I will be in Italy for 21 days. Honeymoon. We're touring around: Rome - 2 Hilltowns (T.B.D) - Cinque Terra - Venice - Dolomites--Give or Take. Fly out Malpensa. Approx 3 night stays at each. I'm having trouble finding the right hilltowns to visit. I want to relax in 2 hilltowns, one in Umbria; one in Tuscany. NOT INTERSTED IN A MILLION DAY TRIPS from hilltown to hilltown. Maybe one or two at most. I just want to relax in/ get to know ONE beautiful hilltown in each region. Two that aren't super touristy, but that offer a lot of culture and cuisine. Could anyone recommend a hilltown in Umbria and Tuscany that we might love to relax in for 4 days each?

In Tuscany, I suggest staying in Pienza or Montepulciano. Or, stay here, only 3 km from Pienza-

http://www.fontebertusi.it/

In Umbria, I suggest either Spello or Gubbio. Here's a great hotel in Spello-

http://www.palazzobocci.com/

Hi C,

In Umbria, you might want to consider Orvieto.

In addition to being a lovely town, it has a really great restaurant - I sette Consoli.

See http://gram.eng.uci.edu/~alberto/orvieto/en_seeing.html

Sure, that is a fair request.

In Umbria, I agree with the Spello location and hotel. For Tuscany, it is hard to beat the location of www.palazzodelcapitano.com in San Quirico. There are several great food options within :20.
Have fun !

Another great place in Cinque Terre is the fantastic seaside town of Comogli again not touristy but a great town!

I second Montalcino! It was our favorite 'hilltop town' in Tuscany. Great for relaxing and there are few tourists at night. Volterra was our second favorite Hilltop Town.