5 nights in Tuscany/Umbria

We just spent five nights in Tuscany earlier this month. We stayed at a nice bed and breakfast kind of place in Chianciano Terme. It was easy to make day trips to many great hill towns from there. We suggest you stay in no more than two places, one closer to Volterra/Siena and one closer to Montepulciano. That would save you a lot of packing and unpacking time and hassle. We enjoyed lots of good wine everywhere we went, including Brunello in Montalcino. Some of the best wine we had was simple table wine in restaurants in small, non-touristy hill towns, where we were the only Americans in sight. You'll be so close to Pienza, you should visit there. It is a small and picturesque place, both within the town and looking out over its walls at the countryside. We've been to Cortona and Civita di Bagnoregio. You may want to skip Cortona, but Civita is so unique it's worth a visit, even if you don't stay there.

Is there a reason you want to change location each night? I prefer to stay in one place and do daytrips. We stayed at Agriturismo Marciano, just outside Siena, and it was a great location to tour the hill towns during the day, then have a base to come back to at night. This Agriturismo is a winery and they also make olive oil. They have to-die-for optional dinners that pair their wines with local organic food.

We are certainly open to staying in one place the 5 nights we are there. Sienna looks the most central. Or two nights somewhere and two nights somewhere else.

Kellie,
This may give you ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Civita is so tiny....it can easily be a half day trip (or less) from Orvieto.

I second the idea to stay in one or two locations and take day trips to these locations. This will be much easier than carrying around all of your luggage and switching hotels each night.

Andrea,
I am so glad to read your post about the winery place you stayed outside Siena. I am working on our itinerary through Rome and Tuscany and we would love to stay in a winery. Will definitely check this place out, any other suggestions you have about it?

Thank You all for your replies. So far, we think we'll be stay 2 nights in Montepulciano and 3 in Orvieto. Any recommendations of a good argriotismo (sp??) in either area? We're spending a month in Europe and for some reason Tuscany is the toughest to plan!! We'll be traveling by car for these 5 days.
Many Thanks.

A wonderful agriturismo, outside of Orvieto, is Locanda Rosati. It is beautiful, comfortable, and welcoming. Check it out. The communal dinners are fun and Giampierre
serves his own wine with the meal. Afterwards, there is grappa and lemoncello, of course.