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Spoleto

A truly charming Umbrian hill town, Spoleto is best known for the Festival dei Due Mondi (Festival of Two Worlds), an annual festival of international music, theater and art held during the last two weeks of June and the first two weeks of July. Begun by Gian Carlo Menotti in 1958, it includes performances of opera, dance, theater, concert and film (tickets are best purchased six months to a year in advance). Spoleto is a beautiful Renaissance town in itself, with arched, narrow, winding streets and Roman architecture that includes a theater, an arch and a remarkable first century AD house that belonged to Emperor Vespasian’s mother. Roman stonework forms part of many buildings. Just on the other side of La Rocca, an old prison and hilltop fortress, is a spectacular gorge – cross the 750-ft-/233-m-long, 14th-century brick footbridge (built over an older Roman aqueduct) for a breathtaking view. 60 mi/95 km northeast of Rome.

San Gimignano

One of the most charming and picturesque of all the Tuscan hill towns (and that’s saying a lot), San Gimignano is noted mainly for its medieval towers. They dominate the town in the way that skyscrapers dominate modern cities. At one time there were more than 70 towers (built as symbols of wealth and as a security precaution by the town’s prosperous merchants), but only 14 remain today. Walk through the wonderfully preserved town square, the Piazza della Cisterna, and visit the 13th-century town hall, the Palazzo del Popolo. There are good views from the Rocca citadel, and the entire town is a great place to stroll and soak up the atmosphere. If you visit on the third weekend in June, you’ll be rewarded with the Ferie dell Messi, a medieval parade in full costume followed by jousting tournaments. It takes quite a bit of time to get to San Gimignano from either Rome or Florence, so we suggest that you spend at least one full day and night there. That way, you’ll also get to see the town after the day-tripping tourist hordes have left. Another option is to stay in nearby Volterra, with its Etruscan ruins and vertiginous views from high on a forbidding hilltop. 25 mi/40 km southwest of Florence.

Ravenna

Located on the Adriatic and equidistant from Venice and Florence, Ravenna is best known for the wonderful mosaic decorations of its churches and tombs, relics from its Byzantine past. In particular, the mosaics at the peaceful and lovely Tomb of Galla Placida (the sister of an emperor), the Church of San Vitale, the Baptistery (Battistero Neoniano) and the Basilica of Sant’Apollinaris are among the most interesting in all of Europe. They are famous for their striking and varied colors, as well as for their symbolic meanings (Dante mentioned them in his Divine Comedy). The city produces modern mosaic artists, too, at Ravenna’s School of Mosaicists. Be sure to see Dante’s tomb, located in the Church of San Francesco. The poet spent the last years of his life in Ravenna after being driven out of Florence. For years Florence tried to acquire his remains, but Ravenna steadfastly refused. The city honors him with a literary and theatrical festival in September. Ravenna is not to be missed – work it into any trip that includes nearby Bologna, Rimini, San Marino or Urbino. 115 mi/186 km south of Venice.

Pompeii

On the southern outskirts of Naples lies Mount Vesuvius, the volcano whose eruption in AD 79 covered Pompeii and Herculaneum (Ercolano) with tufa stone and volcanic mud. The cities remained covered until the 1700s, when a farmer discovered Pompeii while digging a well. The two cities (reached on the Circumvesuvio railway) give you a real grasp of what life was like in the Roman Empire – they are exceptionally well-preserved. Pompeii was a city of nearly 20,000, and in the summer it can be exhausting to see it all, so we recommend using an audio guide, an authorized guide (he or she should wear proper identification) or a good guidebook in order to focus on the highlights. Pompeii is 20 mi/30 km southeast of Naples.

Perugia

The capital of Umbria, Perugia is a beautiful hill town and important center for Umbrian and Tuscan art. Around the town’s main square, the Piazza Novembre IV, visit the National Gallery in the Palazzo dei Priori (it houses works by Fra Angelico, Piero della Francesca and Perugino), the Gothic cathedral and the 13th-century marble and bronze Maggiore Fountain. The chapel in Piazza San Severo has frescoes by Raphael and Perugino. The crumbling walls of Rocca Paolina, a fortress built in 1373, offer great views from the highest point in town. There’s a well-preserved Etruscan arch that was built right into the medieval wall fortifications on the northern side of town – look for the inscription, “Augusta Perusia,” that dates from the first century AD. The Carducci Gardens offer a beautiful view of the surrounding countryside. Allow at least half a day for the city itself. Perugia would also make an excellent base to explore the surrounding region by car. Assisi, Gubbio, Orvieto and Urbino are all close by.

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