We will be renting a car in Florence and driving through the Tuscany wine region June. We have 3 1/2 days and 3 nights to plan for.
Points of interest that others have recommended that we are interested in visiting are San Gimignano, Greve in Chianti, Sienna, Val D'Orcia, Montalcino, Pienza, Montepulciano.
So the question:
If this was your trip, how would you delegate your time (intinerary) and which would be your preferred areas to stay in? Not sure if we should base in one place for two or three nights or stay on the go from north to south?

We will be leaving from and returning the car in Florence before heading to Venice (we have debated drving through to Venice at this point, from other recommendations but have not decided on that yet)?

Thank you all again for your help and wisdom on these questions.
-David

If this were my trip, I'd base in an agriturismo in the environs of, and to the south of, Siena (because it is most central).

With 3 1/2 days...
1 day) Monteriggioni, Volterra and San G (in that order)
1 day) Val d'Orcia (half the sites)
1 day) Val d'Orcia (other half of the sites)
.5 day) Siena itself

Hello David, I would stay in one location--probably in San Quirico at Palazzo del Capitano. I would see either Greve/Castellina or san Gimignano on your way south--not both. There is no reason not to drive to Venice--why mess with trains in Florence? From San Quirico you can easily see the other destinations incluiding Siena one day--hit the Abbey at Oliveto Maggiore going or coming that day. Have fun !

I personally loved Montalcino and Sienna - Sienna being more "urban" (if you can call it that) but still beautiful with plenty of restaurants/bars for its size. Montalcino has lovely wineries to schedule tours at and is a hill-top city so wonderful views. I would try to get at least one night there.

Side note - I think Venice would be quite a distance to drive from Florence/Tuscany. Also, note that that a GPS device is LARGELY helpful driving in Tuscany - lots of unmarked small winding roads.

Thanks for all the great advice. One additional question:

We wanted to visit San Gimignano and Sienna on the drive south to the Montalcino-Pienza-Montepulciano circuit(where we'd like to stay 2 nights)
Of my three days, would anyone advise that I stay somewhere en route? Sienna perhaps?
Thanks
-David

I'd visit only San G on the way southward - it deserves the better part of a full day or at least a half. Siena is about an hour from Montalcino and is also a full day or at least a half. (San G is maybe 1.5 hours from Montalcino.)

I agree---stay at one hotel--see san G. as you drive south.

David, I posted a question about our trip to Montalcino in May. Click on my name to find the post and some great info that's been posted so far.

very ambitious i would do 1/2 my time in sienna and sanG and the other 1/2 in pienza, montalacino and montipulciano. great walking towns. if you visit a winery or have lunch at a restaurant you may not get further due to all the good wine. i would suggest do the last 3 mentioned towns and see arezzo for a day instead of sienna and san G save for another trip. do try the vino noble wonderful

Great info everyone. Special thanks to Bob, TuckH, and Grasshopper as you have responded to multiple posts for me.

As of now, I am looking to pick up my car in Florence in the morning, drive to San G on the way to my hotel south of Sienna. I'll probably dabble around town and somewhere close that day and go to Sienna for a fuller day the next day. Other than the time spent in Sienna, I'll spend the rest of my time between Montalcino-Pienza-Montepulciano. I'll then drive to Venice per Bob's recommendation and drop my car.
Last question:
I loved Bob's reccomendation of San Quirico at Palazzo del Capitano and then I found Bob's super list on another post of other great places in the region. Great resource, but all of those locations looked perfect. Am I just overthinking this whole ordeal? Thanks again.
-David

I don't think you are overthinking the accomodations issue.

My sister is visiting the area in early June and a couple of the places she wanted to stay were booked up by last month.

>> Am I just overthinking this whole ordeal? <<

Yes you are.
And please, please do not call it an "ordeal"!

I agree with Bob about driving to Venice. It's easier than dropping the car and getting yourselves to the train. If you drop the car in Piazzale Roma in Venice, it's easy to get a vaporetto to your hotel.

And I'd pick up the car on the outskirts of Florence, maybe the airport. Driving in central Florence is greatly restricted. You don't want to get a ticket in the mail months later.

I agree with the other advice, though you could also consider staying in Pienza at Il Chiostro di Pienza.

We did spend 1 night in San Gimignano and were glad we did. This small town gets very crowded during the day. We were able to explore it in the evening and in the morning.

Thank you TuckH. You are correct, going to Italy should never be considered an "ordeal".

Another incredibly great place where to base yourself is this one: www.quattrotorra.it/ - an incredibly beautiful 14th-century castle in original state (plus the amenities of modern comfort, of course) on the outskirts of Siena. For me, clearly the top accomodation all over Tuscany.

The most wonderful place that I have ever stayed is the Castello di Spaltenna in Gaiole. If it is in your budget, it is incredible and it is the perfect location to see all of the places you mentioned. We stayed for there for three nights and were able to see Sienna, Greve, Montalcino, San Gimignano (my personal favorite) and more. There are even some great restaurants right in the town of Gaiole. This place was perfect in every way!

Ciao, Franco! Quattro Torra looks quite spectacular. Thank you for the link! eks