Medieval Hilltown Gems

Enjoy your stay in one of our comfortable apartments – but do get out, too, to explore our town as well the hilltown wonders of Umbria, northern Latium, Tuscany, and the Marches. How long to stay? A lifetime. Pino and I have been discovering Italy’s wonders together for over thirty-five years and we’ve barely scratched the surface! Our Umbria, “Italy’s green heart” is wondrous all year round: read about each month in Umbria on the CALENDAR page. I do hope you will stay long enough in the Assisi area to explore at least the Umbrian hilltown highlights, ie, the hilltowns indicated in red in my notes which follow.




A thirteenth-century historian wrote of the Basilica di San Francesco: “no more beautiful monument to the Lord has yet been built.” Frescoed with the greatest frescoes in the world of the late 13th-century and early 14th- century, this three-level Basilica built to house the body of St. Francis of Assisi leaves one open-mouthed. Far more than one visit is needed. A couple days are needed just for Assisi’s monuments and many more to discover all the hidden wonders of the backstreets.And you’ll need to take time to meet a few of our “locals”.

I’ll tell you all about the best places to taste Umbrian cuisine and savor our prized wines, as well. The artisan work of the Assisi area tempts visitors: olive wood, textiles, ceramics. Many artists live and work in our town, too: ceramic artisans, artists of watercolors and oil, print-makers, terracotta artisans, book-binders. Happy to connect you!

Assisi Memorable Moments:


Spello view

Like Assisi, nearby Spello is built in the pink limestone of Mt. Subasio which backdrops both of these medieval hilltown gems. Great Renaissance artist, Pinturicchio, frecoed masterpieces in the Spello cathedral but modern personalities are leaving their marks on Spello, too: inspirational Franciscan friar, Brother Paul (who has lived a contemplative life alone for over twenty years), Elvio who paints masterpieces on the detached plaster from ruined farmhouses, naif painter Paolo, textile artisan, Paola, and Roberto and family who offer over-the-top wine-tastings and olive-oil tastings. Spello’s backstreets enchant, especially from spring to late summer, when in full flower….and don’t miss nearby Collepino (pop. less than 20)!

Spello Memorable Moments:

  • Sixty days after Easter for the Feast of Corpus Domini, the Spellani create over eighty astounding floral tapestries to welcome the Host (Christ) carried by the bishop throughout the winding medieval alleyways of the town. The Infiorate festival of Spello must truly be seen to be believed.



The early Romanesque churches, the 1st-c. A.D mosaics of the Roman baths, an 18th-century jewelbox of a frescoed theater – to name a few – certainly make Bevagna worth a visit.But so do Simone’s cooking at his wine-cellar restaurant, the simple baked goods of the Polticchia family, the tasting of pecorino (sheep’s milk) cheeses and Umbria’s top prosciutto, capocollo and more with Rosita and Marco at their famous butcher shop.

Bevagna Memorable Moments:


Montefalco: “the balcony of Umbria” (credits)

Called “the balcony of Umbria”, medieval Montefalco overlooks rolling hills of olive groves and vineyards where the famous Sagrantino grapes are cultivated. Famous for its wines and textiles, Montefalco also boasts a superb art museum, housed in a 13th c. Franciscan church as well as an Augustinian convent with astonishing relics of the town’s 14th-century Saint, Clare of Montefalco. Delightful restaurants along the main street tempt the visitor.
Montefalco Memorable Moments:

  • In September, the Montefalco Wine Week festival animates the streets and piazzas. At the end of May, drop into the Montefalco wineries in the surrounding countryside during the “Open Cellars” festival.
  • Bulls run not only in Pamplona, but also in Montefalco – in August when la Fuga del Bove festival takes over the town.
  • In November and December, taste the newly-pressed olive oils at Montefalco olive oil mills during the Open Olive Mills festival



Not many tourists head to Foligno, simply because there is so very much to see in Umbria and other better-known towns (and yes, more lovely, too) draw the visitors.
But if you’ve already visited Bevagna or Montefalco or Spello and you’re on your way to Spoleto, make a stop. If you have a free day in Assisi, hop a train for the 25-minute ride to Foligno.

Always an important rail center for central Italy, with repair and maintenance yards here, Foligno was heavily bombed by the Allies in World War II. The regular street plan of the center is evidence of its Roman origins though very little remains of its ancient past and only traces of its medieval history – but a most splendid one: Palazzo Trinci. Residence of the noble Trinci family of Foligno from the 14th- century to the mid 15th- century, the palace houses an archaeological museum and the civic picture gallery. The façade was redone in Neoclassical style after the early 19th-century earthquakes. Palazzo Trinci houses splendid frescoes from the early 15th century, some attributed to Gentile da Fabriano. In the hills near Foligno, the recently-restored Benedictine abbey of Sassovivo is worth a visit.

