Unsure about Itinerary for 3 days in Tuscany

If you want to minimize car, yes Lucca, is a bit west. If not, I'd go there first thing your first morning, maybe do Pisa as well and then drive down very close to Siena for your stay for 3 nights.
If not doing Lucca, on your way down before going to your stay around Siena, do San Gimignano and Volterra and then head to your hotel. Maybe have dinner in Siena.
Spend a big portion of your day h next day, in Siena. If you have an hour left, go to Monterigionni. Super small but gorgeous.
The last do, do the Pienza, Montepulciano-Montalcino trio.
This would make an unforgettable trip to Tuscany I think

Mark,
We stayed in Tuscany for a week a few years ago. One of our favorite towns was Volterra. It is a fortress town with rich Etruscan history and very "untouristy" . It is about 1 1/2 hour drive from Florence. Get lost in old Italy walking the streets! Also, nearby is San Gimignano. It is a great place to visit and would also fit your bill for walking the old streets, plenty of shopping and places to eat & drink. All of the towers make it a very interesting place. It is much more crowded than Volterra with bus loads of people, but still worth the trip. We also really liked Lucca. It is also a fortress city. We spent our time within the walls only. We will be going back this fall and plan on staying in the same agritursimo we stayed at previously near Volterra. That is our base camp and we venture out from there. Two places we are going see that looked interesting, are Montepulciano and Cortona (looks like a lot of Etruscan history there).
We are like you and enjoy the small towns and getting the old flavor of Italy.
Have a great trip!!
Linda

Thanks for the great replies! I have added all the locations on a map.

I really think setting up around Siena and spending the 3 days near there is best, instead of going all the way to Lucca. An option could be to stop by there on day 1. I have a couple more questions:

1) Is there any experience outside of driving from town to town and walking the old streets that I should be seeking? It seems Tuscany is about 2 things: The history and the farm life/slower pace. The farm life and slower pace, anything I should experience this way? Or just stay at a Agritourismo?

2) About Agritourismo's: Recommendations? What if we don't plan to get back in time for dinner? What time would they have dinner by? (I guess some don't even do this?) I think this could add so much to the experience, which is truly what I want!

Mark,

If you have not yet purchased your ticket to Florence, consider flying Easyjet from Paris Orly to Pisa.
Lucca is a short 1/2 hour drive from there. You could then hit either Volterra or San Gimignano on your way toward Siena.

One of my favorite hill towns is Castellina, about 20 minutes from Siena. We like...

http://www.collelungo.com

But I don't know if they book for 2 nights. Try booking.com for other agriturismos in the area.

Tuscany is beautiful. Have a great time.

If the agritourismo serves dinner, which not all do, it's probably around 7:30-8:30pm.
I'm going there this summer, reviews are fantastic but have not experienced it myself:
www.agriturismopoderecunina.com
Probably too south for you I think.
Use either
www.agriturismo.it
or booking.com
I'm sure you'll find something in the region you want, in the price range you want.
If you have time, maybe visit a winery?
Also, very close to Montalcino, the Sant'antimo abbey is gorheous.

1. With only 3 nights, you need to stay in one location. That could be around Siena or the Chianti region.
2. Look at all of the delightful village possibilities and determine a daily itinerary.
3. You could drive to Volterra and San Gimi one day, Montepulciano, Montalcino, and Pienza another day, and walk Siena and drive to the Chianti region, like Castellina and Greve on the third.
4. Agriturismos don't have to serve dinner. In fact, none of the ones we have stayed in over the last 10 years have. But there are many, including Borgo Argenina in Castellina who cook with their guests one evening. It's a delightful evening, starting at 5 after you have driven around your villages, to visit, drink wine, cook, and then sit down to a sumptuous meal.
5. If you preferred to stay a bit closer to Siena, Frances Lodge is a great B&B above Siena. You can walk downhill into Siena for your evening stroll.

I'd stay in a hotel inside the walls of a place like Montepulciano that has parking and use it as a base and enjoy the many walkable restaurants in this picturesque town. You don't want to drive after any drinking in Italy so basing in a small town makes that easy and fun. And the area around Montepulciano is the best of Tuscany. (although all these other places are great too, but you only have 3 days.)

