Montepulciano

You'll get more replies if you post on "Italy" rather than "Italy reviews." The latter is meant for people to report on places they have been. Montepulciano does have little shuttle buses that take you "up the hill." But it's true that there aren't a lot of areas that are flat.

Steep and lots of walking is true for all "hillside" towns.

Month of year? You might consider Orvieto by train. Public transportation is not ideal for multiple Tuscan hill towns. I don't even like renting a car, but it works well in Tuscany. Usual warnings on IDP, ZTL, insurances, visible luggage while parked.

I love Florence, but don't consider it an ideal base for Tuscany. Even with a car. It does however, support an infrastructure of daytrips and tours, if you are not a low-budget traveler.

Montepulciano is basically one long hill, steeper in some places than others and does involve a lot of walking. It sounds like perhaps you should explore other options. As Bob points out, all the hill towns are hilly.

Your details sound like this would not be a good choice. The small orange shuttle will take you up the steep hill, but the only flat part of Montepulciano is the piazza at the top, and it’s fairly small. Nearby Pienza is much flatter.

Some parts of Siena are much less hilly. I would recommend taking the bus which will leave you off at a flatter area, and it’s near the Campo.

Another great option would be Lucca. It’s flat and a nice Tuscan town. It’s an easy day trip on the train.

Ferrara isn’t in Tuscany (in the Emilia-Romagna region), but it’s just an hour by train from Florence and is also flat. There’s a castle in the center of the town and also some interesting museums.

Ravenna is very flat and is two hours by train from Florence. It has the gorgeous mosaics in several churches and an overall a nice city to visit.

We stayed in Florence over a long weekend before renting a car and heading south an hour into the Tuscan hills. Virtually every farm in Tuscany has apartments and rooms for rent as a secondary source of income.

We stayed in an agriturismo between Certaldo and San Gimignano for 4 days..

We found the Tuscan roads to be well paved but a little crooked. They were well marked and not heavily traveled. No problem at all driving from hilltown to hilltown.

We turned the rental car in at Hertz in Orvieto--across the street from the train station. And the ride into Rome Termiini was only 70 minutes.