Otranto

In one of the first great Gothic novels, Horace Walpole's 1764 The Castle of Otranto, the English writer immortalized this city and its mysterious medieval fortress, and indeed Otranto (stress the first syllable) has had more than its share of dark thrills. As the easternmost point in Italy—and therefore closest to the Balkan Peninsula—it’s often borne the brunt of foreign invasions, including the massacre of 800 citizens by the Moors in 1480 because they refused to give up their faith. From here, you can see across the sea to Albania on a clear day. If you are a fan of the Neolithic, you will be interested in the Grotta dei Cervi, a few miles down the coast. The walls of the cave are covered with hundreds of prehistoric images, painted with red ocher and black bat guano.