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An authentic Italy. That’s what you dream of when going, right?
We all wish for that unique experience, where you feel the connection to the place, the people and the past. Trinkets and tourists (well, other tourists) obscure that connection and allows only for a superficial encounter. Fortunately, there are still many such places in Italy. And Umbria is one one them.

It has maintained its heritage and kept its traditions live and well. Culture is alive and thriving in these petrified places of history. It’s a place of magic. You can sense it in the cobblestone, labyrinthical streets. You can feel it when you look out upon the landscape. C.S Lewis got it quite right when he named the enchanted Kingdom of Narnia after a place right here. Discover with us the 10 Most Enchanting Hilltop Towns of Umbria.

Assisi

Immortalised through Saint Francis of Assisi who was born here and started missioning in his 20ies in the beginning of the 13th century. Much like the story of Buddha, he was born as the son of rich family and spent a luxurious and care-free youth, only to receive a divine calling, urging him to give up his riches and live amongst the poor.

The UNESCO World Heritage town of Assisi is defined by the imposing basilica complex that bears his name as well as the many religious visitors, coming to pay homage to the gentle saint. If you arrive by car, there are not many other options than to park at the paid car parks below the city walls. Advantage is, that escalators will take you to the historic quarter, where you can stroll around and check out the other historic and religious buildings around town: Basilica di Santa ChiaraCattedrale di San RufinoChiesa Parrocchiale di Santa Maria MaggioreCasa di San FrancescoChiesa di Santo StefanoChiesa di S. Maria sopra Minerva (which is actually an old, Roman temple) and Abbazia di San Pietro. There are so many to choose from, but one that dwarfs the others in size and importance: Basilica of San Francesco with the cript and Sacro Convento.

There are so many sights which should be described in more detail, but we’ll have to save that for a feature article, because Assisi definitely deserves attention, also for its Roman, Medieval, Renaissance and Baroque sites and monuments. When you leave, be sure to pop by the equally impressive Basilica di Santa Maria degli Angeli only 10 minutes away in Porziuncola. Here, in the little chapel inside, St. Francis drew his last breath.

Gubbio

One of the northernmost towns of Umbria, Gubbio is perhaps not as much hilltop than hillside. It is only 4 kilometres from the Marche region’s border, and adorns the northern hillside of the upper Chiascio valley, offering amazing views as it sits sunbathed up the hills.

Even before you get out of your car at the (free on workdays) car park, you realize the historic grandeur of this smallish town as you eye the remains of the Roman Theatre just next to the car park. The ruins are free to stroll around, while you try to snap a picture of the hillside town with the ancient theatre in front. The historic architecture really is condensed here.

The WOW effect is brought about at Piazza Grande, just in front of Palazzo dei Consoli, originally built as the seat of government for the region and now functions as museum. This imposing 14th century palace bestows medieval grandiosity and a sense of solidity to the square, while on the other hand you have this amazing view to the town below and valley at your feet. You truly feel like you’re king of the world at this spot, and understand why this is one of the most majestic and audacious building projects carried out in the Middle Ages, bearing witness to the ambitious nature of Gubbio’s political power.

Stroll around town and check out the 12th century Cathedral, the medieval Loggia dei Tiratori and adjacent Church of San Francesco, the fabled Fontana del Bargello and the picturesque Ortobello quarter. And if you still have energy to burn, scale the mountainside of Monte Ingino to the 16th century Basilica di Sant’Ubaldo for a view that just IS a little better.

Narni

One of the northernmost towns of Umbria, Gubbio is perhaps not as much hilltop than hillside. It is only 4 kilometres from the Marche region’s border, and adorns the northern hillside of the upper Chiascio valley, offering amazing views as it sits sunbathed up the hills.

Even before you get out of your car at the (free on workdays) car park, you realize the historic grandeur of this smallish town as you eye the remains of the Roman Theatre just next to the car park. The ruins are free to stroll around, while you try to snap a picture of the hillside town with the ancient theatre in front. The historic architecture really is condensed here.

The WOW effect is brought about at Piazza Grande, just in front of Palazzo dei Consoli, originally built as the seat of government for the region and now functions as museum. This imposing 14th century palace bestows medieval grandiosity and a sense of solidity to the square, while on the other hand you have this amazing view to the town below and valley at your feet. You truly feel like you’re king of the world at this spot, and understand why this is one of the most majestic and audacious building projects carried out in the Middle Ages, bearing witness to the ambitious nature of Gubbio’s political power.

Stroll around town and check out the 12th century Cathedral, the medieval Loggia dei Tiratori and adjacent Church of San Francesco, the fabled Fontana del Bargello and the picturesque Ortobello quarter. And if you still have energy to burn, scale the mountainside of Monte Ingino to the 16th century Basilica di Sant’Ubaldo for a view that just IS a little better.

Todi

One of the northernmost towns of Umbria, Gubbio is perhaps not as much hilltop than hillside. It is only 4 kilometres from the Marche region’s border, and adorns the northern hillside of the upper Chiascio valley, offering amazing views as it sits sunbathed up the hills.

Even before you get out of your car at the (free on workdays) car park, you realize the historic grandeur of this smallish town as you eye the remains of the Roman Theatre just next to the car park. The ruins are free to stroll around, while you try to snap a picture of the hillside town with the ancient theatre in front. The historic architecture really is condensed here.

The WOW effect is brought about at Piazza Grande, just in front of Palazzo dei Consoli, originally built as the seat of government for the region and now functions as museum. This imposing 14th century palace bestows medieval grandiosity and a sense of solidity to the square, while on the other hand you have this amazing view to the town below and valley at your feet. You truly feel like you’re king of the world at this spot, and understand why this is one of the most majestic and audacious building projects carried out in the Middle Ages, bearing witness to the ambitious nature of Gubbio’s political power.

Stroll around town and check out the 12th century Cathedral, the medieval Loggia dei Tiratori and adjacent Church of San Francesco, the fabled Fontana del Bargello and the picturesque Ortobello quarter. And if you still have energy to burn, scale the mountainside of Monte Ingino to the 16th century Basilica di Sant’Ubaldo for a view that just IS a little better.