Tuscany towns recommendations for 3 day trip

I am always torn between changing bases and longer car rides, but even for someone like me who hates being in the car, the hour drive between Siena to Montepulciano puts in a "consider one base" category. You don't get the different flavor in evening, but you don't have to unpack--so there is really no one answer!

RE day trips in between stays: Be sure to not leave anything in the car you could not live without, as trunk theft is a possibility (don't let it ruin your trip; just be aware).

I believe there is a train direct to Salerno, whether it stops in Naples or not.

hey hey PE
your 4 days tuscany (siena 2 & montepulciano 2) is cutting it short roaming around. check-in times for hotels is usually 2-4pm and check out 10am-11am) giving your family an evening & a day then what it takes to get ready for check-out next morning.
do you have parking at hotel or how near in siena and montepulciano? so much moving around and time spent driving to different towns with finding parking takes time plus safety with luggage left in car
make sure all drivers have an IDP from aaa.com/IDP which is mandatory for italy before flying to italy. have a fabulous vacation
aloha

While I'm not averse to driving, and the distances aren't great, Volterra and San Gimignano are in the opposite direction from Siena as Montepulciano. It might make more sense to have a hotel with parking in Siena and do those 2 towns as a day trip. Then move to Montepulciano the next day. That way there's no back tracking, and you dont risk leaving all your luggage in a parked car while you sightsee.

From Chiusi, there appear to be quite a few trains that would get you to Salerno, according to Trenitalia. Some are only one change. There are different connecting stations depending on time of day.

Thank you all for your valuable inputs and recommendations. I will explore to see if there is a possibility to keep Siena as my base for all 4 nights and do the day trips to other towns.Thanks!