We are heading to Italy in May and have been several times. We have done what I would consider a broad swath of hill towns (well known and otherwise) including: Orvieto, Pienza, Lucca (loved it), San G, Montalcino, Montireggioni, Radda and Montepulciano (and the other biggies). We are renting a villa in Cortona with friends and I am interested in some day trips to lesser towns which are interesting from an architectural/scenic perspective (and can be hill towns or just cute small towns) and of course FOOD!! The towns I'm thinking of include: Gubbio, Deruta, Montefalco, Urbania, Perugia, Spello, Bevagna, Todi, Volpaia, Bucine, Anghiari, San Casicano dei Bagni and Civtella val di Chiana (apologies for some butchered spelling I'm sure). I'm finding it difficult to find a good resource or advice on the web as to which would truly be interesting to visit and which are just a list on a website. I only want to do about 1/3 of my list so appreciate any thoughts on the "best" of these or others and/or a great resource book on the small towns which gives recommendations rather than just a list. Thanks for the assist.
First of all, I recommend you get the Cadogan Guide which combines Tuscany and Umbria. We like the Cadogans precisely because they cover, in detail, many of the small places ignored by other publishers. We've been to several of the places on your list; and for what it's worth, here are my opinions. Deruta is about one thing - - ceramics. If you want to buy - - and they are beautiful and well-priced - - go; otherwise skip it. I always stop there when Í'm in the area. Montefalco, Spello, and Bevagna are small and near each other. One day should suffice for all three. Perugia is more of a small city than town, with a cathedral, art museum, nice main piazza, chocolate factory, lots of shops, restaurants, etc. Definitely worth a day. We liked Gubbio, which we combined with a drive to Urbino, which we liked even more (lots of driving for a single day). If you like art, Arezzo and Sansepolcro have wonderful examples of the works of Piero della Francesco. Spoleto is interesting for its cathedral and 14th century viaduct. We haven't been there, but Panzano is famous in foodie circles. Buon viaggio,
This is a comprehensive guide to Tuscany's towns and villages: http://www.borghiditoscana.net/ For Umbria you can see this resource:
http://www.bellaumbria.net/en/itinerary/ This is a guide to Italy most beautiful but less explored villages, just click on the region and the village you want info on: http://www.borghitalia.it/index_en.php All of the towns you are in your list are featured in the above websites. I don't want to tell you what I would do, since there are so many places to visit in the area and a lifetime wouldn't be enough. Just search on the resources I gave you above and make your best decision. In making the decision consider the distance from Cortona. For example I wouldn't visit villages in Maremma (Southern Tuscany) or you'll be driving most of the day to get there. Using google maps see what is within 1 to 2 hrs drive from Cortona (which is already a lot).