Mark,
We stayed at Agriturismo San Lorenzo, which is very near Volterra. It is a working olive farm. The picture perfect setting. They have few rooms and apartments, so very homey. They serve breakfast and dinner (in an old chapel - very fun!!). You just let them know if you will be there for dinner or not. Meals are separate, but very reasonable, as is the Agriturismo. The proprietor is wonderful. lWe loved it there and will be staying there again when we go this fall. Look up online and see the amazing countryside. From what you are saying, I am not sure how much time you will want to spend in Sienna. We found it very crowded and didn't have the "flavor" we were looking for as did the smaller towns of Volterra, San Gimignano, and Lucca. No matter where you decide to stay, you will have plenty of towns to visit within a reasonable distance. Wherever you decide to visit it will be wonderful.
Linda

We stayed last summer and my favorite towns were San Gimignano and Volterra. Siena is nice to see, but it's much more crowded than the other two.
I don't know what your budget is but we stayed at Castello di Casole about 30 min away from Siena, and we are going back this summer. We loved it.

Check that a car rental is still possible with your late flight arrival.

Sunday
Late arrival in Florence. Pick up car and stay near Florence Airport - 1 night
Perhaps a good choice here ...
http://www.cosmopolitanhotel.it/eng/index.html

Monday
Drive through Chianti hills to accommodation near Siena - 3 nights

Tuesday
Sights of Siena

Wednesday
Day to Volterra, before a late afternoon stop in San Gimignano

Thursday
Depart from Florence Airport

Mark,

This is an update for anyone that reads this in the future. We are back from our trip! WOW! We loved it so much! We planned it so well, and yet the moments we didn't plan were some of the best also!
We stayed just outside Cortona, at a small BnB (CasaBellaVista). I had pondered so much which location to stay, and wether to stay on a farm/BnB or in a small town. Well, the BnB option was perfect. Waking up each morning and being surrounded by the fields of Tuscany was so peaceful and glorious. It provided a experience and memory I will never forget. Each day we would head off to small towns and stop in some along the way. Our host gave us great driving guides to find the hidden back roads that have the best views! This was key! The drives were amazing!
Places we visited: Cortona, Arezzo, Montepulciano, Pienza, Montelcino, Siena. We stopped in a few no name towns for 5 mins here or there because they were that small! We loved this location, but also wish we had time to see Lucca, which everyone loves. But we did not feel cheated. Our favorite? Cortona and Montepulciano. Least favorite, maybe Arezzo. When we went to Arezzo it was a Italian holiday, so much was closed. They did have a fair, with antique tents...so it was nice, but crowded. Didn't get a good feel for the city. Siena is a must see and wish we had more time there. But Cortona was so charming it surprised us! And Montepulciano was the same. Pienza has many more tourists, so didn't feel as special.
All in all, we loved it so! We had GPS (a must) and then just followed some off the beaten paths with it. The sights are amazing!

It sure sounds like you had an amazing time in Tuscany, thank for the update!
I've been reading all the posts pertaining to Tuscany because I will be heading there in September.

So here is my question...
If you had to choose between Cortona vs Montepulciano, which would you pick?

The reason I ask is because I will be spending a few nights in Siena (without a car) and plan to take day trips to the nearby hill towns. When planning my itinerary, Cortona was on the list; mainly because I was reading Frances Mayes book ("Every Day in Tuscany") at the time.
Fast forward a few weeks and I just finished reading the book by Ferenc Máté ("The Hills of Tuscany"), and now I'm considering visiting Montepulciano!
Thanks in advance!

Wow, Cortona vs Montepulciano?! That's tough! They are not that far away from each other, can you not do both? Honestly. it's not that hard to truly choose. Cortona is small, we got there just before sunset, walked around, and then came back for dinner. (We had clothes in the wash at a nearby laundrymat! :P

Montepulciano, we spent 1/2 a day. Especially if you like wine, it's a clear cut winner. They have these underground caverns with wine barrels. It is very cool. The town hall and main piazza is awesome. I highly recommend going to the top ($5 euro I believe). Great views. Also, if you watch the netflix show "Medici" they film a lot in that piazza as a substitute for Florence.

Enjoy!