Italy’s Umbria region is a wonderland of historic villages, scenic valleys, delicious food, and peaceful rural retreats. Skip the crowds of Tuscany and enjoy these four medieval towns in Umbria; they’re perfect for off-the-beaten-path exploration!
Happy New Year, everyone! (Is it still ok to say that on January 9? My sources disagree.) Either way, I hope you all had a lovely holiday season and that 2024 is treating you well so far.
I hope you’re ready, because 2024 is going to be the year of Italy on Full Life, Full Passport! I have so much that I’m excited to share with you following M’s and my anniversary trip last fall, and I want to start with the region that absolutely captured our hearts: Umbria.
Located smack-dab in the middle of the country, Umbria is Italy’s only landlocked region. It offers all the benefits of Tuscany – medieval towns, world-class wineries, delicious cuisine, beautiful views, excellent hospitality, and more – but with a fraction of the tourist traffic. In fact, M and I spent a whole afternoon exploring the historic center of Gubbio (the first town I suggest below and our favorite of the four) and only heard English spoken once.

One of the best things to do in Umbria is to explore the medieval hill towns that are scattered across the region. Built defensively on high ground and mountain slopes, these stone cities have stood since the Middle Ages and retain much of their charm. We spent almost all of our time in Umbria bouncing from one beautiful village to the next, and I can’t wait to go back and see more.
Today, I’m sharing four of the best medieval towns in Umbria. There’s Gubbio, with its “bird cage” cable car and amazingly colorful Saint Ubaldo Day festival; Spoleto, whose hilltop fortress that offers panoramic valley views; the golden alleyways of Spelloย overflowing with flowers; and Assisi, a cherished pilgrimage site and home to a breathtaking cathedral. And whether you choose to visit one or all, I have no doubt that they will be places you’ll never forget.
Gubbio

The first medieval town that should be on your Umbria list is undoubtedly Gubbio. Nestled in a valley in northeastern Umbria, Gubbio spills up the slope of Monte Ingino in a tumble of stone buildings and terracotta rooftops. And despite being a Middle Ages powerhouse, the hometown of a bonafide saint, and the location of one of Italy’s most colorful festivals, Gubbio is still blissfully off-the-beaten path.

Many of Gubbio’s historic buildings are made of the same gray limestone, giving it a uniform look that adds significantly to the city’s charms. The best way to appreciate the city is to just wander its winding streets, letting yourself get lost down alleyways and scaling staircases in search of better and better views.


While undeniably picturesque, I loved that Gubbio feltย lived in. Tiny cars buzzed through the narrow streets or parked in front of centuries-old houses. And everywhere we went, people were speaking Italian, not English to appeal to a tourist crowd.



One of the most fun and unique things to do in Gubbio is to ride the Funivia Colle Eletto. This cable car whisks you to the top of Monte Ingino, where the Basilica of Sant’Ubaldo competes with the commanding views out over Gubbio to see who can most impress you.

As longtime readers know, I have a love-hate relationship with cable cars. I love the views I find at the top, but the thought of being held aloft by nothing but a thin metal cable is enough to set my heart racing. It didn’t help matters that the Funivia features what our bed and breakfast host refers to as “bird cages” – open metal baskets that hold up to two people for the ride up the mountain.
(You know you’re in for a good time when someone tells you that the attraction they’re recommending “would never be allowed in the States.”)

Surprisingly, however, I felt more secure in these baskets than I have in many larger, heavier cable cars. The ride was smooth, the basket was sturdy, and it certainly helped that we never gotย too high off the hillside. (“I could probably survive this fall with a few broken bones” is always a better thought than “They would never find my body if this thing went down.”)
Our ascent only took six minutes, and the scenery kept getting better the higher we went. Soon enough, we were leaping out of the baskets and making our way along a dirt path toward the church.ย

The church is pretty inside, with the added bonus of having the eponymous saint’s body on display. Dead since 1160, Saint Ubaldo now rests in prominence in a glass and gold coffin just behind the altar.

Another of the treasures housed in the church are the three massive wooden “candles” used in the annual festival honoring St. Ubaldo, Festa dei Ceri. Thirteen feet high and weighing eight hundred pounds apiece, these massive structures are affixed with statues of saints and raced by teams from the Piazza Grande to the top of the mountain – a distance of 2.5 miles!
(Spoiler alert: St. Ubaldo always wins.)

