re: Two weeks in Italy. Tell me pros/cons of what I am thinking already...

I would do a day less in Rome and Florence, rent a car and see Pisa, Sienna, Montalcino, San Gimignano. Then a day in Umbria. Assisi and Perugia along with a few hill towns are fantastic.

I would skip Naples! Take the train into Salerno from Rome and have driver scheduled to pick you up. You can use the local SITA bus to see Amalfi, Ravello, Sorrento and take the hydrofoil to Capri. From Sorrento you can take the local trail (Circumvesuviano) to the Pompeii Scavi exit. Enjoy!

You can also take the return train to Rome from Salerno!