Your Favorite Towns in Tuscany and Umbria

A huge yes to Orvieto, Lucca and Siena. There probably isn't a "bad" town to visit. The Basilica at Orvieto is not to be missed, as is the gelato shop to it's left side.

I would include Volterra,San Gim,Cortona and Civita to the above post.
Mike

Will you be in Spoleto in mid-July for the 2 Mondi festival? If so, more details will follow, or send me a PM.

Spello, Trevi, Todi, Cortona,in addition to those already mentioned. Google "images" for all these cities, you will see how beautiful they are.

we stayed in cortona and San G. we visited volterra. they were all good.( volterra was not as nice, if I had to rate them) but the real experience was gained by staying in them. when the day trippers have gone, the locals come out. In San G in the very late afternoon I happened upon, what looked like, the local group practicing their flag tossing routine. ( just like on the movie, under the tuscan sun) there was virtually no other people around to see them. it was great to see local people enjoying themselves. also waking up early to see the hot air balloons climbing up from the valleys below. you only get this by staying in the town.
hope you have a great time.

Spello and Spoleto in Umbria! So genuine and (relatively) lightly touristed.

I am not a fan of San Gimignano. It felt fake to me. Volterra is more real, more historical, IMO. Lucca is fabulous. Civita' di Bagnoregio is interesting to see, a good place for lunch, but if it is way out of your way, I would not spend too much time. Not worth spending a whole day of your precious trip.

I'll be taking at least one day trip by car from our hotel in Montecatini Terme to some of these towns, so thanks for posting! Helping me decide as well, I might just start driving and randomly visit spots!

Dantbarnes, with a car, that is my favorite thing to do - see something in the distance and just drive toward it. If I'm on a bus or train, I make a note of the place we are passing and try to work it into my schedule. So much easier with a car!

I like some small towns with basically locals and minimal tourists to see a different side of Italy. Citta Della Pieve in Umbria is one I like.

I'm not much help because I loved every town in Tuscany that I visited. If forced to make choices I would say Volterra, Lucca, Cortona (in that order) were probably my favorites, after Florence and Siena of course.