Venice or Orvieto?

There's no place in the world like Venice. 7 days in Florence...way too many for my taste.

I've spent 2 nights in Orvieto, and have seen EVERYTHING there. It's a lovely place, but unless you have a car to drive around the countryside to visit wineries, there isn't 3 days worth of stuff to see.

I have spent a total of 5 nights in Venice, and I still have a long list of things I'd like to see and do there.

No question: Venezia! Angela nailed it. We've spent 24 nights in Venezia over the years and will go back in December for our annual fix.

So you have 2 weeks. I like to count nights on the ground. So let's assume it's 13 nights. A good rule of thumb is to spend at least 2 nights at the same hotel so that you don't waste too much time checking in and out of hotels.
It's your first time in Italy, and Rome, Florence and Venice are the first timer must dos.
So I would spend:
3 nights in Venice
4 nights in Florence (with a day trip or two within Tuscany)
2 nights at the Cinque Terre
4 nights in Rome (you can take a day trip to orvieto from Rome if you wish, it's only 1hr10min away by train).

If you can find an open jaw multi city flight, with arrival to VCE and return from FCO (Rome airport code is FCO) that would be ideal

Absolutely - Venice! Our second trip to Italy was planned around an itinerary to return to Venice for 3 more days; it's that special!

If it's your first trip to Italy, I would recommend less days in Florence and possibly add Verona. Verona is lovely, and it's an easy town to enjoy. Here's some train info:

Florence-to-Verona: 1.5 hours by train (you don't need to switch trains)
Verona-to-Venice: 1.25 hours by train. Make sure you go to the Venezia Santa Lucia stop (not Mestre) and select a hotel on the islands vs. the mainland.

I'm with the others. Venice to start for 2 or 3 nights, and take 2 days off Florence and add one more town. My suggestions: Verona or Bologna before Florence or Orvieto after Florence.

Florence is all about Renaissance art and architecture. If you really enjoy it, 3 days is a minimum to see it. Then add day trips to Siena and either Lucca or San Gimignano, that's 5 days. One more for an organized wine tour?

I could spend weeks in Florence, so six or seven nights (with some daytrips to wineries, other cities in Tuscany) doesn't seem too many to me.

I love Orvieto, too, but for a first trip to Italy it is fine as a daytrip (try to be there late afternoon when the lowering sun hits the Cathedral façade).

If you can arrange to fly into Venice (or Milano and take the fast train to Venice), it will save you some backtracking from Florence, but I would definitely put Venice into the itinerary for the 3 days/nights you are trying to fill.

If its your first trip to Italy I'd definitely go to Venice! :)

Chani and Jean make good suggestions for Verona and Bologna. If you like eating you cannot beat Bologna and it does not feel overrun with tourists (in contrast to Orvieto).