5 Umbria Hill Towns

Medieval Monuments and Great Views

Although people often associate hill towns with Tuscany, the neighboring region of Umbria has its fair share of picturesque medieval towns perched on hills. Most of these hill towns still have medieval, or even Etruscan, walls surrounding the old town and stunning views of the countryside below and Etruscan or Roman remains.


Orvieto is one of the easiest hill towns to visit as it has a train station just below the old center and easy access from the A1 autostrada. The town makes a stunning sight, dramatically perched on a cliff. Orvieto’s top sight is its 14th century cathedral, with its shiny mosaic facade. One unusual sight is Saint Patrick’s Well, with double spiral staircases that run along the sides of the well without meeting. Below the town, passageways have been dug into the cliffs, some in use since Etruscan times. Surrounding vineyards produce Orvieto DOC white wine. While Orvieto is easy to visit as a day trip from Rome, it’s also a great place to spend a night or two.

orvieto cathedral photo
Orvieto Cathedral


Assisi is famous as the home town of Saint Francis and the Saint Francis Basilica that holds his tomb as well as the famous fresco cycle, the Life of Saint Francis, painted from 1296 to 1304. From the Basilica, a walking path leads down through the Saint Francis Woods. Also in the walled medieval center are Roman ruins, medieval sites, and museums. The town is also known for Calendimaggio, a big medieval event held in early May. Assisi can be reached by bus from the train station in nearby Santa Maria degli Angeli, whose church houses the tiny Porziuncola chapel where Saint Francis worshiped and the Cappella del Transito with the cell where St Francis died in 1226.

assisi apartments view
View from our apartment at Brigolante Guest Apartments, Assisi


Gubbio is a well-preserved and picturesque hill town with one of the oldest medieval centers in Umbria. Its compact historic center holds a good selection of medieval, Gothic, and Renaissance buildings. Below town is a 1st century Roman amphitheater where summer performances are held. Above town is an old abbey and remains of a fortress, reached by a cable car.Gubbio holds a huge candle race, Festa dei Ceri, May 15 and it claims to have the world’s largest Christmas tree, made of lights decorating the slope of Monte Ingino.

gubbio fountain photo
Fountain and Piazza in Gubbio, Umbria


Spoleto, one of the largest towns in southern Umbria, is best known for the Ponte delle Torri or Bridge of Towers, spanning the deep gorge. Near the bridge is the Rocca, a medieval fortress that sits above the town. Spoleto has a good selection of Etruscan, Roman, and medieval sites. San Salvatore, an ancient Longobard Church, is part of a UNESCO World Heritage site. Spoleto is also known for its July performing arts festival held in historic churches, the fortress, and the Roman theater.

  • Good restaurant and hotel options make Spoleto a good place to stay for a couple of nights or more. Find a hotel in Spoleto


Todi, one of the smaller hill towns, overlooks the Tiber River. Sights, mainly clustered around Piazza del Popolo, are close together making it easy to see the town in a couple of hours but you can easily linger longer, enjoying the views and the small town ambiance. Todi is about half an hour by train from Perugia so can be visited as a day trip but it makes a peaceful base for visiting southern Umbria, especially if you’re traveling by car. Grechetto di Todi, a white wine from Umbria, is produced in the surrounding vineyards.

todi photo
The Umbria Hill Town of Todi by James Martin

See our Map of Umbria showing top places to go

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5 Umbria Hill Towns originally appeared on MarthasItaly.com , updated: May 10, 2023.