The medieval Ponte delle Torri aqueduct and the Duomo's Filippo Lippi frescoes anchor a town known beyond Umbria for the Festival dei Due Mondi. Montefalco's cellars sit half an hour west.
Known as the City of the Ceri, Gubbio's Gothic Palazzo dei Consoli holds the Eugubine Tablets, bronze plaques inscribed in the ancient Umbrian language. Break the drive north with a stop in Torgiano.
Pours: Torgiano Rosso Riserva DOCG, Torgiano DOC Bianco
A hilltop art town ringed by three concentric walls, built around Piazza del Popolo and the Renaissance Temple of Santa Maria della Consolazione. The Colli Martani Grechetto zone sits just north toward Cannara.
Pours: Colli Martani DOC Grechetto, Colli Martani DOC Sangiovese
Norcia gave its name to norcineria, Umbria's cured-pork tradition, and sits below the Piano Grande basin famous for the Castelluccio lentil harvest and a late May to June wildflower bloom.
Pours: Montefalco Sagrantino DOCG, Montefalco Rosso DOC
Ferries from Tuoro, Passignano, or Castiglione del Lago cross to Isola Maggiore, a village known for Irish crochet lace. Trasimeno's Gamay and Grechetto producers ring the lakeshore on the way there.
Pours: Colli del Trasimeno DOC Rosso, Colli del Trasimeno DOC Bianco
Known as the dying town for the erosion undercutting its tuff spur, Civita draws visitors across a footbridge to the Belvedere and Piazza San Donato, just over the border in Lazio.
Pours: Orvieto Classico DOC, Orvieto DOC
A UNESCO World Heritage hill town for the Basilica of Saint Francis and its Giotto and Cimabue fresco cycles. Pair a morning in the basilica with an afternoon stop at a Bevagna-side Sagrantino producer on the way back.
Pours: Montefalco Sagrantino DOCG, Montefalco Rosso DOC