The festival is a massive celebration, full of color and revelry, and if you’re anywhere in Italy in mid-May, you should make your way to Gubbio to witness it! The video below is not mine, but should give you a good idea of the madness and fun that ensue on the day of the festival:
For those of us not racing the statue of a saint to the top of a mountain, the beautiful views out over the valley are excitement enough. Near the church is Ristorante La Cia, the perfect spot to grab a drink or a bite to eat while soaking in the scenery.


Other worthwhile activities in Gubbio include:
- Visiting the ruins of a first-century Roman ampitheater.
- Touring the Palazzo Ducale, an art museum housed in a 15th-century palace with an impressive courtyard.
- Admiring the Piazza Grande. It was closed for earthquake reinforcement while we visited, but it’s a major landmark in the city. There are great views to be had out over the valley.
Tips and Practical Information for Gubbio
- Although there’s no need to rush yourself through Gubbio, it is not a large town. You can easily see the sights in a day or less.
- The Teatro Romano parking lot (parcheggio) was very convenient for entering the historic part of Gubbio. You’ll find it on Viale Teatro Romano near Viale Parruccini, right near the ruins of the Roman theater that give the lot its name.
- The Funivia costs around $7 per person and tickets can be obtained onsite. Hours change seasonally, and operations pause for an hour and a quarter during lunchtime on non-holidays. Make sure to check the website for the most up-to-date information.
- While they will slow the Funivia to allow certain passengers to board, be aware that the baskets generally don’t stop and you’ll need to hop on while they’re moving. An attendant will be there to help and direct you.ย
- Make sure to try crescia, a regional flatbread that can be enjoyed with any number of toppings. (Meats, cheeses, and nutella are the obvious best options.)
- The gelato at La Gelateria is not to be missed!
Spoleto

The next medieval Umbrian town on your list should be Spoleto. Once a Roman colony, the town is located in southern Umbria in the shadow of the Apennines. An imposing, six-towered fortress looms over the city, and scattered through the town are Roman relics, historic churches, delicious restaurants, and other great finds.ย
One of the more interesting structures in Spoleto is the Torre dellโOlio, or Tower of Oil, on what is now Via Porta Fuga. Descending through an ancient city gate along a pedestrian walkway lined with shops and restaurants, it’s easy at first to miss this narrow, 13th-century tower.ย

What might seem like a benign enough name actually comes from the medieval practice of using the tower to pour boiling oil on enemies trying to attack the town. Legend has it that boiling oil was one of the weapons used in the defense of Spoleto during Hannibal’s invasion, which helped to weaken the Cathaginian forces such that they were unable to capture Rome.
Nowadays, the Torre dell’Olio is the tallest tower in the city and has been incorporated into the surrounding buildings. We managed to walk in its shadow without any gruesome showers and made our way back through the city gate, orย Porta Fuga.

Part of the beauty of Umbria comes from its many hills, but they also can be the bane of any traveler looking to do a lot of on-foot exploration. Fortunately, Spoleto has got you covered. Underneath the city is a system of moving walkways – similar to what you’d find in an airport – that can take you the whole way from the bottom of the town to the fortress at the top of the hill (and back down, if you wish). They’re completely free to use, have multiple access and exit points, and are wonderfully effective at saving your quads from a long, grueling climb.ย

We accessed the percorso meccanizzato directly from the garage where we parked and used it to quickly make our way to the highest point in town: the Rocca Albornoziana.

Constructed in the 14th century on the orders of Pope Innocent VI, the fortress is impressive for a reason. It was built to demonstrate the power and authority of the papacy in the region, and also as a military stronghold for the Church.



Today, it’s worth a visit for the sweeping views across the valley…

… and of the ten-arched Ponte delle Torri that stretches across a gorge.

Also dating to the 1300’s, this bridge was built on what remained of a Roman aqueduct. The sheer size of it is awe-inspiring, especially when you consider how long it has stood. The bridge was still closed when we visited due to damage from the 2016 earthquake, but it’s best appreciated from other viewpoints anyway.ย
A short walk back into the town of Spoleto quickly brings you to my favorite spot in the city: the Duomo di Spoleto (Spoleto Cathedral, officially the Cattedrale di Santa Maria Assunta) and its lovely piazza.
I’ve visited many historic churches across the globe, but there was something special about the location of this one. Approaching the area along Via Aurelio Saffi, you suddenly find yourself at the top of a long set of wide, low stairs that sweep down to the square. Your eye is immediately drawn to the cathedral at the opposite side, and descending the staircase feels like joining a throng of worshippers all making their way toward the church.

