We are leaving in next week for a month in Italy. The first 8 days are in small town in the hills about half way between Pisa and Florence.
I have used guides, Google and Rome2Rio to put together some day trips. However, I don't want to spend the whole day driving. We plan to do a loop routes. We have a good car and GPS and have driven in Europe before. From there we go on to Florence, Venice and Rome so we don't have to go into Florence.
We are Looking for ideas along the way and maybe what percentage of our day to spend in one place over another. We have been to Europe and Italy before but we have aged a bit and don't want to overdo it...Except with food and wine!
Thanks for any input to make our trip fantastic!

Trip # 1 San Gimigiano and Volterra
Trip # 2 Siena--all day
Trip # 3 Moltepulciana and Pienza
Trip # 4 Pistoia (on Saturday market day) Santurnana ( quick look around as our grandfather was born here. ) Lucca Pisa (could turn this into a second day)
Trip # 5 Greve and Chianti--I haven't done research for this area as yet so help!!
The other days we are taking cooking classes. That Still leaves us with a day open so we can be a bit more flexible.
Thanks

we recently spent a few weeks in a small town in the hills about half way between Pisa and Florence.

my 2c.
San Gimi and Volterra, easy to do in the same day, or 1/2 day to each.
Siena, easy.
Montepulciano and Pienza - too far
Pistoia - long way away
Greve / Chianti - easy

There are market days in every town, no need to drive a long way to get to one. I reco you avoid market day (Wed) in Siena. Getting parking is a problem and most of the goods sold are cheap imported clothes and housewares for local consumers.
Consider just exploring near your small town - there are lots of walking paths you can take, including a long stretch of the pilgrim's walk, or hiking along the river/in the woods, or finding local markets, etc. If you run yourselves ragged before you even get into the big cities where that will happen anyway your trip will be a blur.

Thanks for the good info. We are going to Pistoia only because it is on the way to where my grandfather was born. Now I know to avoid the big town markets. When we lived in Germany we always stopped at markets. Sadly I also have noticed that the traditional hand crafted items are being replaced by cheap imports. I wonder if we are going to the same place you stayed? Is the letter "H" prominent in the title?

Where exactly are you staying?

Whether any particular destination is too far depends first on how much time you really want to be in the car and whether you're comfortable driving back to your small hill town in the dark. I personally set a one-way limit at about an hour, wouldn't visit two towns in one day unless they are very close together, and avoid driving in the dark if at all possible.

By my parameters, most of your day trips wouldn't work for me.

San Gimignano is probably more than an hour from your small hill town. (I'm going to pick Staffoli as a stand-in.) Since you have to park outside of towns and walk in/out, it would take an hour or more to get from the center of SanG to the center of Volterra. Driving back to your small hill town would take another 60+ minutes. That day: probably 3.5 hours of driving.

At probably 90+ minutes each way, the drive to Siena would make for a long day. Too long for me but perhaps not for you.

Montepulciano/Pienza would be close to 5 hours for the day, even driving the boring autostrada rather than the more interesting secondary roads.

Trip #4 would work for me. I'd probably have time for Lucca but definitely not for Pisa.

Trip #5 would probably work for me, but I like the smaller towns more than Greve. So, Radda, Castellina, Panzano instead... I second the suggestion of driving SR222 as much as possible.

sorry - my mistake. I misread your location (betw Pisa and Florence) as between Siena and Florence. We stayed in Colle di Val d'Elsa

My reo still stands though - focus on place closer to where you are staying, and don't drive far away (eg montepulciano) just to check off another tuscan hill town. You'd be far better off slowing down a bit and just enjoying where are you are. Driving through the countryside is not a relaxing/stress free drive. Narrow winding roads, need to be on constant vigil for trucks/buses coming the other way, bikes in your lane, non-existent shoulders, guardrails and or walls within inches of your car, other drivers (either italian or foreign) on your tail, slow drivers in front of you that you want to but can't pass, etc, etc.

First visit to Tuscany back in 2000 we stayed in the tiny village of San Sano about 20 min drive north of Siena. One day we did a lovely lunch at La Badia di Coultibuono. If they still get good reviews, I would recommend it! The is the family home of Lorenza di Medici. We got to do a tour of their wine cellars and gardens too. Lovely and interesting. Their Chianti Reserva was excellent.

PS - La Badia di Coultibuono is near Castellina.

I just googled to update myself so correction: It's Badia di Coltibuono and it's near Gaolie.

Badia di Coltibuono near Gaiole in Chianti.

Thank you all for the great info. I am sure all of your input will improve our trip. We are comfortable driving in Europe--even on narrow hills. However, we will cut back driving and relax at the house with a bit of vino! It is my sister's first trip to Europe so we are pushing a bit. From Tuscany we get on the train and we have apts in Florence, Venice and Rome. It will be super.