Tuscan Day Trip, please advise


New member
I did post a similar question earlier, but I'm still having trouble and I hope someone can help.
I am planning a day trip (with car-driver) starting in Florence and ending In Siena. So, we want to see towns on the way (and further south of Siena in Val d'Orcia). I'm just not sure which towns (or wineries to choose). I was thinking of Montepulciano, Pienza. But, I've read that even if you get to the center of town by car or mini bus, that it is very steep everywhere. My mom can't handle that. So, now I'm trying to decide which twons to choose. Maybe Greve? I think Pienza is still a good choice. I assume we'll stay in each town for maybe an hour and that we'll stop in probably 3 towns total (?).
Maybe Montalcino is a good option.
My mom mostly wants to see the beautiful Tuscan countryside, and I'm the one wanting to stop at a winery. To have lunch at a winery overlooking the country would be great.

Thanks for any and all advice!