Foligno Memorable Moments:

  • In June and in September, the splendid Baroque festival la Quintana, transforms the city – and the people – who relive their 17th-century past with full passione.
  • All of Foligno is transformed into a great “tasting room” at the end of September when the celebration of Italy’s first courses, I Primi d’Italia, takes over the city. M create link to my article on blog
  • Towards the end of November, in the courtyard of Palazzo Trinci, the MieleinUmbria (“Honey in Umbria”) festival draws visitors who enjoying tasting varieties of honeys on cheeses, sweets and other Umbrian delicacies. Lectures on bee-keeping, concerts, plays round out the three-day festival
  • In late November, taste truffles and other Umbrian delicacies in Valtopina at the Mostra Mercato del Tartufo


Trevi (credits)

Between Foligno and Spoleto and in the midst of vast extenses of olive groves, Trevi seems to hang on the hillside overlooking the largest valley in Umbria, la Valle Umbra Nord. A quiet medieval town or pre-Roman origin, Trevi backstreets charm. The Museo di San Francesco houses Umbrian art of the past while the Flash Art Museum is home to a contemporary art collection.Trevi Memorable Moments:


Spoleto (credits)

The Roman amphitheater and Roman house bear witness to Spoleto’s ancient past, as does the cemetery church, built with remnants of Roman temples. A massive 14th-century Papal fortress dominates the town, flanked by a medieval acqueduct (walk across it!). The Renaissance lives on in Fra Lippo Lippi’s frescoes in the cathedral and my favorite trattoria there works magic with truffles.Spoleto Memorable Moments:

  • In late June/early July, il Festival dei Due Mondi draws lovers of music, art, theater, and dance from all over Italy – and indeed, all over the world

Valnerina/Nero River Valley


Between Trevi and Spoleto, just off the SS75, a highway cut-off leads through a tunnel into the Valnerina, where forested rocky cliffs rise in majesty above the Nera River. Scheggino, Preci, and Visso (in the Marches region) are charming Val Nerina medieval towns, each offering “hidden” secrets to the visitor. Sant’Anatolia di Narco, Ferentillo and San Pietro in Valle (11th-century frescoed abbey church) all entice. The Valnerina is not to be missed!


Norcia’s main square with statue of San Benedetto

The drive to Norcia, birthplace of St. Benedict in the 6tth-century, is quite simply mozzafiato (“cuts off your breath”) and when you’re there, treat yourself to tastings of Norcia’s prized prosciutto, pecorino cheeses and black trullfes at a famous norcineria. If you have time, take the windy road from Norcia to Castelluccio, not be missed for the flowerings end of in June, July.Norcia Memorable Moments:

  • Norcia celebrates the Feast of patron saint, St Benedict in late March with a variety of festivities.


Birthplace of 15th-century saint, Rita, Cascia, is tucked away in the mountains, not far from Norcia.

Cascia Memorable Moments:

  • Cascia is in full festive mode for the Festa di Santa Rita, May 22nd.
  • Cascia is also famous for its saffron, celebrated in a late October festival.


La Corsa dell’Anello (“Race to the Ring”) – Thanks to Ambra and Marco for the photo

Not many tourists in undiscovered Narni’s winding medieval backstreets. For me, the Narni cathedral, San Giovenale, is one of the most fascinating in Umbria (don’t get me started…!) and you just cannot stay in Umbria without seeing the Narni Underground, one of the most fascinating recent archeological discoveries in central Italy. And yes, I have a favorite restaurant here, too!Narni Memorable Moments:

  • During La Corsa dell’Anello in mid-May, the Narnesi once again iive their medieval history – and with what passione!


Not far from Narni, Amelia is most noted for its two-kilometer section of pre-Roman “cyclopic” city walls, made of massive blocks of cut stone. In the town archaeological museum, the town proudly displays a 1st-c. AD fine bronze statute of the emperor Germanicus, unearthed in the 1960’s during the construction of a mill. Wander the charming backstreets in this quiet Umbrian medieval town, as yet quite “undiscovered”.


Perugia (credits)

About twenty minutes west of Assisi, Perugia is most famous for its chocolates – and not only! Etruscan city gates and an Etruscan well, a stunning Papal fortress, splendid frescoed medieval guildhalls and a Gothic sculptural masterpiece, the main fountain, are just a few highlights. Take a few days to explore all the wonders.Perugia Memorable Moments:

  • In January, the city celebrates one of its patrons, San Costanzo.
  • In July, piazzas, palazzi, theaters, winding medieval streets come alive with the rhythyms of Umbria Jazz

Citta’ di Castello

Citta di Castello (credits)

Citta di Castello north of Perugia off the E45, is a less-visited Umbrian medieval town, famous for an international horse race in September and the white truffle festival in November.
The 14th-century belltower of the main square towers over the town. The 16th-c frescoed graffiti motif on the noble palace Palazzo Vitelli (housing the civic picture gallery) is unique to Umbria.Citta’ di Castello Memorable Moments:

  • The international horseshow, la Mostra dei Cavalli, draws visitors from all over the world in mid-September.
  • The truffle festival in early November is not to be missed.

