pieza and montalcino in the same day.... is it too much?

I don't think it's too much, depending on where you're staying. They're both very small towns, but the roads in that area aren't major highways, so plan on some travel time and start early. A fun thing to do around Montalcino is to plan a wine tour (most of them are closed during lunch) if you're into that sort of thing. There aren't a lot of "major sites" in either town, but both have a lot of ambience.

Montalcino is tiny. Park outside. Parking is expensive in the pay lots but we found a free lot right outside the maingate. The wineries are fun but most need a reservation and good directions. Barbi doesn't require a reservation and is free and a short drive (most wineries have gravel roads) with a nice tour that takes about 30-40 minutes with tastings. See their schedule. Orvieto is a great hilltown that we really enjoyed.

Hi Sasha. You can certainly visit both places in one day. I'd recommend Pienza in the morning and staying the night in Montalcino. When we were there in early May traffic was very busy, and the most stressful part was arriving at the hilltowns and finding parking etc. Montalcino is mostly about the wine. There is an amazing view wall at the far end of town, with park benches and you can see forever. The fortress is nothing special (save your money and skip the view from the top and take the free view mentioned above) but an OK spot for winetasting. For us Montalcino was best late afternoon and evening. A glass of wine at a sidewalk cafe, people watching. Good restaurants. Pienza has a few great sites. The Church and also the Palace beside the church, a great view wall. They have an astonishing flowermarket on Sunday's. Enjoy. BTW, the drive between Montalcino and Pienza is breathtaking.

We did Montalcino, Pienza and Montepulciano in one day easily. We didn't rush, took our time and enjoyed all three immensely. We are not into wine at all and found all 3 towns incredibly charming. We were there in late June '06 and none of the towns were crowded at all, in fact there were hardly any tourists at all. We'll be there again in 2 wks and we can't wait!

Just got back two weeks ago and we hit all three towns in one day, no problem. It was very leisurely. We were coming from a little town called Monte Benichi which is between Siena and Arezzo so we had about a three hour round trip drive. If you go to Pienza, try to eat at "Latte de Luna" ("Milk of the Moon")and if you eat meat, try the roast suckling pig. It is to die for. You will not get in unless you have a reservation or are very lucky. Charming indeed. No one is there ten minutes before they open and then all of a sudden, the patio is full!