The Most Beautiful Towns in Umbria, Italy

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In the foothills of Mount Subasio, the walled town of Spello seduces architecture lovers and photography buffs with its winding medieval streets and crumbly old churches. The place certainly has history: founded by the pre-Etruscan Umbri people, Spello became a Roman colony in the 1st Century BC, and that legacy is still visible today. Consider the stunning sights, including the Porta Venere – a splendidly preserved Augustan-era town gate. Visit in summer when the streets and honey-coloured homes come alive with vibrant floral displays planted by the residents with painstaking care.

Among Umbria’s most beautiful hilltop towns is Orvieto, close to the border with Lazio, balancing on a volcanic butte above the scenic plains of the southwest. Its crowning glory is the cathedral, a triumph of 14th-century gothic that attracts crowds – chiefly for Renaissance painter Luca Signorelli’s awe-inspiring frescoes in the Chapel of San Brizio. Under the town is a riddle of Etruscan-era tunnels and grottos 2,500 years old, put to various purposes over the ages, from siege escape routes to wine cellars to World War II bomb shelters. They’re open to visitors, so try a guided tour.

On the shores of Lake Trasimeno, where Umbria meets Tuscany, the town of Castiglione del Lago is famous for its 13th-century Castello del Leone, whose lofty watchtowers reveal splendid views over glittery water to the countryside beyond. The town makes an ideal base for outings to water’s-edge villages and tranquil islands: the biggest, Isola Polvese, is home to the historic Church of San Guiliano and the beautiful Garden of Aquatic Plants, created by architect Pietro Porcinai in 1959. Each spring, the skies above Castiglione del Lago flutter colourfully into life during the Coloriamo i Cieli Festival, as hundreds of kites take to the air, along with leisurely hot-air balloons.

In Umbria’s northwestern reaches, Gubbio stands proud against the slopes of Mount Ingino. The town is celebrated for its rich cultural heritage – notice the ruins of a 1st-century Roman theatre as you approach. One of Italy’s oldest folklore festivals, La Festa dei Ceri, takes place in town every year on 15 May. Wander the steep, winding streets and you will, at some point, arrive at the stark, spreading central Piazza Grande, almost dwarfed by the crenellated medieval Palazzo dei Consoli with its neck-craning bell tower. Pause awhile: from here you have perfect panoramic views over Gubbio.

A few miles east of Umbria’s capital of Perugia rises the heart-stoppingly photogenic hilltop town of Assisi. It is famously the birthplace of Saint Francis of Assisi (1181-1226), patron saint of animals and the environment. The Basilica di San Francesco, built in his honour between 1228 and 1253, is probably the must-see while you’re her, and it remains an important Christian pilgrimage site to this day. Other sights include the Roman Temple of Minerva, built in the 1st century and immaculately preserved – testament to Assisi’s respect for its rich history. If time allows – and it really should – beautiful Mount Subasio Regional Park is a haven for nature lovers.

High on a hilltop above the winding Tiber, the pretty town of Todi is like a cartoonish cut-out in a child’s pop-up book. Narrow, cobbled streets meander slopingly, leading to beautifully preserved medieval monuments. Search for the Palazzo del Popolo, built in 1213, one of Italy’s oldest public buildings, now at home among cute cafes and boutiques. Strangely untouched by tourism, peaceful Todi presents a slice of real Umbrian life. While here, have a long lunch or dinner: culinary delicacies include slow-cooked pigeon flavoured with herbs, perfect with Grechetto di Todi, a dry white wine that has been made in the area for centuries.

Medieval Torgiano basks against horizons of olive groves and vineyards, a clear indication of what keeps the town busy (olive oil, wine production) when it’s not sleeping. The celebrated produce has given Torgiano worldwide fame, and if you’d like to find out more about its rich gastronomic history pop into the Museo del Vino and Museo dell’Olivo e dell’Olio. Catnip for gourmands, it’s also heaven for history buffs, with notable sights such as the postcard-perfect Torre Baglioni, a beautiful imposing tower on the edge of town, dating back to 1274.

