Last summer I went to Italy for the month of August. That sounds super fancy, I know, but I do not have the funds to be considered fancy by any stretch of the imagination, so please withhold your judgement and snark for the time being. Though I do really love the snark. I was able to go because Bossy cashed in her airline miles to get me a gratis ticket (which was insanely generous) and we had a free house to stay in Panicale in Umbria.
Panicale is ideally located right next to the Tuscan border, so driving around from cute little countryside village to walled gothic town was really easy (well, for the most part considering I did get car sick for the entirety of the month, which was less about Italian roads and more about the driver of the rented Cinquecento but whatever).
The first day trip we took was to Montepulciano (where my beautiful copper stock pot was forged), and it was one of my favorite places in the whole of Tuscany because of the breezy, beautiful walled in spot on the top of a hill overlooking the region. It was a gorgeous day and we were lucky enough to have access to the best wines of the region in the numerous bars that dotted the peak of the city.