Tuscany, North and South?

My preference would be 4 in Orvieto. We loved Orvieto! Close to Orvieto is Montelcino, Montepulciano and Pienza... Cortona too if you are really feeling ambitious.

I really appreciate everyone's feedback. Thank you SO much.

To sound sort of picky, but it really does make a difference... Orvieto is in Umbria not Tuscany. A lot of folks prefer to actually stay in the Val d'Orcia for their visits to southern Tuscany, staying in Montalcino, San Quirico or Pienza. Some like to stay in Siena for the larger city with more evening activities. then do daytrips south from there.

Here's a vote for four nights in Orvieto. (The duomo is considered one of the most beautiful in Italy. photo here ) And although it's true that Orvieto is in Umbria, that's just barely true. The Tuscan border is only about 10 miles away. In case you're interested, here are some photos and a few video clips from our trip to Orvieto in May 2011 and Lucca in May 2008. As for Lucca, it had been so built up for us as being an amazing place that it probably couldn't have lived up to the hype. We ended up underwhelmed. First off, it's not a hilltop town. It's on a flat plain. There's nothing particularly wrong with it. We just didn't fall in love with it like we did with Orvieto and Siena (the latter of which we visited in 2003). In hindsight, I would have picked a different town for northern Tuscany. Anyway, your mileage may vary. Happy travels.

We did a stay in the region that included 8 nights total, 3 each in Siena and Montalcino, 2 in Orvieto. While I am glad I saw Siena, I would not return. I liked the peacefulness of Montalcino, from where (as mentioned) it is easy to see the beauty of the Val D'Orcia. There's a wonderful abbey nearby, Sant'Antimo, and the drive to and from Pienza and Montepulciano is not to be missed. Asciano is nice, too, as well as the abbey of Monte Oliveto Maggiore. If you are hikers, there are some nice options in the area. Orvieto is great, and I wish we'd had more time there. Now that we have been to Umbria (spent tiem in Spello last month), I can see using Orvieto as a base for Assisi, Spoleto, Todi; so many options for touring from there. Check out B&B Ripa Medici in Orvieto. Very lovely. quiet, great price, sweet hostess, and free parking!

While contemplating visiting Florence for a day, what are the highlights that we shouldn't miss?

See the Florence section here