So I will be spending almost 2 weeks in italy and the person I am going with is a Europe travel "rookie" (I have been to italy 2x before - Rome, Cinque Terre, couple of other smaller places)...
So I am thinking of going to Rome (thats where we are landing/departing from, Florence, Pompeii, and maybe see a bit of southwest coast (close to Capri, Amalfi) while visiting Pompeii... What do you guys think?
Also do you have any suggestions on how long to stay in Florence, etc...
Thank you all in advance for any advice!

A couple of days in Florence would be nice. Have you given any thought to getting out of the city and looking at the Italian countryside in Tuscany for a few days??? I think you'd enjoy it.

When are you going?
What is your budget range?
What are your interests?

If you have not been to Florence and Venice, I would definitely consider those. They are by far my favorite places in Italy.

Chicago_Heather,
We are going in mid June
Budget Range is about $3K for the travel itself (paying $2k for tickets)
Also pompeii is a must see because my friend and I both want to visit it...
As fas as our interests, archeology, art, nature, wine, and good food ... Also we are in our mid-20s if that helps any... Thank you all!

I highly recommend the Amalfi coast, especially since you will be so close. Tuscany and Venice are a "must see" too. That's why we took a month to visit Italy.

redstar92... you've been twice, and I know you'll be back, so I stay stick with your original plan.

How about landing in Rome and going straight to Florence for a few days?

You could then train to Naples from Florence, stay a few nights in Sorrento and see Pompeii, and maybe even spend another few nights on Capri or in Positano.

Then, back to Rome for a few days before heading home.

How long do you have for your trip? That could help with deciding how long to stay in each place.

Oh, what an idiot I am. I just saw the "2 weeks in Italy" subject after I posted. Ok, let's assume you have 14 nights:

Land in Rome and spend nights
1 through 4 in Florence, with a day trip or two out of the city.

5 and 6 in Sorrento with trip to Pompeii.

7 through 10 in Positano or on Capri.

11 through 13 or 14 in Rome.

If anything, I would add time on the Sorrento, Pompeii, Capri and Amalfi Coast portion.