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Umbria Best Villages

Best Villages in Umbria

Take a look at our list of the most gorgeous villages in the beautiful region of Umbria.

There are many ways you can describe the region of Umbria: beautiful, historic, lush, verdant, mysterious. The list goes on. Lying in the very heart of Italy, it stands out from the rest of the country by being the only region without a coast; this has shaped its landscape, culture and history into something unique. The people of Umbria, for centuries, have taken advantage of what their abundant valleys provide, meaning you’ll encounter some of the most delicious produce and freshest food in all of Europe.

Hiding within these forested valleys are unimaginably beautiful villages known only to Umbrians. Away from the main cities, you’ll delight in the crowd-free and authentic experiences you’ll encounter here, where you can enjoy a taste of true Umbria. Read on to discover the most beautiful towns and villages you can discover on our Umbrian cycling holidays.

Umbria Best Village Cycling Tour


Originally an island in Lake Trasimeno, Castiglione-del-Lago has grown over the past millennia to join the mainland and become a peninsula. Its strategic position as a crossroads between the north and south has meant it’s the sight of many historical and destructive battles. In antiquity, the Romans and the Etruscans fought here, and in medieval times, there were many conflicts between the Umbrians and Tuscans.

Within the town, there is a magnificent castle known as the ‘Fortress of the Lion’ which was built by Emperor Frederic II in 1247. Remarkably well-maintained, its walls still line the bank of Lake Trasimeno. With fantastic views of the lake and impressive historical sights, Castiglione-del-Lago is undoubtedly one of the best villages in Umbria.

Umbria Castiglione-del-Lago


Located on the border between Tuscany and Umbria, the ruins of Pierle Castle sit proudly at the top of a hill. Like almost every building in Italy, there is a deep and fascinating history associated with it; built and rebuilt multiple times, at one point it was torn down by a member of Florence’s Medici family to prevent highwaymen from seeking shelter in its walls.

Today, the castle and surrounding houses have seen renovation efforts to maintain the beauty of the area. Hopefully, this will mean the site can be viewed by visitors for years to come, as it’s such a wonderful example of Tuscan-Umbrian history. On our cycling escapes to the region, you’ll have the chance to see this fort for yourself.

Umbria Pierle

Lisciano Niccone

With a cypress-lined avenue leading to the village, you’ll instantly recognise this scene as one of the most photographed places in Italy, and for good reason! Winding its way along the hills, there’s something so captivating about the entrance to Lisciano Niccone. In the village, take a walk amongst its cobbled streets and visit the impressive castle.

There are many castles on the Umbrian and Tuscan border, highlighting just how far back the rivalry between these two regions stretches. Cycling between the two regions is often our favourite way of experiencing Tuscany and Umbria, as it helps to paint a clearer picture of how these two peoples differ, adding to the wider Italian culture.

Umbria Lisciano Niccone


A member of the I Borghi più Belli d’Italia (the most beautiful villages of Italy) association, Montone is recognised as one of the most beautiful villages in the whole of Italy. This walled settlement sits at the top of a hill, surrounded by lush Umbrian valleys. The buildings and cobbled streets date back centuries and mirror the long and fascinating history of the village.

Montone, historically, has always sat under the watchful eyes of the Papacy to the south. The majority of this period featured the Fortebracci family ruling the city. Their presence can still be seen in countless buildings and streets named after them. Cycling here, enjoy fantastic scenery as you approach the town; Montone rests at the top of a proud hill. 

Umbria Montone


We’ve saved the best till last on our list: Spello is impossibly beautiful, with ancient streets lined with blooming flowers in a rainbow of colours. There are so many flowers in this town, that it has become famous as a result! People flock to see the display put on by the everyday citizens who just have a passion for gardening.

The town is another member of the I Borghi più Belli d’Italia, and you’ll easily see why when you visit here. The old walls of the town still run around the settlement, giving it a timeless feel that immediately transports you back to medieval times. Take a wander through its streets and try not to take too many photos (we know it’s hard to resist).

Umbria Spello

For more information on the most beautiful villages in Umbria, call our cycle experts today on 020 7471 7760.

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