We are finishing two weeks in Umbria, and enjoyed both Spoleto and Gubbio. Both are what I'd call larger hill towns. Spoleto has great access for visitors via escalators/moving walkways from parking lots at the bottom, and Gubbio has elevators to save visitors' steps. Each has restored ruins of a Roman theater with an associated archaeological museum, and each has an impressively large piazza facing either the duomo (Spoleto) or the fortified center of government (Gubbio).
However, there is much to be said for the smaller Umbrian hill towns, such as Spello (between Assisi and Spoleto) in which we stayed. I was fascinated by the Pinturicchio frescoes (of the Annunciation, Nativity and the young Jesus debating at the temple) in Spello's main church, for their interesting, even amusing, details, such as the realistic shepherds (one gap-toothed, another with a wonderfully craggy face), Mary seeming to pull Joseph away from involvement in the debate, echoing a girl restraining a boy from joining in, the beggars outside the temple, the young shepherdess caressing a lamb, and the artist's miniature self-portrait on a wall within one of the frescoes. Thanks to a 1978 restoration, the colors of are magnificent.
We also visited other small Umbrian hill towns, such as Trevi, Bevagna and our other favorite Montefalco, which has a 360-degree view of the Vale of Spoleto where its noteworthy wines are produced: the red Sagrantino, the sweet red Passito Sagrantino from semi-dried grapes, and the white Grechetto dei Colli Marani.