Tuscany late September v. Mid November

The fiance and I are trying to plan a trip to Italy, most likely Tuscany, for our big honeymoon trip (note, we're not going right after the wedding and will be taking a "mini-moon" instead, so this will be more of a "regular" trip as opposed to the lounge around and do nothing honeymoon trip).

We are thinking 10 days (Thursday - Sunday) with flights in and out of Rome. The tentative itinerary would be 2 nights Florence (train from Rome), four nights Montepulciano (or another similar town), 2 nights Siena, 1 night Rome - fly out.

we're weighing going in either mid to late September or the second week of November. The flights in November are better/cheaper, and it would be low season thus (hopefully) allowing us to avoid hordes of tourists. We're a bit concerned about the weather, less about the cold and more so about rain. On the flip side, late September would allow us to enjoy better weather (eating outside, more enjoyable trips to small towns, etc.), but things may still be a bit crowded.

Does anyone have any experience that might tip the scales either way? If we go the September route, we could possibly head south to Amalfi instead of Tuscany, but I worry its still going to be pretty crowded.

If its helpful, when we travel we like to eat, drink, and look at beautiful/cool things and scenery.

Thanks in advance for any suggestions!