Plunge Into History in Some of the Most Picturesque Towns in Umbria

After breakfast at the hotel, start the day by driving to Assisi at 09:00. The town is walkable, so it is recommended to leave the car outside the city walls. I suggest you leave the car at Parcheggio Saba Matteotti and walk the 10 minutes to Rocca Maggiore.
This is one of the most prominent landmarks in Assisi and a must-visit. The medieval castle boasts sweeping views of the picturesque town below.
Dating back to 1173, the fortified structure was torn down a few years later and rebuilt by Albornoz in the mid-1300s. Today, you can walk through the different rooms in the castle to get a feel of what it would be like back in medieval times. Take a guided tour to learn more about the intriguing history this castle hides.
Opening hours: March and October: 10:00-17:30 April, May, and September: 10:00-19:00 June, July, and August: 09:00-20:00 November to February: 10:00-16:30

The catholic church of Santa Maria Sopra Minerva in Assisi is hidden behind what appears to be a perfectly preserved Roman Temple. The six columns guarding the entrance resemble a pantheon but once you step inside, you Baroque style chapel adorned with gold and frescos.
The temple was originally named after Minerva due to a female statue that was found inside, but later it was found a stone dedicated to Hercules there.
Entry is free.

Dedicated to San Rufino, an archbishop of Amizah in Turkey from the 3rd century, the Cathedral of San Rufino is one of the few sites in Assisi which is not dedicated to St. Francis, even though the saint is said to be baptized in the basilica.
Legend says that Rufino was thrown in the river with a stone around his neck for speaking his religion. Supposedly, 7 citizens pulled out his body, fought the 60 men of Bishop Ugone, and won. The victory was seen as a miracle and the bishop ordered the renovation of the basilica.
Other than visiting the chapel, you should climb the steps to the top of the clock tower to marvel at the terracotta rooftops covering the town.

Assisi's most visited basilica and UNESCO World Heritage Site, dedicated to one of Italy's most important patron saints, Saint Francis, can not be overlooked when visiting the picturesque town. It is actually made out of two churches an upper and a lower church and the views of Assisi are impreccable.
Saint Francis pointed out this spot for his remains before he died and the building started with his death in the year 1228.
Among other implausible artwork, you will witness one of the finest in Italy - the total of 28 frescos depicting Saint Francis' life painted by Giotto and Simone Martini.
The entry is free.

Indulge in a flavorful lunch at Trattoria da Erminio, a traditional Umbrian restaurant taking you back in time with a cozy atmosphere. Especially the vegetable soup and bruschetta are amazing!
Opening hours for lunch: Friday-Wednesday: 12:00-14:00 Note that it is closed on Thursdays! A good alternative if you happen to be there on a Thursday is to try the risotto at La Piazzetta delle Erbe. Opening hours for lunch are Tuesday-Sunday 12:30-14:30 and Closed on Mondays. Check out their website here

Before entering Orvieto, head to the Belvedere di Orvieto where you will get spectacular views of the hilltop town. There is a restaurant at the viewpoint, but they usually open later in the evening.

Drive to Orvieto and check into your hotel. Affittacamere La Piazzetta is situated in the heart of the historic center but they have private parking that you can use.
The Bed and Breakfast is a short walk from Orvieto's top attractions like the cathedral and Orvieto Underground.
I recommend calling Orvieto Underground to make an appointment for a tour for the next day at 12:15 to secure your spot. If they for any reason can not take you on the 12:15 tour, you will need to shuffle the day around to accommodate it.
In the months of November to February, most attractions in Orvieto close early (between 16:00 and 17:00,) which is why the evening will go to walk around the open air sites in Orvieto to avoid meeting closed doors if you travel in winter.

Take a walk through the enchanting medieval streets to the Piazza del Popolo. On this square, you will find Palazzo Del Capitano del Popolo, an epic medieval building that I have always found closed to the public, but it is nice to see from the outside. You can walk up the stairs to get a nice view of the square.
This used to be a meeting point for the people and a seat of power. Today, it is used as a conference hall.

Continue your evening stroll past Torre del Moro to Piazza della Repubblica, another beautiful square where you can marvel at the Sant'Andrea Church and its unique 8-sided tower.
Back in the days, before the Duomo (Orvieto Cathedral) was built, this church was the religious center of Orvieto.
It is also believed that Piazza della Repubblica used to be the site of the Roman Forum in the Roman era.
Take your time walking around the quaint streets before heading to the restaurant as it does not open until 19:30.

Head for a fantastic dining experience at Trattoria la Palomba. Especially the pasta dishes are fabulous and the local wine tops the experience in this rustic place.
Opening hours for dinner: Thursday-Tuesday 19:30-22:00.
Note! It is closed on Wednesdays. A great alternative that is open 19:30-22:30 Wednesday-Monday is Trattoria del Moro Aronne. Check out their website here

Feel free to wander the streets to soak in the warm light of the street lamps covering the medieval town and stop for a last drink before heading back to the hotel. Orvieto truly turns magical after dark!
However, be ready for an early morning tomorrow, so don't underestimate a good night's sleep.