Itinerary for 14 nights in Italy..is it still too much?

I'd still say drop Bologna and add it somwhere else. I've seen only a portion of Bologna and it's nice but after seeing Rome, Florence and Venice it's not gonna seem all that special. Myself I'd add to Venice.

Unless you are using San Gim as a base to tour Tuscany countryside, I would say, limit yourself to 2 days and add a day to Venice. I did a side trip vineyard tour to San Gim from Siena and found that 3 hours in San Gim was adequate. We spent 3 days in Venice and used every bit of that time there, exploring the nooks and crannies of Venice. You could also add that day to Rome, but if you ask me, Venice kicks Romes butt. I wouldn't have to return to Rome, but I would visit Venice over and over. I recently did Milan 1, Florence 3, Siena 2, Assisi 2, Rome 4, Venice 3 and found that specific time perfect for each city. I did not miss anything I wanted to see and experience it at a pace that was very comfortable. But of all the countries I have visited in Europe, Italy is by far the most exhausting because it does offer so much. In my opinion, there are just too many 2 nights stays in your plan. If you skipped Bologna you could add those days to Florence and Rome or even an extra one in CT but I know you are loving Bologna right now and have your heart set on it.

Hi guys, Thank you for your feedback. It's very much appreciated once again. My husband and I are big foodies and not so much into museums and stuff like that. I know sad to say. I don't mind them but not a priority. I mean I want to see the Colosseum, Trevi, Pantheon, Spanish Steps, etc.. but this trip will be mainly for food and the squares where we can sit around and have more food and enjoy a bit of the culture. I just want to give you guys a bit of my reasoning as to why I picked those places. San Gimignano was suggested to me by a friend....which I'm changing...we will stay there only two nights instead of three. I think I'll add that third night to Florence instead. Anyways, I thought since we will have a car there it would be easy to explore the town for a couple hours then drive around to see Chianti and Siena..maybe Volterra. I'm counting this all in while we are there and taking our time driving into Florence. And yes, I do have my heart set on Bologna....pasta, mortadella, etc...I know there's not much there but they keep talking about the food!!:) So this is why I chose these places.... After all the responses I've gotten...it seems like there will be never enough time to see one place no matter how much time we spend. So now I'm thinking since this is our first time visiting Italy...I feel like we'll get a taste of a few places. And hopefully get a sense of which places we like the best so then for our future visits we'll know exactly where to go. And I already cut out Sorrento because of you guys!!:) So I know the Amalfi coast we'll be on another visit. Thank you all again again for you help, tips, advice, everything. It is very much appreciated. Thank you,
Jaks

Jaks, if you and hubby are foodies (as my hubby and I are) are you going to make a stop in Panzano while you are in Chianti/Tuscany? A stop at Dario's is a must, if for no other reason than to buy his "perfumo" the amazing salt and herb blend!
If you haven't already chosen your restaurants let me know and I will give you our recs.

Hi ekc, We haven't picked any restaurants yet and of course we are open to suggestions so any that you have please send them out!!:) We are staying in San Gimignano for two nights but have a car and from what I hear, San Gimignano is small...so we will use it as our little base to go venture around to Chianti and whatever other wonderful place we happen to discover. Thanks again, Jaks