Does anyone have advice on whether we should rent a car to travel around Tuscany (from Siena hotel as a basepoint) or do organized bus tours? This is in early October, 2016 for 3 days. My hotel does have parking for a fee.
A car is good to have to visit the small towns in Tuscany. I'd rent one and in fact I always do, every year.
I'd rent a car; an organized bus tour is okay if you like such tours; doing it by public bus is not a good idea.
I travel by public transportation when I am alone, plenty of hill towns are accessible by train and/or bus. But, I travel pretty slowly when I am going solo.
If you plan to visit three a day, rent a car. It's great to see a little town on a hill and decide to go there. If you don't want to rent a car, you just have to be more organized.
2 years ago we rented a car for the first time in Italy and it was easy. It was September and October. There were two of us so navigating was easier than perhaps a single but definitely doable. We are in our mid 60s and do have experience with a stick shift.
Rent a car, take a camera, and enjoy the countryside as well as the hill towns.