Perched on a hillside in northern Umbria 105 mi/170 km southeast of Florence, charming Gubbio, Italy, has changed little since the Middle Ages.

Its steep cobblestoned streets, portals, fountains and beautiful views of the countryside below are beguiling.

Be sure to visit the Piazza della Signoria and the 14th-century Palazzo dei Consoli. Take the funivio (a ski-lift-type contraption) up to the Basilica di Sant'Ubaldo for a thrilling ride up an impossibly steep hillside with breathtaking views from the top.

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