One of my favorite Umbrian towns is Gubbio.
This ancient city predates the Romans by 2 to 3 centuries and features amazing Roman influences including its Roman Theater. Still in use today, this amazing “ruin” sits just outside the walled city and is used for the annual Festa dei Ceri each May. But even more beautiful is the city inside the medieval walls, which is so extraordinarily intact.
The museums, cathedral, shops, and piazzas are unspoiled Italy at its best. And in addition to its architectural charm, Gubbio is a center for maiolica, the beautiful ceramics known for their deep colors, historical and legendary themes, and geometric and floral designs. In many of the ceramic shops, you can watch current generations of ceramic painters continuing these traditions.
If you visit in late summer or fall, be sure to enjoy some black or white truffles — it’s one of the best places to get them outside of Piemonte!