A Month in Tuscany

One thing to flesh out: do you intend to have a car throughout, or just want the option to easily (how easily?) get to a car rental office occasionally? One way to drastically narrow down your options would be to focus on the trasnport part--like just limiting to places with train stations in walking distance.
Also, you have roughly focused on one part of Tuscany previously, so you could look up what kind of day trips you want to do and choose a more confined area. In summer, I would imagine being close to the coast might be nice. I can just imagine being a teen girl again and walking a lungomare (lucky them!). Last, in summer June and August are very different so I'd share that as well.
I do think Montepulciano would be a bit small and limiting (it would be my dream at 50ish, but I'd go bigger with teens). Here is one random idea to help rule in or out what you are looking for: the town of Piombino is on the coast and has a train station, plus is the ferry port so you have lots of options. It is close to countryside for using that car well. I have not been there but have been in the area twice and it just popped into my head. This would be very small town and coast focused, and I just am not sure if you have settled on exactly what you are looking for yet, but I am sure the right place is out there.

Thank you so much for this reply. We'll be there for the month of July and currently have a car reserved for the entire time. I just realized the palio is happening during our stay there so I'll do so research about options on the feasibility of being in or around Siena at that time. While visiting a coastal region may become a part of our visit, it wouldn't be top of the list as a base. Where we live is quiet and coastal. To answer your question about proximity to a train station - within a 30 to 60 minute drive with the option for overnight parking would be ideal.

Americans Cana be car centric. But, If you do a search on Tuscany bus lines you can find maps and a travel planner. The English option is a box in the lower right corner of the page. Assign the girls to investigate the options. A car is great, but depending on their ages enabling a few bus trips on their own or with a parent without a car could be a hoot, and very informative. I always use buses in the Dolomites and it works great. Towns are all connected, if trips slower than by car, but no parking problems in ones with pedestrian only then/city centers.

for example:

https://www.at-bus.it/en/lines-and-timetables

When I looked around for a spot in that area that offered many options for bus and train transport, I chose Siena. We have booked a lovely apartment for two weeks here on Vrbo: https://t.vrbo.io/nvF28XlA7Wb.
The town has several escalators to help with the hills. I will be there in April and can let you know how everything went. Good luck!

To answer your question about proximity to a train station - within a
30 to 60 minute drive with the option for overnight parking would be
ideal.

Your best options for main line train service will be Florence. Siena is also good but on a spur line so a lot of routes from there will have you changing in Florence
Some other towns that have train service-- Lucca, Poggibonsi, Buonconvento, Chiusi, Arezzo.
Montepulciano does have a train station but a bit outside of town. I don't know which might have overnight parking.

I agree with above- Montepulciano is lovely and interesting but pretty small for a whole month.
I would consider staying in Siena- even if during the Palio- THAT would be super cool for your kids to see.

I would think Siena meets your requirements, especially for the month of July and the Palio (July 2). Siena has been our base since 2018 staying one to three months each year. (Except for 2020, of course.) It is a very walkable and safe for all ages. We only use public transportation but have rented a car for a couple of days when necessary. Staying for a month you will find the locals will treat you differently and enjoy sharing their culture and telling you places and activities that your younger teen girls might like. No matter where you stay it will hot, so make sure your rental has good A/C.

July is hot as hell in the interior of Tuscany. If you live on the Ocean in the US, maybe you haven't experienced that kind of heat every day. You can be anywhere you like, as long as you have air conditioning and possibly a pool. I’d look for a hotel or farmhouse with parking and pool. You can use booking.com and filter for accommodations with AC, parking and pool in any area you like. Make sure you look at the reviews because some hotels/apartments/houses have AC that is ridiculous at best. The best place to stay depends on the day trips you want to take. Try a place within easy reach of the freeways (Siena-Florence, Siena-Bettolle, etc.) because those country roads are slow. Places might look near on the map, but on most roads you are lucky if you can drive over 40 km/h (25mph) with all the curves and towns, all with low speed restrictions.