Citta’ della Pieve

i Quadri viventi (credits)

Birthplace of Perugia, teacher of Raphael and one of Umbria’s most famous Renaissance painters, Citta’ della Pieve, northeast of Perugia, once was a fortified castle. The municipal buildings date from the 13th to the 16th century and the town’s main festival, il Palio dei Terzieri, brings to life once again the city’s past.
Cick here for photos of this town.Citta’ della Pieve Memorable Moments:

  • Il Palio dei Terzieri in mid-August is the town’s most splendid festival
  • The monumental crib scene in Palazzo della Corgna at Christmastime is not to be missed.
  • On Easter Sunday and Easter Monday, i Quadri Viventi (“living images”) bring to life the episodes of Christ’s Passion and death.


Gubbio: la Corsa dei Ceri

The panoramic road from Assisi to Gubbio is certainly one of the most scenic of Umbria. Time seems to have stood still in Gubbio, medieval gem, and tourism is limited as Gubbio is not a railroad line. A fine municipal museum, labyrinthine medieval backstreets, restaurants offering truffles and other Umbrian specialties all entice the visitor. A Roman amphitheater is testament to its ancient past and the funicular ride to the Basilica on top of the hill takes one floating over the terracotta rooftops.Gubbio Memorable Moments:

Gualdo Tadino

On the way back to Assisi from Gubbio, consider a stop in Gualdo Tadino, to visit the imposing fortress, la Rocca Flea.

Gualdo Memorable Moments:

  • At the end of September, Gualdo Tadino brings to life the 15th-century folklore in honor of St. Michael the Archangel with three days of festivites, high point being the pageantry in Renaissance dress – and the donkey races!

San Pellegrino

Small town near Gualdo Tadino, San Pellegrino comes alive the night of April 30th with a most amazing race.

Lake Trasimeno and area

Lake Trasimeno’s Isola Maggiore

About thirty minutes north of Perugia, Hannibal defeated the Roman armies on the shores of Lake Trasimeno. Charming towns surround the lake -Passignano, Magione, Castiglione del Lago, and Panicale, to name a few – and Isola Maggiore, the largest of Lake Trasimeno’s three islands, merits a visit, too.Lake Trasimeno Memorable Moments:

  • At the end of July, Il Palio delle Barche in Passignano del Lago brings to life once again an ancient rivalry between two noble families of Perugia – but in this festival, the rivals challenge each other in boats! Trasimeno Blues events animate all the lakeside towns from September to the end of November


Master maiolica artisan at work

For centuries, the maiolica artisans of Deruta (south of Perugia) have been creating intricately-designed ceramic masterpieces. A shrine outside the town astounds visitors wtih a fascinating display of hundreds of maiolica folk-art masterpieces dating from the mid-seventeenth century.


Todi merits a stop on the way to Orvieto. Enjoy a cafe’ or gelato or just people-watching while sitting at an outdoor cafe’ in the main piazza, facing the cathedral and surrounded by the crenellated medieval civic buildings. A couple of interesting churches deserve stops, as well.

Montecastello di Vibio

Not far from Todi, hilltown gem Montecastello di Vibio boasts a tiny gem of a theater, said to be “the smallest theater in the world”. Enjoy a walk through the meadnering backstreets, noting the urban layout, clearly indicating that this hilltown was once a fortified castle


Titignano, once a feudal castle, is a charming tiny village off the road between Todi and Orvieto. If you have time for a stop, do enjoy a lunch here of Umbrian specialties.



Evidences of Orvieto’s Etruscan origins live on in the tombs surrounding the town and in the fine Museo Faina just opposite the stunning black and white-striped cathedral. The Renaissance fresco masterpieces of Luca Signorelli are not the only treasures in the Duomo, as you’ll see….
Wander the winding backstreets and head into the medieval section of the town, too.Orvieto Memorable Moments:

  • Orvieto trumpets in the New Year with world-class jazz when the Umbria Jazz Winter festival takes over the town.


The castle-village of Bolsena

In northern Latium, Bolsena, lakeside town about twenty minutes west of Orvieto, remains a family holiday favorite. Lake Bolsena was once a volcanic crater and Romans settled along its shores. The medieval village boasts a fascinating church, charming spots to eat, and a prize-winning gelateria. On the western side of the lake, enjoy a buonissimo lunch near charming Gradoli.Bolsena Memorable Moments:

  • The stories of the martyrdom of Bolsena’s patron saint, Santa Cristina, animate the town in July.