Piero della Francesca's masterwork Madonna del Parto from 1467 is a must-see if you visit Monterchi, and following the trail of P.d.Francesca's works around the Arezzo region would be a perfect theme for an itinerary.
The work of the Madonna, proudly drawing attention to her visual pregnancy, was discovered in a chapel in Monterchi, but is now displayed in it's own building, a former school house. It was restored in 1992/93.
What made our stay in Monterchi even more perfect, was the welcoming smile of the local shop-keeper, every day when we visited the local store.
What to buy: The lievito I bought here (thanks for understanding my halting Italian!) made me make the best pizza I ever made when we came back to our rented country house.