Thank you all for taking the time to respond. Given the feedback and some further exploration, I'm leaning toward something close to Siena with AC and perhaps a pool. Does anyone have additional properties they'd recommend? I'm seeing some apartments and farmhouses but I don't know the area well enough to determine where they are in terms of true accessibility to either the town or the highway. A month in Montepulciano is still my dream but that will give me a reason to return!

Barring specific recommendations (possible, sure, but chancy and slow), the only way I know to check locations is to just slog it out with google maps. I anyways make a list of places I want to see first, then I plot them all out to triangulate the best location somewhere in the middle. This strategy also gives you a leg up when it’s time to navigate on day trips.

Valadelphia's strategy is the way to go.
Plot the places you want to see. Then find an area somewhere in between those places. Then zoom in Google Maps and look for "Hotels" or "Agriturismo". Some accommodations, especially agriturismo (i.e. farmhouses) are hard to reach, because of the curvy roads, so test the driving times from the prospective locations and the places you want to see. Google Maps is reasonably accurate in estimating driving times, however Google uses the input that Google users drivers send to Google, and locals drive faster than you will be, so Google Maps estimate are generally understated by about 10-15% (so add 10-15% to the time estimated by Google). There are two freeways in the Siena area. The one that goes from Siena to Florence, the one from Siena to Bettolle (and eventually Perugia). There is also one (half finished, off and on) going from Siena to Grosseto. If you are reasonably close to one of those freeways entrances, you can drive to farther destinations (even in the region of Umbria) quickly once you are on those freeways. Siena or any town is nice because you can walk and stroll in town in the evening, but it is unlikely you will find apartments with pool in town, for a pool (which your children will enjoy in July), you need a villa or farmhouse a bit out of town, but some are sufficiently close that you can drive to the closest town in minutes for dinner and stuff.

Hello KayD. and welcome to the forum,

This is quite a question to kick off with. I have a couple of thoughts on this and for context I have done week long stays in Tuscany - specifically near Castellina in Chianti - and stayed for a month in Lucca in the fall.

A few thoughts:
Italian towns also often have festivals and events and these can be great to be present for, but trying to book a place for a month can often overlap with a really booked up week or weekend that can ruin your plans. Or make them much more expensive than it would otherwise be. In late October/early November Lucca hosts a comic-con that brings 8x the normal population to the old town and the availability and the prices for that weekend are crazy. Siena's palio will do that to the town as well.

Places that are accessible by train and charming will generally have tourists. There are nice "real" Italian towns off the tourist trail but you also have to consider that "real" Italian towns come with considerably less English. English proficiency falls off with age and distance from tourist oriented endeavors. Italians are 100% committed to working with you and making transactions happen so you will get coffee and groceries. But you will certainly lose the ability to ask questions or get the whole story if your Italian isn't at least beyond a few words.

Also places that are small and super charming can mean only a handful of places to eat and maybe on Sunday no place to eat except the bar or pizzeria. (Sundays in Italy are taken seriously even in fairly touristy areas.) So as charming as the tiny Tuscan hill town seems for a few days a full month may seem like a different thing.

When you're discussing "Tuscany" people generally mean rural Tuscany south of Florence that is the Tuscany of film and photos. Lucca, Florence and Pisa are Tuscany as well but not the rolling hills with cypress tree lined lanes. But even this area is really to large to fully explore from a single base. The area I have looked at as the closest to a compromise is the area around the small town of Buonconvento. It is about 30 minutes to Pienza and 45 minutes to Montepulciano so it is in day trip range for me. It has train and bus service to Siena or is about 45 minutes away. It's a bit far to Volterra, San Gimignano and Rada but might be worth a day trip chaining several locations together. It is the closest to "middle" area between north and south that also has some bus and train service. I know there are several agriturismos in the area but I don't have any recommendations.

Make sure every driver has an IDP and you read up on ZTLs before visiting somewhere.

Have a great trip!
=Tod