Where to stay in Tuscany for 2 weeks in November?

This is where you want to stay. I have stayed there twice, most recently last year. It is in the heart of Chianti Classico country about half way between Florence and Siena and is an easy drive to both. The restaurants and shops may not be within walking distance, but the town of San Donato in Poggio is about a five minute drive away. There are some very good restaurants there. www.chianticortine.it La Canonica di Cortine

Greve

Everyone seems to really recommend between Florence and Sienna. I appreciate it. My only concern is we’d like to head to Pisa, Lucca, and the coast for a day or probably 2 and thats the opposite way. Also further from Florence then I’d prefer. Really like Greve though that is probably number 1 spot for me.

I’m trying to go to one spot because I’ve never done that before. Would like to make friends with the local baker, hit up some spots multiple times, and overall not rush anything. If we go to 2 spots why not 3 or 4? If I commit to doing more then I have a hard time not trying to do everything, then you are constantly rushing to see more. Plus it’s a slow time of year and if we rent a place for 2 weeks we can probably get a pretty good deal.

Bakery not a big deal at all that was just an example. Just mean its nice to have an espresso or glass of wine and BS with someone you see more then just one time sometimes. I'm not planning on meeting someone I'll talk to ever again or anything.

I'm not a fan of driving the day of arrival due to being extremely tired usually. So we will likely stay the first night somewhere then rent car the next day. Which is likely Florence if we fly in there or somewhere else along a train route.

Plus, the biggest thing is we'll have 3 kids under 7. Its nice to settle in which we rarely do on vacation. I mostly want to walk because its nice for one person to stay back for naps while the other can be out and about. If everything is necessary to drive then it makes that harder. Also, we both drink and uber/ taxi with kids is a PITA and I'm not gonna have them not in car seats in Italy. So its nice to walk to dinner and be able to have an extra glass of wine without a worry a couple of times.

As Hungryone likes to say its not necessary to try and see it all every time. I'm planning on being hindered quite a bit, and planning to try and just enjoy the small things here. I want to feel like I live there for a bit and not just dropping in to visit. It may be too romantic of an idea, but hey its worth a try.

Not sure on flights yet, Milan isn't out of the question with a fast train to Florence. Hopefully Florence but with 5 airfares (using points but still) I'll be working with our options.

We stayed in an estate in Kent, England that was amazing but it was a couple miles from the closet pub and further to anything that sold groceries or what not. Looking to repeat that experience but with places within walking distance. I don't mind walking close to a mile, closer to 1/2 would be preferred. But if you are in the country you are just really stuck with only one car. I also like to wake up early and usually take a kid or two to breakfast while my wife gets ready and holds on to the slowest kid. Same thing with dinner. Nice for one to head out with whoever is ready and grab a cocktail while the straggler catches up.

There's quite a few rentals all around with a yard/ pool (don't need that obviously) that are well within walking distance to towns. I just wasn't sure what area is the best to stay in to most easily see the most. I fully understand Tuscany is 3+ hours driving north to south so I'm not expected to cover everything nor be in a perfect spot to see everything easily.

Gotta talk to Ciccio.

Ha, no I'm not planning on buying a place there. I would never own a home in another country at this point. Just more hassle then it would be worth.

I simply meant I like to go on vacation and imagine how different your life would be living wherever you are currently visiting.

Greve is a great location. It has a great enoteca, a butcher shop that opened in the 1700 or something like that and they're on a nice big piazza. It's a town I've been to several times and would certainly like to spend more time in. In our stays in Tuscany we've stayed in a small village (Gaiole in Chianti) and I want something a little bigger but not on the level of a city.

There are a couple of bakeries right on the piazza in Greve.

I will say this about Greve: It has the best wine store I have ever been to - Enoteca Falorni.