Certaldo Alto is small and can be seen in its entirety in a couple of hours giving you lots of time to wander, eat, and shop.

Cortana is one of those quintessential Tuscan towns built into a hillside with mesmerizing views of the Valdichiana below.

Cortona is small enough that you can wander the streets and alleyways to find a quaint little restaurant that meets your appetite. Here's 2.

Vicopisano's prime geographical location made it rich, but a diverted river turned this Tuscan hilltown into a sleepy town.