Italy has hill-top towns everywhere. Most are medieval in origin. The Umbria region is no exception. Travel, wrote a BLOG on hill-top towns to visit when you are in Umbria. Montefalco is one of my favorite cities. It is old but looks artistic in design. You can plan trips from a central location and see many of these great hill-top cities. Rent a car and drive through the country side and visit as many as you can. You will feel you have been taken back in time to an earlier time in human existence. Enjoy it, eat the local food, drink the local wine and speak with the local people. This is how to experience the real Italy.
George & Jo Anne