Destination: Milan

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Compared with knockout Italian cities like Florence and Venice , Milan—considered the “handsome” sister—is gray and polluted and chock-full of Fascist architecture. But, as happens with siblings, the one without the looks usually has the most personality and style. Just as a perfectly tailored designer dress can change the woman who wears it, Milan’s star couturiers and luxury boutiques have transformed the city into Italy’s most chic, modern metropolis, one brimming with attitude.

That’s not to say Milan is only about designer shops and galleries. It is Italy, after all, where even the most industrial cities boast beautiful Romanesque churches and master artworks. Milan is home to the Duomo, one of the world’s most beautiful and largest cathedrals; an internationally revered opera house, La Scala; and, of course, Leonardo da Vinci’s The Last Supper.

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