop town in Tuscany is famous for its medieval architecture – so much so that it’s been called Italy’s “Medieval Manhattan” with a skyline that includes 14 stone towers dramatically rising from the tranquil countryside. At the city’s peak there were over 70 towers, as tall as 160 feet, each constructed by its patriarch families in a competition as a display of wealth. While just a fraction of them can still be seen standing today, they offer spectacular views of San Gimignano and the lush surrounding valley.


Cortina may be a popular ski resort town, but it offers a whole lot more, including a 1,000-year-old history and breathtaking scenery, surrounded by the jagged peaks of the Dolomite Mountains in the southern part of the Alps. Referred to as the “Pearl” or the “Queen” of the Dolomites, jaw-dropping views await in every direction. With an enticing town center filled with historic buildings coupled by the miles and miles of trails nearby for taking in stunning mountain vistas, you may want to book a walking tour in Italy.


The “White City” as Ostuni is often called, is another hilltop town, but this one is just a few miles from the glistening sapphire expanse of the Adriatic Sea. Get lost within its maze of enticing alleyways and narrow streets, arches and staircases that sparkle under the ever-present rays of the sun, brightened even more by colorful green and blue doors. You’ll find a Gothic-style cathedral at the highest point in the city, a rare treasure here in a place where most churches were built in ornate Baroque or austere Romanesque styles. There are also plenty of small, independent boutiques selling a variety of goods from fashions to handcrafted items and souvenirs, as well as gourmet food shops with inexpensive local olive oils and wine and an endless array of outstanding restaurants.


The Southern Italian town of Matera is a UNESCO World Heritage Site notable for its unique homes and structures that were carved out of limestone rock along the cliffs of the Basilicata region. The oldest continuously inhabited settlement in history outside of Petra, Jordan, the stone dwellings date all the way back to 15,000 BC. It was first occupied in the Paleolithic Age, with the natural caves eventually expanded into living spaces by artisans and peasants throughout the classical and medieval periods. Today, the same underground residences have been transformed into stylish eateries and cave hotels that make for an especially exotic experience.