Montefalco is a hilltop town made famous as a wine producing center. It also boasts medieval architecture and frescos dating back to the 1400s. Read also: https://www.cntraveler.com/stories/2015-03-09/why-montefalco-is-italy-best-new-wine-region
Several villages dot the shores of Lago Trasimeno. You can rent a boat from a number of locations, go for a swim, or visit the Museum of Lake Fishing in San Feliciano. There are a number of shoreline restaurants in San Feliciano to take in the views as well. We once promised Ross we would take him out in a wood boat here, but we didn't fit it into our trip. See also: https://www.lagotrasimeno.co.uk/
Bevagna is another picturesque medieval town located not far from Monticelli. There are a number of restaurants and shops along its pedestrian streets. You will need to park outside of the city gates and walk into the village on foot.
One of the most famous places in Umbria, the basilica is a UNESCO world heritage site. Simone di Pucciarello donated the land for the church, a hill at the west side of Assisi, known as "Hill of Hell" (Italian: Colle d'Inferno) where previously criminals were put to death. Today, in a true 360, this hill is called "Hill of Paradise".
This is a small cafe in Bevagna that has some connection to anarchy and a great beer selection. The food is excellent!
Closest restaurant to the castle for a quick meal.
Perugia is the largest town in proximity to the castle -- about 160,000 inhabitants live within its boundaries. The town offers boutiques, museums, bars and restaurants. The New York Times called it "one of the country’s most vibrant and underrated destinations." We highly recommend you spend a day here!
Spina is a small town located ~10min drive from the castle where there are a few restaurants for a quick bite.
The world's first carbon neutral vineyard! Take a wine tour.
Organic and biodynamic wines on a beautiful farm.