On top of a hill facing Montepulciano, stands the medieval village of Montefollonico. It is far from busy roads and from the usual tourist trail–which is what makes Montefollonico so spectacular. Its isolation means that it is relatively unchanged from the 13th century. It is a fantastic medieval village, surrounded by 13th-century walls that still protect the hilltop village. With its narrow, winding streets and its low, rustic houses, Montefollonico provides a great view of Tuscany.
Montefollonico has a population of approx 150 people live inside the walls and about 600 people total live in all of Montefollonico ( if you include the people outside the walls). In addition to its views, it also has 2 great restaurants. One is known for its vast wine collection and the other for its view of Cortona. There is also a great cooking school there called Cook in Tuscany
Montefollonico has 3 active churches, but if you count all of its churches there are 7. The people are extremely friendly and love to welcome visitors. There is a grocery store, pharmacy, and a winery.
The one thing that makes it worth the visit is you will not find tourist shops or a street lined with vendors–you will only find a sleepy town that looks much the way it looked in the 13th century. Very little has changed–this is the charm of this lovely hilltop village.
2.5 hours north of Rome and off the tourist track. It is easily reached by car or train. I recommend traveling by car and parking just outside the walls at the middle gate and walking through the village.