We're a family of 4 (we're mid

"… so not too rural …. but we're after a real Tuscan experience and dont want to live in a city/large town"Very difficult without knowing a little more about how big a place you want? I note your location is Siena, which many see as on the large side, but I see it as small compared to say Milano. Both places we loved by the way.

Very good point, but we dont know the area well so just starting to research options in more detail. I'm from London so Siena is small for me, but we're looking for somewhere smaller than Siena (farmhouse/a fair amount of land and pool) but also ideally with some nightlife (restaurants/bars). 

6 month, what time of year – summer? I guess for 6 month getting to and from an airport is not important. How about things you want to do there – visit towns/cities? Classic Tuscany to me is anywhere between Certaldo and Montepulciano with “Chianti(shire)” right in the middle. A lovely place, but not one I would want to live in, and indeed we preferred northern Tuscany. Not ridged but I would say anything under 5,000 population and you will be lucky to find a single bar and a restaurant, but there are of course exceptions. I would look at places like Greve, see if that’s too rural/small and update here and perhaps others will chip in with suggestions. Use google street view to tour around a few places, can pan around to see the place nicely. Also you can use something like this website to get an idea of the size of the place and a search on the main town in the area will give you lots of information about it and the surrounding area. A search for the town name along with “restaurants” will tell you how well served the place is… 

Thank you this is very useful.  March - Sept - airport nearby not essential but good for visitors! 

Not too small. Not too big. Someone suggested Greve which is very nice. I might add...1) make sure you are in a town within a few clicks (walkable) of a train station; or often-served bus line.2) find a town with basic services like a butcher, hardware store, farmacia, maybe even a small super.3) find a town that hosts a weekly market4) consider areas other than Tuscany. Umbria and Le Marche  also have much to offer.5) be close to a rental car office for those times when you want a car6) make sure thetown has at least one BancoMatWe lived several months in a small town on the Adriatic coast that most would consider very remote. 30 min by bus to a car rental. 20 minute walk to a train station. We wanted for nothing.