There's something otherworldly about this jewel of a medieval town tucked away in a mountainous corner of Umbria. Even at the height of summer, the cool serenity and quiet of Gubbio's streets remain intact. The town is perched on the slopes of Monte Ingino, meaning the streets are dramatically steep. Gubbio's relatively isolated position has kept it free of hordes of high-season visitors, and most of the year the city lives up to its Italian nickname, La Città del Silenzio (City of Silence). Parking in the central Piazza dei Quaranta Martiri—named for 40 hostages murdered by the Nazis in 1944—is easy and secure, and it's wise to leave your car in the piazza and explore the narrow streets on foot.
At Christmas, kitsch is king. From December 7 to January 10, colored lights are strung down the mountainside in a shape resembling an evergreen, the world's largest Christmas tree.