Hill Country without a car

I think you could make your plan work much better if you stay in the town instead of just outside the town.
A town like Montepulciano is so small and concentrated it is in no way a city feel and staying right in the middle of the town gives you the real Italy town feel you won't get at some farm in the country (anything outside of town is a farm in the country basically).

Not only does this make public transit via busses a possibility but it also puts restaurants, shops, etc.. .within easy walking distance.

Even in town I think you may struggle with public transit as the bus schedules are more geared toward local workers and students rather than tourists.
There may be tour operators that pick you up from in town or out of town locations, others may know.

Have you checked with the accommodations?
It is really not a big deal to drive in rural Italy--I detest driving, as does my husband (we bike to work at home), and once we branched away from places that are on the train lines, we have had three successful driving trips. I think it is really that or stay in a town instead.

Bus schedules are often reduced or nonexistent on Sundays and I see no Sunday bus to cover the 10 km between the hilltown and its namesake train station (nor the longer ride to Chuisi), so you'd need a taxi to make that connection.

We also prefer trains and or buses. Last Fall we stayed in Volterra for three nights and it was wonderful! Staying in town enabled us to walk to restaurants and sites. We loved getting to know the town and saw several of the same locals each day. Getting there from Lucca took two buses but was doable. We left Volterra for Florence and rode a bus to Pontedera and then an easy train ride to Florence. We did get to ride with several school children but that was half the fun and local experience. We wanted to visit more hill towns so opted for a small day tour from Florence with tours by Roberto. It was great and allowed us to experience places we could not have seen without a car. You can see more with a car but we prefer to stay in one place and get to know it rather than jumping around everyday. Have fun!

I think you'll find that tours depart only from the larger cities like Florence and possibly Siena. You can check by Googling "Tours from X"; the information is probably also on TripAdvisor.

I think it may be difficult if not impossible to get from the town of Montepulciano (much less from your lodgings outside town) to either of those cities early enough to catch a tour. I sympathize, because I am totally dependent on public transportation myself. I think if you want to see much of the countryside you'll probably need either to rent a car (which would certainly be my choice if I could handle a manual transmission and was in a party of 2 or more) or split your time between Florence and Montepulciano. Whether it's at all practical to stay in the rural accommodation you have selected vs. the town itself will depend on the local bus schedule, which I haven't investigated.

I've never tried to stay in a rural area. I have not been happy with the location of some of my city hotels, because they were near the train station (the reason I chose them) but in a restaurant desert. I've found it beyond annoying at the end of the day to have nowhere to eat within 1/2 mile or so of my hotel. (I am far too penny-pinching and stubborn to use taxis.) The prospect of being isolated in the countryside (however beautiful the lodgings) makes me twitchy.

All of you have been really helpful and have told me what I suspected was true. We will go back to the drawing board, taking this all into consideration. Better to know it now. I’ve enjoyed hearing from you! Ciao!

I went from Montepulciano bus station to Chiusi train station on a Sunday and recall that there were a reasonable number of departures available. My trip was either May or September, don't recall which. The owners of Meuble il Riccio hotel in Montepulciano used to offer custom designed tours in vintage Italian cars. Not certain whether they still do, but 2 woman staying there while I was visiting took such a tour and said it was excellent. My guess is that they could pick you up at your location just outside of town. You might find information on the hotel's website or by e-mailing them.