With a colourful history, delicious cuisine and a singular setting in the foothills of the Sibillini Mountains, Norcia is firmly on the map for nature lovers, history buffs and anyone with a healthy appetite. At the heart of this picturesque town is the picture-book main square, Piazza San Benedetto, home to some of Norcia’s oldest buildings: notably the Castellina, a 16th-century fortress by Renaissance architect Vignola, and the beautiful Basilica di San Benedetto with its 14th-century gothic facade. And to eat? First and foremost it’s got to be a few Nero Norcia truffles and lots of local salumi.

Founded as a fortress in the 10th century by a Roman nobleman, Arrone is a lovely-looking hamlet on a hill in southern Umbria. It is divided into two distinct parts. Around the base is the newer Santa Maria quarter, home to the Chiesea di Santa Maria Assunta, a 15th-century church bearing head-turning frescoes by artists including Vincenzo Tamagni and Giovanni da Spoleto. As you ascend Arrone’s steep, meandering streets you’ll come to its oldest part, La Terra, where history reverberates about the encircling walls of this beautifully preserved medieval village.

In the heart of Umbria, Bevagna is a valley town between two rivers. Its location – on ancient Via Flaminia, the Roman road leading from Rome to present-day Rimini – has imbued it with history. The town square, Piazza Silvestri, has two sensational romanesque churches: small, understated San Silvestro and imposing San Michele Arcangelo, sentried by a majestic bell tower. Oenophiles and design-lovers have a treat in store a short drive northwest beyond town: Tenuta Castelbuono vineyard has a dramatic, carapace-like wine cellar, courtesy of Milan-based sculptor Arnaldo Pomodoro.

Here’s the very epitome of an Italian hilltop town, all terraced olive groves, crumbling stone walls and church towers, set in the southwestern corner of Umbria, not far from the city of Terni. According to some scholars, it may also be the oldest town in the region, dating back to around 1000BC. The polygonal masonry of its stone walls is thought to date back to the founding of the town, while original sections of Roman road are threaded through it. You’ll find plenty more history in the archaeological museum.

This labyrinthine medieval town in the foothills of the Apennines ticks all the boxes: squeezingly tight cobbled streets, sunny piazzas, buzzy little cafes and crumbling churches of honey-coloured stone, cool and cave-like on the inside, with ancient flaking frescoes. Cypress trees sprout up like fountains of green from behind tall stone walls. Unexpectedly, there’s a hulking 14th-century fortress on a hill overlooking the town. Until 2007 it was used as a prison. Now it is a museum dedicated to the history of Spoleto.

This beautiful medieval town on the Tiber is said by some to be the birthplace of the Renaissance (Florence may have something to say about that). In the north of Umbria, near the border with the Marche and Tuscany, it is certainly a work of art. The historic core is a warren of cart-width cobbled streets and hidden churches. The centrepiece is the Palazzo Vitelli alla Cannoniera, a 16th-century palace-turned-art gallery, containing extraordinary examples of work by Renaissance artists such as Raphael, Luca Signorelli and Andrea della Robbia.

So well-preserved are some of its historic buildings that if someone led you here blindfolded and whipped it away, you would swear you’d been teleported way back in time. Take the town’s official symbol, the immaculate Rocca di Umbertide: a medieval castle that formed the guarding entrance to the citadel. Other highlights include the church of Santa Maria della Reggia, an unconventionally octagonal building housing paintings by Niccolò Circignani; see, too, just beyond town, the Civitella Ranieri Foundation – a dramatic castle and artists’ residence.

By Umbria’s western boundary, on the slopes of Mount Mutali, this tiny town is all climbing lanes, worn stone staircases disappearing up through archways and around corners, and unexpected windows of views across the rolling countryside below. Dark alleyways are brightened by window boxes full of geraniums, and beautiful little terraced courtyards appear as if by magic. If it doesn’t have the box-office history to magnetise the crowds, then so much the better – hang around and enjoy this place all by yourself, far from the beaten path.
Alex Allen contributed additional reporting to this article.