Hi,
I'm looking for some general advice. My husband and I are planning a trip to Italy for our anniversary leaving in mid to late October to early November for about 10 to 14 days. I would like to pick an interesting medium sized town that will take 2 to 4 days to see well, offer good restaurant choices in the evening and be reasonably central for day trips by train preferably. The other option would be two or three such places, but I would rather not have to pack and unpack. Last year we spent 3 days in Orvieto before a cruise and it was perfect. I have considered Venice, but am a bit concerned about rain and flooding that time of year since what really enjoy is just walking around. Maybe Bologna? Sienna? Any ideas?

I think Bologna has everything you are seeking. A number f train lines cross there, so you can make interesting daytrips in all directions-- Ravenna, Ferrara, Rimini, Modena, Parma . . . Many would say tha Bologna is the culinary capital of Italy.

I also like Verona for the same reasons. It is also a transit hub, so daytrips include Vicenza, Padua, Lake Garda, Venice, and even the Dolomites. The city is known for its wine bars--and main courses featuring horse!

Both Bologna and Verona have interesting sightseeing as well.

Good question !
Let me offer 3 good options in rank order:
Lucca---good day trips and very good food options
Siena---a true medieval treasure but a ton of tour busses.
Verona---Lovely city and good day trip to Lago Garda

All 3 have good train connections. Have fun !

Perugia! Easy train and bus travel through much of Umbria and parts of Tuscany.

I think I'd pick Perugia as well.

Dear Joannecam,

come to enjoy Bologna!!!!