I am planning our first ever trip to Italy and want to spend about 5 days (out of nine) in Tuscany. I am looking at dates between Sept 16-Oct 6. Although there can never be guarantees, what is the weather like then, generally? Is Sept very hot or October typically chilly? Any other advantage or disadvantage to choosing one week over another within that range?
My game plan is to spend 2 days in Florence, one in a smaller Chianti town (Greve?) and two in Siena. I'd like to rent an apartment, not so much because I would cook at home but just for the slightly more authentic feel of living in a neighborhood among locals. I know one generally cannot do that for two days at a time, so I am thinking B&B's as being the next best thing. Any comments?