Check the festival and market schedule as you may want to adjust your days accordingly.
Day 1: Arrive from Rome in the morning. Rent a car and head toward Casa Grifone. On the way, if needed, stop for coffee at an Autogrill. If you make it to Todi between 1pm and 3pm, stop at Trattoria Piero e Silvana. As you leave Todi toward Casa Grifone, stop at the EMI store to load up on wine, water, and food. Grab an assortment of antipasti (bread, cheese, pate, various salami, olives, etc.) to eat for dinner. Arrive at Casa Grifone and try to stay awake as long as possible.
Day 2: Since you’ve just had a long journey, let’s pick something nearby to explore. Todi (lunch at Pizzeria Cavour) and Monte Castello di Vibio. Make reservations for dinner at Il Grottino di Zio Toto or Osteria Novecento.
Day 3: Visit Assisi and stay there for lunch. After a long day and likely a late lunch, relax at home or walk up to La Torracia for cocktails and a pizza.
Day 4: Visit Orvieto and stay for lunch. If you want to see more, drive a little further and see Civita di Bagnoregio or visit a winery. Relax at home for dinner or go to Diamond Cafe in the small cluster just below Monte Castello.
Day 5: If you are into wine, head toward Montefalco. If you are into Roman history, head to Bevagna. If you want instagram influencer worthy photos, go to Spello. All three towns are close together so it is possible to see them all in one day but it is likely you will only have time for two out of the three. Each have great restaurants. If you want to visit the wineries, be sure to make an appointment. It is also possible to taste wines at some shops in Montefalco.
Day 6: Perugia – go early and stay for lunch or late in the afternoon and stay for dinner.
Day 7: Visit a unique church then lunch at our favorite place and a look around Marsciano or if you are interested in pottery, go shopping in Deruta.
Other day trips if you have longer:
Norcia and the Piana di Castellucio
Gubbio
Sirolo and Numana at the beach
Lago Trasimeno and surrounding towns
Arezzo
Spoleto