Quandry about where to stay in Tuscany

There are hundreds and hundreds of area farms with rooms and apartments.
If you find a city or area outside a chosen city, pull it up on Google Maps. Then magnify the map and !little bed icons will pop up that you can click on. You will be guided to their direct websites, many of which have customer reviews.

David, you are not understanding what I am asking. I know how to search for places to stay. What I am asking is more strategic in nature - it has to do with deciding whether to break up the time and stay in two places versus one place in between the two, and specifically what that means in terms of the time I will spend traveling to my destinations versus the convenience of being in one place for five nights.

To meet your expectations of places you wish to visit, stay in Chianti region 3 N(Panzano, Radda, Siena) and then south of tnere in Pienza, 2N. I changed your allotment of nights as the places you list in northern area are farther apart.
Also, with teens, tey to find places to stay with a pool for the boys.

In the fall of 2015 my husband and I stayed three nights in Orvieto and three nights in Volterra, then we stayed two nights in an agriturismo outside of Orvieto before driving to a Rome airport hotel so we could take our morning flight back to US.

In that length of time we did not get to all the towns that we wanted to. It always takes longer than you think from town to town and with lunch breaks etc.
The towns we managed to get to were Montepulciano, Cortona, Todi, Chiusi,
(Chiusi not really worth it), San Gimignano, and Pisa. We had been to Florence, Siena and Assisi before.

The disadvatage of staying at an agriturismo is that you have to go into town for dinner if dinner is not available at the agriturismo.
In our case it meant going back after dark in an unfamiliar area. You could have a pool but you won't be there much to enjoy it. Staying in town lets you walk to dinner and stroll before or after. Also, the town will be much less crowded in the evening.

With only five nights, it's hard to say whether you should split them to two places. Maybe just stay north and get to as many places as you can from there. Save the rest for another trip.

The best part is there is no wrong answer. I would determine where you wish to visit, other than the the big cities and decide between one location or two.

There are literally hundreds of small towns, many no in a guide book that are wonderful to explore. The driving distances are shorter than you think.

I would personally stay in two locations so you can explore two towns in the evening.

I would make sure you have a GPS and not just a phone. Remember to get an international drivers license. I have been stopped in rural Italy by the local police who did not speak English. One look at the idl and we were on our way.

We have enjoyed driving in Tuscany and have explore great little towns, had great meals and found all the people friendly.

I have used Gemut.com to rent a car. It is a US company and they do all the work.

Have a great rip.

One other thought. Once you have identified your accommodation try and book directly. I have found the prices are similar and often you get a bonus. You also eliminate the fee the owners pays.

We have driven around Tuscany about 30 days in the past 9 years.

We try to go to the most distant location first and work our way back to home base. Rule is to travel no longer than 2 1/2 hours R/T.

Use rome2rio.com to get estimates.

Using a Siena agriturismo as your base, these trips are within that time constraint.

Siena-Volterra-San Gimignano-Monteriggioni-Siena. 65 miles 2 hrs.

Siena-Greve-Panzano-Radda-Siena.
77 miles 2H 20m.

Full day in Siena.
Edit: park in the Stadio lot to avoid ZTLs.

Siena-Pienza-Montalcino-Siena.
87 miles 2H 15m

Siena-Montepulciano-Orvieto
90 miles 2H 25m drop car. (Hertz only)
Spend the night in Orvieto and take an early afternoon train into Rome.

Based on what you want to visit, if you stay in the proximity of the Florence-Siena freeway, somewhere between Siena and Colle Val D’Elsa (near Monteriggioni for example), you can drive to all your destinations in less than 90 min, at the most.
If that is too long for you, and prefer drives under 45 min each time, then split your stay between Colle VE/Monteriggioni area and the Montepulciano/Pienza Area.
It’s up to you, how much you want to drive on a daily basis, and how much time you are willing to waste in accommodation changes, which takes a bit of time too for both bureaucratic steps and getting acquainted with the new environs.

Thanks for all the replies. After discussing with my wife, we have decided to split the visit and stay two nights in Siena or nearby, then three nights further south. Now I have to decide whether to stay in Siena itself, or look for a something in the countryside.

David,
We spent 6 nights in Siena this past April/May inside the wall. Our rental car was kept at a parking garage outside the wall and the garage staff drove us into Siena to our B and B each time we returned from the days outing.
I recommend you stay outside the wall of Siena if a- you will want to visit another area during your time there. And b- you will have a rental car at this time. You could find accommmodations outside the wall which would give you some flexibility in going into Siena or driving to another hill town. And don’t miss Pienza! We brought back a wheel of fantastic cheese and some truffle oil from there.

I always stay at Albergo Bernini when i Siena. Inside the walls. Love. love Siena. ONe of my favorite cities in Italy. Totally unique.

Siena is too large for me as a base with a car. We once visited lovely Casole d'Elsa, about half way between Siena and Volterra, and toyed with the idea of staying there one day. We were in contact with the following family, and they were very swift and pleasant with their responses.

https://www.poderemonti.net