Nestled in the foothills of Mount Subasio is the picturesque walled town of Spello where winding medieval streets and age-old churches charm history buffs and architecture fans alike. Founded by the ancient Umbri, Spello was later colonized by Romans whose legacy can still be seen in sights like Porta Venere – a splendidly preserved Augustan-era town gate. Visit in summertime when Spello’s streets and honey-hued homes come alive with vibrant floral displays planted by locals.
Undoubtedly one of Umbria’s most beautiful hilltop towns, Orvieto – close to the border with Lazio – sits high atop a volcanic butte overlooking the scenic plains of the Umbrian southwest. The town’s crowning glory is the magnificent Orvieto Cathedral, the 14th-century Gothic jewel known for its vibrant facade and Renaissance painter Luca Signorelli’s awe-inspiring frescoes in the Chapel of San Brizio. Below Orvieto lies a magical myriad of Etruscan-era tunnels and grottos variously used as wine storage, World War II bomb shelters and a means of escaping sieges during their 2,500-year history and open to guided tours.
Located on the shores of Lake Trasimeno where Umbria meets Tuscany, Castiglione del Lago is the site of the magnificent Castello del Leone, a fortress built in the 13th century, whose lofty watchtowers offer incredible views of the lake and surrounding countryside. The town is an ideal starting point for exploring Lake Trasimeno’s islands, the biggest of which, Isola Polvese, is part of a scientific and educational park. It is home to sites of historic interest like the Church of San Guiliano and the beautiful Garden of Aquatic Plants, designed by architect Pietro Porcinai in 1959. Each spring, the skies above Castiglione del Lago become a colorful canvas when the Coloriamo i Cieli Festival sees hundreds of kites and hot air balloons take to the air.
Over in Umbria’s northwestern reaches is Gubbio, a charming town built into the steep slopes of Mount Ingino, known for its rich history and culture. Approaching the town, the ruins of a Roman theater built during the 1st century greet visitors while a walk through its steep, winding streets leads to the breathtaking Piazza Grande, a central square with panoramic views over the pretty town that also houses the imposing 14th-century Palazzo dei Consoli. Get a taste of Gubbio’s cultural heritage at La Festa dei Ceri, one of Italy’s oldest folklore festivals.
Just a few miles east of Umbria’s capital Perugia, the beautiful hilltop town of Assisi is best known as the birthplace of Saint Francis of Assisi, the patron saint of animals and the environment. The Basilica di San Francesco, built in St Francis’ honor between 1228 and 1253, is one of Assisi’s must-visit sights and a UNESCO World Heritage Site that remains an important Christian pilgrimage site today. Sights like the perfectly preserved Temple of Minerva built by Romans in the 1st century are testament to Assisi’s respect for its rich history, while the beautiful Mount Subasio Regional Park is a haven for nature lovers.
Perched on a hilltop high above the winding River Tiber, the pretty town of Todi is like something straight out of a fairy tale. Narrow, cobbled streets meander its hilly terrain and lead to beautifully preserved medieval monuments like Palazzo del Popolo; built in 1213, this is one of Italy’s oldest public buildings, positioned alongside cute cafes and boutiques. Largely untouched by tourism, Todi offers a real slice of peaceful Umbrian life; while you’re there make sure you try local culinary delicacies like slow-cooked pigeon flavored with herbs, and Grechetto di Todi, a dry white wine made in the area for centuries.
Surrounded by seemingly endless olive groves and vineyards, it’s clear that olive oil and wine-making are central to the sleepy medieval town of Torgiano’s character. Indeed, the town’s celebrated produce has gained worldwide fame and visitors can learn more about Torgiano’s rich gastronomic history at the Museo del Vino and Museo dell’Olivio e dell’Olio. In addition to being a haven for gastronomes, Torgiano is one for the history buffs too and home to notable sights like its iconic Baglioni Tower, an imposingly beautiful guard tower dating back to 1274 located on the edges of this charming medieval town.
Norcia’s enviable location nestled in the foothills of the Sibillini Mountains, its rich history and delicious local fare have made it a must-visit destination for nature lovers, history buffs and foodies alike. The beating heart of the picturesque town is undoubtedly its beautiful main square, Piazza San Benedetto. Here, you’ll find some of Norcia’s oldest buildings, from the Castellina – a 16th-century fortress designed by noted Italian Renaissance architect Vignola – to the beautiful Basilica di San Benedetto with its 14th-century Gothic facade. While you’re there make sure to try the world-famous Nero Norcia truffles and local salumi.
Founded as a fortress in the 10th century by a Roman nobleman, Arrone is a picturesque hillside hamlet located in Umbria’s southern reaches, divided into two distinct parts. Around the base of the town is the newer Santa Maria quarter, home to the Chisea di Santa Maria Assunta, a 15th-century church featuring beautiful frescoes painted by artists including Vincenzo Tamagni and Giovanni da Spoleto. Ascending Arrone’s steep, meandering streets leads to its oldest part, La Terra, where the town’s history comes alive in its beautifully preserved medieval walled village.
Nestled in the very heart of Umbria, Bevagna is a charming valley town nestled between two rivers bursting with history thanks to its location on Via Flaminia, an ancient Roman road leading from Rome to present-day Rimini. Bevagna’s town square, Piazza Silvestri, is home to not one but two stunning romanesque churches – the small, understated San Silvestro and the more imposing San Michele Arcangelo with its majestic bell tower. A short drive northwest of town is a treat for oenophiles and contemporary art lovers alike: discover Tenuta Castelbuono, a vineyard featuring a dramatic carapace-like wine cellar imagined by acclaimed Milan-based sculptor Arnaldo Pomodoro.