The piazza is large and open, with the pale color of the stone standing in sharp relief against the greenery of the hillside on which the church sits.ย


Above a Renaissance-era portico (they loved their porticos!) sit multiple rose windows and a Byzantine mosaic.ย

The church is free to enter, and it’s well worth checking out the interior.ย

Particularly striking are the colorful frescoes in the apse at the front of the church, where moments in the life of Mary, the mother of Jesus Christ, are beautifully detailedย

Leaving the cathedral behind, there are plenty of vibrant and interesting streets to wander in Spoleto. The town is full of narrow alleyways, lovely courtyards, hole-in-the-wall tourist shops, and more delights. Plus, if you used the motorized walkway to get to the fortress, it’s all downhill from here!





Other worthwhile activities in Spoleto include:
- Checking out the Casa Romana, or Roman House, to see a well-preserved example of a Roman villa, complete with floor mosaics.ย
- Visting the small museum about the Duchy of Spoleto inside theย Rocca Albornoziana.
- Attending theย Festival dei Due Mondi (Festival of Two Worlds, but also known simply as the Spoleto Festival). This massive, multi-week performing arts festival is held each summer and continues to be a must-do activity if you’re in the area.
Tips and Practical Information for Spoletoโ
- There’s a parking garage called Parcheggio della Posterna that makes a great jumping-off point for visiting Spoleto. From there, you can easily access the Torre dell’Olio and walk up through the historic town, or you can hop right on the underground moving walkways (Percorso Meccanizzato) and head straight to the fortress at the top of the hill.
- The Percorso Meccanizzato does not run 24/7, so make sure to check the hours posted at the entrances if you’re visiting very early or very late.
- If you’re driving away from Spoleto, make sure to travel north along Via Flaminia for great views of the Rocca and Ponte delle Torri. You can also catch a nice glimpse of the fortress from the Chiesa di San Pietro, a church just outside of town.ย

Spello

After Gubbio, pretty Spello was undoubtedly our second favorite medieval town in Umbria. There is so much to love about this little village, which comes flowing down a hill in a run of pale yellow stone buildings. An ancient wall surrounds the historic center, and everywhere you look there’s an alleyway begging to be explored.
An endearing quirk of Spello is that those alleyways are often filled with greenery, as local residents crowd the streets with flower pots, hanging baskets, and window gardens.



Walking up Spello’s main street, Via Camillo Benso Conte di Cavour, takes you past dozens of tempting restaurants, artisan shops, and wine bars (enotecas). It requires a tremendous amount of self control not to stop in and sample something at every delicious-looking place along the way.

There also are plenty of alleys to dart down, leading to pretty courtyards, charming streets, and other hidden nooks and crannies of historic Spello.


If you continue uphill through town, you’ll be rewarded with burning quadriceps and impressive scenery. The hills in Spello can be pretty steep (I was definitely missing that moving walkway in Spoleto), but the panoramic views of the Umbrian countryside are well worth it.

Climbing higher and leaving the main street (which narrows and changes names numerous times after the Piazza della Republica) also allows you the chance of finding some space to yourself away from other visitors. The small size of Spello’s historic center means that tourists – and the shops and restaurants catering to them specifically – are more noticeable here. Thankfully, Spello is so charming that it’s hard to mind it being a bit touristy. The village still feels real and lived-in, and even more so if you wander less-traveled corners of it.


Other worthwhile activities in Spello include:
- Visiting theย Villa dei Mosaici di Spello, a small museum showcasing Roman mosaics that were discovered in 2005.
- Take in the views from the Belvedere Cappuccini scenic overlook.
- See the famous frescoes inside the Chiesa di Santa Maria Maggiore.
Tips and Practical Information for Spello
- There is a small public parking lot on Via Martin Luther King that is very convenient for accessing the old town. It’s also adjacent to the Villa dei Mosaici di Spello.
- If you’re looking for a meal spot, La Cantina de Spello offers tasty food in an atmospheric and cozy stone cellar.
- Spello’s small size and close proximity to Spoleto and Assisi (below) mean that a stop here can easily be combined with a visit to either or both larger towns.ย
Assisi

No list of medieval Umbrian towns would be complete without Assisi, perhaps the most famous city in the region and a major pilgrimage site for Catholics from around the world.ย
The town’s name is practically synonymous with St. Francis, who continues to be one of the most famous and venerated holy men in the history of the Catholic Church. During his life at the turn of the 13th century, Francis embraced the ideals of humility, poverty, and care and compassion for the less fortunate. Today, thousands visit Assisi to walk in St. Francis’s footsteps and pay their respects at the saint’s tomb, but there’s plenty to see and appreciate here even if you’re not a Catholic.
Catholic or not, the first among the must-see sights in Assisi is the massive Basilica di San Francesco, or Basilica of St. Francis.ย

