Community Feel in Tuscany

Last fall we stayed outside of Cortona in a farmhouse we rented, we spent most evenings in Cortona having dinner, sitting at a cafe drinking a glass of wine and people watching. I think you'd really enjoy it. Since we had a week, we also wanted to use as a home base to day trip, so our days looked like this. 1) Day in Cortona 2) Train to Florence for a Soccer match 3) Cooking class (Cortona) Alesandra's Home Cooking Class 4) Siena (about 45 minutes and easy drive to/from) 5) Train to Florence to sightsee for the day 6) Montelpulciano (about 30 minutes, easy country drive with no traffic) We loved this town, partly since we are into wine.
7) Last day drove from Cortona up through the Chianti region, stopped at a winery for tasting, tour, and lunch, and ended up at the airport around 4:00. We could have squeezed in much more if we went morning to night, but we enjoyed spending late afternoons at the pool overlooking the valley, relaxing with a bottle of wine. You may want to check into renting a car in Orvieto, then returning it in Arezzo (about 30 miles from Cortona), then take the train to Florence.

You should consider posting this request on SlowTravel Forum as well. I bet you get some good responses.

I think you should narrow down which places you might want to visit for your day trips before deciding on a base town. Then you can pick a base town that's the most centrally located to where you want to go during the day. In terms of the feel of a community, any of the towns you mentioned will have that feel - Cortona, Siena, San Gimignano, Montalcino, Montepulciano, etc. Cortona is on a higher hill than most of the others, if that's a factor. It's also on the eastern edge of Tuscany, and for that reason may be less centrally-located to other towns in Tuscany (though Cortona is convenient to several lovely towns in Umbria). In our experience, our travel times from Cortona to other places were longer than the other poster's. And if you're staying at your home base for 5 days, you'll be doing a lot of driving to and from. If you're interested in wines, then consider a place a little more south and west, such as Montalcino. On getting to the Cinque Terre, I think most people would advise that you drop off your rental car somewhere and take the train. We've driven to and from the Cinque Terre several times with no problem; especially if you already have the rental car, it's a bit more time-efficient. Monterosso has a public lot, and some of the hotels have parking as well.

We stayed three nights in Chiusi last year and it was a good base for day trips (would have been even better with a car) as we relied on the train which stops at the base of this very small hilltown. There was definitely a community feel although as is typical in Italy, people are polite but don't exactly want to be your friend. There are only a handful of hotels and restaurants, but I had the best pasta ever there. What is nice about Chiusi is that it is very quiet! This town shuts down early and you can leave your windows open at night. It is also centrally located for visiting both Tuscany and Umbria.