1. Perugia: the capital of Umbria is host to the cathedral San Lorenzo, the Oratoria di San Bernardino and the Galleria Nazionale dell'Umbria. Other sights of interest are the Fontana Maggiore and the Palazzo dei Priori, built on the Piazza IV Novembre. Going further back in time, the Etruscan well is a prime example of hydraulic engineering and the Volumni Hypogeum a wonderfully preserved funerary monument of the same era. Perugia has a university, a jazz festival and some of the world's most famous chocolates, the Baci Perugina!
2. Orvieto: the town is spectacularly set on a huge piece of volcanic rock with plunging vertical cliffs. Despite its many buildings of Romanesque, Gothic and Renaissance inspirations, Orvieto is mostly famous for its white and black marble cathedral. The frescoes depicting the Apocalypse are said to have inspired Michelangelo. The old city well, dug in rock, is 61 meter deep and numerous man-made caves carved below the town can be visited.
3. Spoleto: the town possesses a Roman theatre and amphitheatre, as well as a restored Roman house with mosaic floors. Its Festival dei Due Mondi is a lively three weeks of music, theatre and dance in the summer. A visit to La Rocca d'Albornoz, an impressive fortress where Lucrezia Borgia once lived, is recommended. On your way back, you will cross the Ponte delle Torri bridge and end your excursion with a lovely stroll in the woods.
4. Gubbio: Italians will tell you this city is Umbria's answer to Tuscany's Siena. A very old town dating back to the pre-Roman era, its Piazza Grande is one of the most beautiful squares in Italy. Located on a low slope of Mount Ingino, Gubbio and its rich history are worth a visit. It is the home of bronze tablets written in the extinct ancient Umbrian language by a priest of Jupiter.
5. Assisi: the birthplace of St. Francis is often described as the city of peace. The Giotto frescoes of the Basilica di San Francesco, his impressive burial place, are a must see. The Piazza del Comune was once a Roman forum, which has been partially excavated.