Tuscany/Umbria

It's all a question of personal taste, but if I had to make a choice, I'd skip San Gimignano and try to keep Assisi in my schedule. San Gimignano is less impressive than it looks on pictures and it's very, very busy with day trippers. The interior of the San Francisco basilica in Assisi is a beauty: a picture book of frescoes, especially in the Lower Basilica.

Hi, I would just add that three hilltowns in a day is a lot and depending upon what time of year you are traveling, do Civita first before it gets too hot since the path up to the town is long and has no shade.

Of the towns you mention Montalcino is the most out of the way. Given that though, your round trip distance from Perugia/Montepulciano/Pienza/Montalcino/Perugia is only about 130 miles.

I would not skip Assisi nor Siena, both great towns if you like what they have to offer (see guide books).

Here's another 130 mile round trip for your consideration: Perugia/Foligno/Montefalco/Todi/Orvieto/Perugia. That's a lot to see in a day but you might consider it.

Day 1. Towns along the way.

Florence-San Gimignano-San Donoto-Greve-Panzano-Radda-Castellina- Colle di val D'Elsa Spend the night here. The SP 222 is from Greve-Castellina. All of these are worth seeing, but if I were to choose, it would be SanDonato, Greve, Radda There isn't a way to see them all, so pick 2-3.

Day 2. Colle di Val D'Elsa-Montalcino-Pienza-Montepulcino-Orvieto-Perugia.
Again pick 2-3.

I just can't imagine why anyone would even consider going to Civita and Todi in place of Assisi. Assisi houses one of the premier works of art of the Italian Renaissance, namely Giotto's frescoes in the basilica. It's also an attractive medieval hill town. Todi, while attractive, has nothing to equal it. Civita has nothing.

We stayed in near Pienza and I would not recommend that it's worth stopping there -- not much to see, especially compared to Montepulciano and Montalcino. We hit Sam Gim on our way down from Florence and just walked through the town fairly quickly, so we thought it was worth the 1-2 hour stop, but if you're short on time, I'd still prioritize the other places (we're also winos, so we loved the Montalcino area for tasting). Unfortunately, we didn't get to Assisi, but we thought Civita was pretty interesting -- you do feel like you're really back in time with this little village -- but as with everything, some will like it and some won't.

Hey gerri, there seem to be several San Donatos. Which one are you reccomending?

Tim...

San Donato in Poggio.

My last trip I visited Assisi and now in August I be going there again. Its a beautiful town with beautiful art work not to be missed.

Thanks for all of the thoughtful responses!

So it sounds like I should try to fit Siena and Assisi in. I'm sold. Is it feasible to do a taste of each of those in half a day? The itinerary would look like this:

Day One:
1. Siena
2. a couple other small places (Montepulciano + Montalcino) OR San Gim

Day Two:
1. Assisi
2. a couple other small places (Todi + Civita) OR Orvieto

Before you get into something like nonrefundable deposits, look on viamichelin.com for driving times between places you hope to do in the same day. The accepted wisdom here is that you should add about 25% to their estimates. Don't forget to allow time for finding parking.
Personally, I would not try to do Orvieto the same day as any of the other destinations you are considering. You can easily fill a day there, or even two. The Duomo is awe-inspiring, both inside and out. There is a small museum near it that houses some good Etruscan artifacts. We've never made it to Patrick's Well or the Etruscan underground tunnels in two day trips there. You'd want to allow some time just for walking the streets of the medieval town.

I agree with Rosalyn about Orvieto. Much to see there and also in Assisi, and you could easily spend much of the day just visiting one town.

While I agree that Orvieto can be done in a half-day, Siena requires a full day - just because it's so big, so crowded, and so hard to park. Watch out for ZTLs while seeking a lot with any spaces in it. You need to add a lot of time for parking and walking to the historic centers.

It would certainly take you two hours to drive from Orvieto to Assisi. Perhaps you should select some lesser towns that aren't so far apart. (For example, I thought Cortona was small, uncrowded, and nice, and they have Fra Angelico's "Annunciation".) San Gim is only small in comparison to Siena. It is proportionately just as crowded. I would not recommend doing Siena and San G the same day, despite their proximity.

You can rent a car at the Perugia airport. I've heard automatic cars costs more and are hard to find. Can either of you drive stick? You might be okay if you are not picky about where to rent from.
I've only been up Montalcino so far but I am about to go to Montepulciano in a few days! We are also staying in an similar place but near Citta Della Pieve.
Also, I read on another post once - you will not remember the things you did not do. When you trip is over, you will have wonderful memories of what you did.