Home Base in Tuscany?

Have you looked at this website https://www.chianti.com/itineraries-in-chianti/ ?

One small town I know of is Panzano in Chianti. Not sure what kind of hotel or AirBNB accommodations may be available there, though.

Someone recently had the same question in this forum here is the link to the responses
https://community.ricksteves.com/travel-forum/italy/tuscany-hill-towns-where-to-do-base

Dear Friend and I used Montepulciano as a base for daytrips, this past summer, July 2016. We stayed in the beautiful, and beautifully located Politian Apartments, which are at the "top" of the town (with full kitchen, clothes washer, comfortable living room, and gorgeous view out over the valley). The lovely owners emailed very specific and careful instructions about how to drive up the "back" way into town, to our spacious apartment, and we always found parking on the street within a few meters of the front door (the owners gave us a placard to place in our car which gave us parking rights in town). Thus we had a gorgeous town to return to in the evenings, with great restaurants, cafes, and shops in very easy walking distance, yet we were fabulously well located for daytrips throughout Tuscany (Siena, Montelcino, Pienza, Bagno Vignoni (sp?), etc. etc.).

With the luxury of a car I would split 2 weeks into 4 locations moving from south to north ...

Montepulciano 3N
Agriturismo near Poggibonsi/ Monterigioni 5N
(for Florence, Siena, San Gimignano)
Lucca 3N
Cinque Terre 3N

Nice central base for all of Tuscany.

http://www.collelungo.com/en/

Just outside of town. Up on a hill overlooking the vineyard.

Short drives to San Gimignano 45 min. Radda 15 min. Greve 25 min. Montepulciano 1H15 min. Florence 45 min. Siena 25 min. Monteriggioni 15 min.

I would rent a place in a hill town with good evening access to restaurants etc and with parking; we spent two weeks at an apartment in Montepulciano and it was a great base. Then you can spend some time in the town of choice and days driving to some of the many places in the area. San Gimignano is tiny not a 'larger town' but wouldn't be my choice. Siena is a great place evenings and there are hotels within the wall with parking but you do have the larger city to get through before hitting the countryside. If you stay in hotels then staying in 2 or 3 locations also makes sense although I hate the wasted time in moving and personally prefer an apartment and kitchen even if we only have breakfast there.

I recommend Chianti as well.....we stayed here 4 years ago and loved it: http://fattoria-tregole.com/ It is a working winery. The owner, Edith, is amazing. We rented a car and were able to do day trips which was quite an adventure!

The area between Montepulciano - Pienza - Montalcino would be ideal as long as you have a rental car. We stayed in Pienza and it is an ideal small Tuscan hill town with a great view and wonderful countryside surroundings but any of the above 3 towns could work.

Would not spend a full week in the Cinque Terre, maybe 5 nights MAX there and spend more than a week in Tuscany where there are many more things to see and more daytrip options. Most people stay 3 nights and find that sufficient so even 5 is a long time to stay there.

San Gimignano is a actually a very small village. Not sure where you got the idea that it is even comparable to Siena.
Check some ideas in the site below. It's hard to give advice, as the choices are endless. The only advice I can give is to first decide which towns you want to visit during your stay, then find a home base in a town logistically well placed. A place Reasonably close to the Siena-Florence freeway would be a plus. Use google maps to estimate distances from your base to the places you want to visit.
http://www.borghiditoscana.net/en/

Thank you! Thank you! everyone for all of the incredibly helpful information!
Regarding San Gimignano........A friend was there a few years ago and described it as being busier and a more touristy as compared to towns such as Montalcino, Pienza, etc. (Perhaps this was just her interpretation? Or my misinterpretation of her interpretation!)

I do have a few more questions:
Has anyone stayed in Montalcino?
Has anyone stayed in Greve?

Regarding dividing our trip into four stops:
In doing so, would it be easier to stay in the same type of accommodations in each stop? Such as apartments or agriturismos?
Or would you stay in a different type of accommodation in each location?

Again, thank you for helping to make our anniversary trip a very special memory!

