Where to go in Tuscany

Orvieto makes a good first or last stop to/from Rome
( Umbria not Tuscany)
There is a Hertz dealer there although AutoEurope no longer books with that location
Chiusi has Avis and Europcar

Since you’re going to Florence renting a car as you leave there makes sense
We are returning to the Val d’Orcia - Montepulciano, Pienza, San Quirico etc since we loved it so much first visit

Might head to Florence on arrival get car then to Siena and continue on to spend a few nights at agriturismo near Montepulciano
Then Orvieto - either drop the car there or drop in Rome

Although that might actually be too many locations in just 8 days

Sounds like Orvieto might be a good starting place for you. Easy train ride from Rome, wineries galore, not stayed at an agritourismo but there are lots in Tuscany.

We did the train from Rome to Orvieto, rented a car & stayed at Anticaolivaia agriturisimo. LOVED it! Fabulous hosts, delicious food & we had the ability to see much more with the car. We loved Orvieto so much that we’re planning to go back 2 more times.

We drove to Siena & stayed at another agriturisimo, which was fabulous. I’ll check for the name. We loved Siena & the car also gave us the ability for day trips in the hill towns. Easy drives. We dropped the car on the last day & took the bus back to Rome. All recommendations on these sites say not to drive in Florence or Rome due to the zone fees.

Absolutely do not drive in Florence or Rome but getting a car as you leave the city is fine

You can take a train from Rome’s Fiumincino Airport to the Roma Termini station and change trains to continue on to Firenze (Florence) S. M. Novella station. The total time takes 2h 30.
I would then take a direct bus to Siena (1h 15m) and sleep there for two nights. On day two take a direct train to Montepulciano (1h 15m). You’ll need to take a taxi from the train station to get to the city center.
Rent a car before departing Siena and get on the Crests Road but do not get an early start because you want to allow time for the clouds to lift to appreciate the rolling hills and well-maintained farm houses; this is the Tuscan countryside.
Since you’re wine lovers you may want to sleep in Montalcino (1h 15m) or somewhere close by for two nights. Not that there’s much to see or do in the town, but it’ll make a decent base to visit Pienza’s old town the next day (30-minutes).
The next day I would drive to Orvieto and drop off the car and sleep there (1h 45m) one night. The next day you can take a train to Rome’s airport (2h 15m).

Thank you all so far for the amazing suggestions.. will digest- map it out - may come back with more questions..

If you go to Florence, take a food tour. I think the one we did was Walks of Italy.

Look at the Chianti region between Siena and Florence for your stay. We have spent time in several of these charming towns, Castellina, Radda and Panzano.

This is a food/wine/culture trip… maybe a farm stay —don’t need a pool -just some amazing cured meats, cheese and wine… did I mention wine!!!

We stayed at Castello di Verrazzano just outside Greve and had a wonderful time. It is near wonderful villages and an easy bus ride to Florence.

We made a day of taking advantage of their winery tour followed by a fantastic food and wine tasting. I suggest you fast the day before and not plan on dinner that night. By staying at the winery, you won't have to drive after sampling.

We also had dinner there one night. It was just before Christmas and we were the only guests staying there. Two local businesses were having their Christmas dinner celebration that night. One was a tour bus company and all their drivers were there. They were a fun bunch and we ended up joining their party, much to both our and their delight.

In addition to our day trip to Florence, we did a day trip to Siena. We also did a day trip to San Gimignano and Volterra. Other days we visited small towns like Castellina and Radda. We also visited the Abbey of Monte Oliveto Maggiore, visiting the Abbey that day, then attending a gorgeous Vesper service that night where we and one lady from a nearby village were the only attendees beside the monks, who celebrated with Gregorian chant. They invited us to join in the responses.

Once again -thanks for the information. There are so many towns, farms, wineries - it is so helpful to get firsthand advice. Will report back with a possible itinerary soon.