Italy for 2 weeks - Questions?

Yikes-- are you kidding? I don't think you will have much trouble finding great architecture everywhere you turn. Just walk down the streets is all you have to do. But do some research. The Duomo of course, I love the Medici town hall in Florence also, the Colliseum, St. Peter's in Rome, just about everywhere you turn in Greese, I imagine. It's architecture and great art in one.

It's often been said here that the problem with spending just one night in an area is that you'll spend so much of the day getting there. Some of your destinations are not near each other. Have you investigated how it will take you to get from Naples to Bari, for example? Maybe you should look at cheap flights between Naples or Rome and Greece Also, I'd advise eliminating at least one of the Italian destinations.

I'd also suggest eliminating one Italian destination. Personally I'd take out Cinque Terra as you are back tracking somewhat from Florence to there and then back to Rome. I also feel only spending 1 to 2 days in these areas is way too short. I'm sure you'll feel you've missed a lot. Also travelling to and from places takes time and can be tiring. There is so much to see and do in all the Italian towns you plan to visit don't spoil you're trip by rushing.

I think you're trying to see too much. I'd cut out out CT and Lake Como. The cities you want to visit need more than 1-2 day.

I would delete Lake Como before the CT.

CT is full of day-trippers during summer. It will be a hellish,tourist-laden place and is best avoided. We would recommend Varenna on Lake Como (be sure to enjoy a ferry ride while there). It is easily reached from Milan, which is NOT someplace you should waste your time).
For architecture and history, Rome is unparalleled .
Firenze ( Florence) is best viewed from Piazzale Michaelangelo, a park across the river from the main city, tho its streets have their charms.
How much time you can spend in each place depends on how much time you devote to Switz and Greece but keep in mind that the fewer places you go to and the more in depth your experience is in each place, generally speaking the more rewarding your memories are

Your itinerary sounds way too rushed. I just did 18 days solely in Italy, Rome was the longest stay (5 nights) and I wished I could have stayed longer.

I would cut the CT out of your trip, not worth the effort. I was there in mid-May and it was PACKED, June will be even worse. I might even cut Como.

Also Florence will be jam packed and hellish if there is some kind of festival so be prepared.

I went to Naples, I'd say to can skip it to give yourself more time in Rome or Venice.

Here's my take: Going to the Alps? Arrive day 1 (Geneva?), Plus 6 hrs to Alps. Day 2 for Jungfrau; 3 for towns and walks; 4, back-up for bad weather or go to Bern before Zurich night train. 5,6,7 Venice(don't skimp here, you'll be sorry). 8, early to Florence. Not into art? Fine, still see the David. Walk around a bit. Take a late or not so late train to Rome. 9,10,11(travel day) for Rome and 12,13,14 for Greece. Of course this is just a mock itinerary but it echos the sentiment expressed by the other "posters". Don't try to squeeze 3 weeks vacation into 2. What is "important to you", is what dictates your choices. My basic tips to you are: If your going to the Alps, your travel day out is your back-up day, if you don't need it you have a free day so have a plan for it. Great cities deserve time. 2 full days minimum. Don't count a noon arrival as day 1. Why 1/2 day Florence? Florence = Art. If you move too fast you will see more but experiance less. Just my opinion. Good luck.