Thank you Roberto.......Very helpful link! :)

Rentals in Tuscany are usually for a week and usually Sat to Sat although not all do that. Some Agriturisimos take people for a night or two but rentals usually mean longer commitments. If you want to move around, then you are talking hotels and B&Bs. It also means you are touring with your luggage in the car some of the time which is quite unwise. I would for only a week not have more than two bases so you can stow valuables and then tour from there. checking in and out and moving all the time really chews up time and one night in a hotel is not 24 hours -- you check in at 3 and out at 10 or so.

San Gimignano is a tiny town and has become a tourist trap because it is too small to support the number of people flowing through it. It is actually rather charming at night after the buses leave but I would never base there. Do a day trip to it and Volterra on one day.

I also agree that a week is far too long in the Cinque Terre. We hiked it 30 years ago before it was turned into a crowded tourist trap. It is still beautiful but 3 nights with two days for the trails would be my maximum and two nights with one day devoted to the trail from Montorosso to Riomaggiore would be plenty. You can easily cover the trail (if it is open) in one leisurely day with plenty of time for the villages along the way. If you cut that part of the trip to 3 nights, you could then rent in Tuscany for a week and also have one or two shorter stops.

Jane: Airbnb and Homeaway websites have changed the typical rental term. Finding 3 night rentals or even less is quite easy now and almost every property available is being listed, they are dominating this market. Homeaway and VRBO are the same.

Agree with mreynolds. We did the same thing...stayed in an agriturissimo near Pienza which is a beautiful and centrally located Tuscan town. (The town has a "terrace," which is a essentially a lovely pathway and wall with gorgeous Tuscan vistas for picnicing or enjoying a sunset.) It worked great for day trips to Florence, Siena, Montalcino, Montepulciano and more. We stayed here and would recommend it:
www.tenutasantopietro.com

I was expecting spartan Italian breakfasts, but it was an incredible buffet every morning.

I apologize for the delay in my response........Got a little off-track during the Holidays!
Thanks again to all for such concrete suggestions! We're re-evaluating our itinerary.....Possibly staying in 3-4 locations? We wanted to avoid a lot of packing/unpacking. However, it does make more sense in order to avoid lost time in back-tracking.
Has anyone stayed in Montalcino? Just read an interesting book written by a women who packed up her life in Australia and moved to Montalcino.
Thanks again and Happy New Year!

We love Montalcino! We have been there a few times and last time we stayed here: http://www.canalicchiodisoprawinerelais.it/web/index.cfm?id=0E97327C-789D-4A5E-88F742FAB6074C5D&home
You will definitely want a car in Tuscany so that you can get around. This particular place driving distance to the hilltop town. There is a Coop in town and we were able to get groceries there and then cook back at our hotel. They even have a BBQ so we could make bistecca.

I have also stayed at Le Cetinelle just outside of Greve and loved that as well. It's a peaceful agriturismo and you can rent on a nightly (as opposed to weekly) basis. Greve is a great town with lots of restaurants and shopping, but it's not a hilltown.

I would recommend either of these locations.

EVERY town that has been suggested is amazing and you will love driving through each of them ! You don't need to stay IN a village because you will drive to ALL of the towns that you want to visit.

Find an agriturismo/winery that you love and stay there ! We love Cretaiole, closer to Pienza, and Borgo Argenina, close to Greve.

Drinking wine at sunset and drinking cappuccinos in the morning as you overlook the vineyards is enchanting ! And you get to cook with the owners, Isabella and Elena. It's such a memorable evening as you cook and laugh with the other guests and then sit down to a delicious meal among new friends !

I really like Lucca* as a home base. We've used it as a starting point for daytrips to cinque, bologna, Florence, pisa, siena, san gimignano, and volterra. There are also some great villas, bargas, etc. in the vicinity of Lucca, and Lucca itself, that make for great lazy days when you don't feel like a long day trip.

*eta but not necessarily inside the town of Lucca.

Thank you all for your suggestions. I think we finally have an itinerary! I would appreciate any recommendation of a hill town in Southern Tuscany that would be good for a 5-6 night home base? Thanks again! :)