What a delightful decision! The Cinque Terre is wonderful, if full of tourists (though the time you'll be there would have fewer tourists). We've been to Pompeii (on my "must-do" in my life list) and Sorrento, but I have little interest in seeing more of the Amalfi Coast. One, I don't really like southern Italian cuisine, and two, I have a fear of heights that would probably leave me hyperventilating the entire time!

So that narrows you down to Tuscany and Umbria, both wonderful places to see and be. If you like Italian wine, then you might choose Tuscany, and visit places like Montalcino and Montepulciano, or the Chianti area. Or you could split your time, and spend half of it in Umbria and half in Tuscany. Of your interests, the one that I would say there's less of in Tuscany and Umbria is historical places. There's a lot of history in Tuscany and Umbria, of course, but they are more the kinds of places for wandering around and absorbing the atmosphere, rather than visiting specific important sites.

If you like wine, you might try visiting Montefalco in Umbria. When I told my friends in Tuscany I had just come there, they asked me if I had possibly picked up a few extra bottles of wine, which they were prepared to buy from me if I'd said yes.

Thanks again to all who responded. We're still torn, but I do understand we need to make reservations and SOON! I would love to just "wing it, as I usually do when traveling around the "countryside" in the US/Canada (except national parks!), but I guess this just isn't possible in September in Italy.

Henry's info about Tuscany is wonderful, and I am just empted to repeat his trips!