Pienza and San Gimignano in the same day?
 

Will be staying in Florence for 4 nights and plan to take one day to rent a car and visit some Tuscan towns.
Since we were only renting the car for one day we were thinking of doing at most two places. The two highest on our list were Pienza and San Gimignano.
I'm wondering if doing both is possible if we leave Florence early, head to Pienza, then go to San Gimignano in the later afternoon (stopping for lunch somewhere along the way)?

I'm thinking we'd get around 2.5-3 hours of actual walking-around time in each city.

Would that be too rushed? We really can't bring ourselves to just pick one but if we had to what should it be?

You can walk side-to-side in Pienza in about 5 minutes.

Doing both in one day ounds like a good and doable plan to me. Both towns are quite small, so within 2-3 hours each you can cover them well.

SanG and Pienza would not be my choices, but it's doable. It will be more than 4 hours of driving, not counting any distractions/detours.

<< I'm thinking we'd get around 2.5-3 hours of actual walking-around time in each city. >>

These places are not cities. I'm not sure what you'd do for 3 hours in either town. The area around Pienza is very pretty.

I spent a couple of hours alone in the convent's wine store tasting wine and eating various salamis and cheeses in San Gim! After seeing the main drag, side roads and squares, churches, etc., I wandered the back lanes where local children were playing and climbed the walls where there were beautiful homes and views. I only spent about 4 hours in San Gim but could well have spent more!

I scond everybody above: Pienza is tiny. But there are other nice places along your itinerary like Monte Oliveto Maggiore http://www.monteolivetomaggiore.it/lang1/index.html
Buonconvento, Montalcino ......

Yes, it can be done. But Pienza and S. Giminiano are about 1h 45min driving distant; consider that while highways (Siena to Florence and Florence south direction Rome) are relatively fast driving, ordinary roads (from the highway to Pienza, Pienza to Siena, Poggibonsi to San Giminiano) are slow drives. IMHO visiting Montepulciano and Pienza would better spend your time, but if you need those two places you can do it.

Do San G. and Volterra instead--Pienza cannot compare to Volterra.

I'm not sure what I'd do in Pienza for 2-3 hours other than stuff my face with cheese, but sure, you can do this and more in a day. Just know that renting a car for a single day can cost about the same as a 3-day rental.

All right, sounds like I actually have plenty time. So now I'm wondering if I should toss in a 3rd stop? Siena would be an easy one but we have visited before several years ago. I'm wondering about either Montepulciano, Volterra, or just drive back to Florence from San G along the Chiantigiana.
Or not sure, maybe I'm overloading it now.

YOu miss the point.
Pienza is a long way from San Gim. and may not be your best option. Forget Pienza and visit somewhere closer.

Siena is not an easy "stop." If you haven't been there in several years, you'll be amazed (and dismayed) with the amount of traffic around/outside the city. You can't drive into the historical center, so you have to get through the traffic, find the parking, and then walk into the center.

I agree that a combo of Pienza and SanG is not great. I would pair either town with another that is relatively close, i.e., Pienza plus Montepulciano or Montalcino -OR- SanG plus Volterra or somewhere in Chianti like Castellina or Radda.

(Since I'm not a big fan of either Pienza or SanG, if this were my trip, I would be focusing on the pairing options.)

Are you renting the car the day prior to this driving day and then returning it the day after? If not, you need to investigate the hours that the rental office you use opens and closes. That will set the limits on how early you start from Florence and when you need to be back. Personally, I don't like driving in the dark unless I'm very familiar with where I'm going.

The Duomo in San Gimignano has some of the greatest frescoes in Tuscany, and that's saying a lot. Please time your visit for the opening hours.

So, we are wanting to see the Val D'Orcia (hence Pienza). And we figured since we are going so far south we could stop at San G on the way back.
Is there any reason combining those two would be bad beyond the driving distance?
We are picking up and dropping off in Florence that day. So it's not like we'll be stopping overnight.
Sounds like most posters are not fans of either town.
Any particular reasons beyond the fact San G is very busy?
Are there 2 other towns we should be pairing instead?

Well, my family tomb is in San G so it is the place where I will be likely spending the longest part of the present and future centuries. Apart from this and the crowds, there is no reason I should not like San G, a very beautiful place that in most countries would be considered as a major tourist destination, worth two or three days of your time. Also Pienza, while tiny, is exceptionally interesting for the only German gothic church in Italy and a landscape on the back of the village that you could spend a couple of hours just watching. Only consider that you will be spending about half of your time driving.

I've based in Pienza a couple of times. It's easy to get in and out, there are lots of cheese shops and several other things to see.

http://www.palazzopiccolominipienza.it/en/index.html

I think I would drive there first and perhaps have lunch, then head to San G. and spend the afternoon. You could even have dinner before returning to Florence (assuming you don't turn the car back in until the next morning). I think by arriving San G in the mid-afternoon, you might miss the daytrippers (tour buses).

Yes. The time spent driving is something we've thought of. But we're wondering if the driving itself will be enjoyable given the scenery.

Kybourbon,
Yes. That's actually my plan. Get there at the tail end and let the tour busses leave.
What time is that normally.
We were actually thinking of dropping the car off in Florence that night at the airport. They seem to be open late for that.

In this area of Italy it is not the destination but the journey.

http://www.slowtrav.com/italy/tuscan...ng_tuscany.htm