Drive to Cortona and Assisi

At least 6 hours of your day trip will be spent driving and parking. Europe switches back to daylight time on the last Sunday of October, therefore it’s dark shortly after 6pm. Statistically, the first week of November is the raniest of the year, so there is also a chance your drive will be slowed by weather conditions.

Moral of the story you can devote only a couple hours to each place. Doable but very rushed.

Roberto beat me to it. It would indeed be a very long day if you tried to visit both places on the same day.
Might suggest selecting one or the other and concentrating on that. As he pointed out you'll be dealing with short days and the increased possibility of rainy weather that time of year. The driving will be slow too ... at least that portion in the hills of Chianti - normally a pleasant meander on a sunny day but frustratingly slow if you're trying to get from point A to point B in a timely fashion.
Pick a day when the forecast calls for fair weather and then get an early start to avoid having to tackle the roads after dark on your return that evening.

Thank you Roberto . . . your advice is always so helpful!!

And thank you, Robert!

Both are possible; of course Cortona is much closer than Assisi. Trying to do both in a single day would be too much.

Thanks all! I'm beginning to think of the reality of it all. Sadly, maybe I will just consider Cortona.