We are traveling mid-October to early November Rome to Umbria/Tuscany/CT/Venice and Florence. I'm wondering what to expect for weather at that time and whether I'm looking at summer or fall/winter clothes to pack. Any advice?
First of all, check weather.com several weeks before going to see the trend. Once I was there in October and November, and it was quite cold for that time of year. I was in a jacket often, using the umbrella often. The next time I was there during those two months October was absolutely hot and November was moderate. You are at the mercy of Mother Nature. Take dark colors for fall, but plan layers so you will be prepared for hot or cold.
We travelled to Rome and Venice in mid October last year and the weather was cool. It was much cooler in Venice than Rome. It also rained in Venice while we were there.
I second CS. We had 3 warm sunny days in Rome, then a front went through and the temp dropped to record lows with a stiff wind. In the hill towns it was sunny but the wind brutally cold. I suggest taking some form of hat or headgear. You can usually buy a coat or jacket (albeit at a steep price) but hat or headgear seems hard to come by on short notice.