While you are in Naples have lunch or dinner at a restaurant near the Egg castle named Antonio Antonio. It has a beautiful view of the bay of Naples and you can sit outside. I would also reccommend Capri. You can take a ferry from Naples. The Blue Grotto is a very romantic and interesting thing to do while in Capri. If you have a couple days in Naples I would also suggest the Amalfi Coast. Very beautiful and romantic. You can either drive the Amalfi Coast and hit some of the really nice towns like Ravello or Positano, or you can take a ferry ride and see it from the water. Pompeii is really really big. Probably bigger than you would think. If you really want to look around at everything there it would take you all day. If you were interested, you can also climb to the top of Mt Vesuvius.
Venice is my favorite place in Italy. Very unique. Definitely go on a gondola ride. They usually run about 50euro per person.
While in Rome take advantage of the metro system!!! It is VERY easy to use. It only has 2 lines: the red line and blue line. Both cross at the main train station (Termini Station). It is very cheap and will save you a lot of walking time since Rome is so huge. If you get off at the Trevi Fountian station (Barbarosa is the name of the stop) and turn left up the street you will find a Church called the Church of the Immaculate. It has a crypt in there that has 5 rooms that are completely decorated with human bones. There are over 4000 bodies that make up these rooms. It sounds really weird, but you'll never see anything else like it. The chandiliers and everything are made of bones.
Also, while in Florence you can take an hour train ride that will cost less than 10 euro and go to Pisa so you can see the Leaning Tower. Also while in Florence, visit Piazzale Michelangelo. It has a beautiful view of Florence and the surrounding Tuscan countryside.
It sounds like you are going to hit all the good places to see in Italy. Believe me, the 2 weeks will fly by. Have fun!
Live in Italy for 2 years now