Where to stay - Castellina, San Casciano Val de Pesa or Poggibonsi

Hello cailinvet, and welcome to the forum!

I stayed for a week in a farmhouse outside Castellina in Chianti and the area is beautiful. The town is small and charming and was - at the time - trying very hard to get on the tourist map. Since then they have succeeded in becoming more of a "place" so I anticipate that it has probably only improved in terms of places to eat. Several excellent wineries around the town.

I have not been to San Casino Val di Pesa so I can't comment but it looks closer to Florence than Siena so depending on whether you want a city directed stay or a rural town directed trip might factor into that decision. Check driving times (add at least 25% to google times for accuracy) to towns and/or train stations that give access to the places you want to go.

Honestly I can't see Poggibonsi appealing to anyone Italian or especially a tourist. It is a convenient transportation hub where roads and trains come together but we were never tempted to even stop driving through it. We passed through it several times driving from Castellina to other places and that was enough.

Hope that helps, have a great trip rural Tuscany is as beautiful as advertised,
=Tod

I agree with Poggibonsi not being worth your time. In addition to Castellina where we have stayed, I recommend that you also look at
Panzano. Both towns were large enough to have stores selling necessities. They have choices of restaurants, and small grocery stores.

Castellina in Chianti is fairly remote as it is accessed only by very slow and somewhat longish routes. If you stay there is fine but if you plan to drive think again.
San Casciano val di Pesa is relatively near to Florence.
Poggibonsi was destroyed by the Florentine army in 1270 and never recovered. Today is an industrial town.

My preference would be Castellina, in terms of quaintness, but as lachera said, it requires extra effort if you plan to use it as a base for day trips by car.

San Casciano (not “Casino” which means whorehouse) is ok. I spent time in it in youth since one of my best childhood friends had his grandparents’ house there, but it is a larger town and not as quaint, however it is perfect for day tripping because of the freeway right there.

Poggibonsi is an industrial town which offers a lot of amenities (even a decent size shopping mall), but it is the least quaint of all. Logistically it’s however very convenient for day trips. It’s on the freeway at the cross roads to highways to Siena, San Gimignano, Volterra, Florence, Monteriggioni, etc. and also has a train station with which you can catch trains to Florence.

Thank you so much! This is VERY helpful.

Those three towns were where I saw the villas that met our needs best, although there were a few villas north west of Florence in Monteticini Terme and Monsummano Terme that also has homes that meet our needs but I am thinking that is not the area we want to stay in ... but maybe I am wrong and that would be a great alternative area?

The "Tuscan towns" of film and TV with rolling hills, fields and rows of cypress trees exists south of Florence and particularly in and around the area called Val d'Orcia generally south of Siena. Monteticini Terme and Monsummano Terme are Tuscan towns as are Lucca, Pisa, Prato and many other towns in this area, but they are often not what people mean when they say "Tuscany".

If you want to visit wineries set in the Tuscany of films then the areas of Castellina in Chianti are the kind of place you are looking for. Anything north of Florence is probably going to be too far to visit wineries in these areas, but there are wineries all over Italy you can visit. Keep in mind that Italian laws regarding drinking and driving are very strict so a tour or wineries can always be a good idea instead of driving. These generally leave from Florence or Siena but can also probably be arranged or suggested by the place you will be staying.

I think you need to figure out which towns you want to visit and then make sure you are within easy day trip reach of those. If you are thinking about the southern places like Montalcino or Pienza they are more than a hour driving from Castellina in Chianti but over 2 hours from Monteticini Terme. San Gimignano is less than an hour from Castellina in Chianti (I've done this drive it's easy) but again more than an hour and a half from towns north of Florence.

I think what you want to do and where you want to visit should dictate the area where you should look to stay so defining that is a critical first step. If your group is not going to be doing everything together all the time you might think about staying someplace - or near someplace - larger like Siena where some of your group could explore the city while others take a tour or drive somewhere.

Hope that helps,
=Tod