This 13th-century complex dominates Assisi’s skyline and is actually two churches in one. The newer Upper Church is covered in an impressive cycle of frescoes chronicling Francis’s life. Below it, the Lower Church is also opulently adorned with frescoes, and you can descend through it into the crypt where the saint is buried. It’s a quiet, contemplative place, with plenty of faithful bent in prayer.
You could easily spend hours examining all the artwork in the Basilica, visiting the libraries and archives in the Sacro Convento (the Sacred Convent), and meandering through the Museum of Treasures, which is filled with religious relics, artifacts, artwork, and vestments.ย
But there’s more to Assisi than the Basilica! Stepping away from the complex – and the glut of souvenir and religious paraphernalia shops you’ll find in its immediate vicinity – you’ll find plenty of picturesque streets, scenic views, and other historic landmarks to occupy your time.

Like each of the previous three medieval Umbrian towns, this is a place to just enjoy wandering. A perfect afternoon can be spent trekking through the hilly, ancient streets, wondering about the lives of the generations who have called this place home and ducking into the occasional artisan shop or cafe along the way.



And when you reach a break in all those pretty stone buildings, the views out over the valley are lovely, as well.

Near the center of the city, the Piazza del Comune is a wide open square around which the secular administration of Assisi took place in the Middle Ages. The feeling of power is palpable here, especially after exploring smaller towns like Spello. Statelyย palazzos, an ornate fountain, churches, and museums surround the square, and melodies from street musicians waft through the air.

You’ll even spot the facade of a first-century Roman temple, the Temple of Minerva, with its impeccably preserved columns.

The piazza is also a great place to pause and people-watch; any number of cafes are ready to serve you an aperol spritz to enjoy as you observe the busy happenings in the square. With people visiting Assisi from all over the world, there’s always something interesting to see.

Many people visit Assisi on day trips from places like Rome, meaning that the city empties out in the late afternoon when the tour buses leave. If you’re able to stay in the city as dusk falls, you’ll experience a truly magical time.

The setting sun paints a rosy glow on the old streets and buildings, making dusk a gorgeous hour to wander the now largely-empty streets.



If you can, grab dinner in Assisi, as well, preferably at a place like Le Terrazze di Properzio that looks out over the city and valley below.


And don’t forget to take a few moments to admire the Basilica lighting up the night. It’s a beautiful final glimpse of this special city.


Other worthwhile activities in Assisi include:
- Checking out any of the number of other important churches in the town, including the Basilica di Santa Chiara, the Cattedrale di San Rufino, and the Basilica di Santa Maria degli Angeli.
- Checking out the Foro Romano, the ruins of an ancient Roman forum.
- Visiting the Eremo delle Carceri, a monastery set among the caves where Francis and his followers prayed and meditated.
- Trek down to St. Francis’s Grotto, where he lived for a time.ย
- Admire the panoramic views from the Rocca Maggiore fortress above the city.
Tips and Practical Information for Assisi
- Parcheggio Saba Giovanni Paolo II is a great place to park, as it’s only a short walk away from the Basilica.ย
- Ensure that you make reservations in advance for Le Terrazze di Properzio, especially if you want a seat with a view.
- While you can certainly see Assisi in a day, there is also enough to do here to fill a couple of days.ย
- Book accommodations well in advance if you’re planning to stay overnight in Assisi, especially around religious holidays.
Where to Stay to Visit Medieval Towns in Umbria
For our time in Umbria, we chose to stay at La Cuccagna, an agriturismo (farm stay) about halfway between Perugia and Gubbio. And let me tell you, three nights were far too few at this special hilltop bed and breakfast.

La Cuccagna embodies everything that makes Umbria wonderful: exceptional hospitality, good food, rustic charm, sensational views, and a relaxed pace of life. Sal and Sarah are experts in the region and all too happy to share their wealth of information to help make your sightseeing great. (I owe much of this article to them, thanks to their unfailing advice while we were visiting!)


Please note that you will need a rental car to stay at La Cuccagna, as part of its appeal is that it’s located well outside of any town. But chances are you’ll want a rental car anyway while visiting Umbria – it makes accessing all those gorgeous medieval towns so much simpler!


In Conclusion
While this article contains four excellent options for visiting medieval towns in Umbria, there’s so much more to explore! Make sure to allow yourself plenty of time in this lovely, under-the-radar corner of Italy. You won’t regret it!



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