why dont you just leave it as an italy trip? it appears there is a chabad in naples for shabbos. thats what i would do if i were you. leave zurich for a different time. i certainly wouldnt sacrifice a day in capri etc for a day in zurich
We ended up with the following itinerary:
Arrive Thursday afternoon
Venice Thursday afternoon-Shabbos
Train to Rome Sunday morning
Rome Sunday afternoon-Tuesday afternoon
Driving through Tuscany Tuesday afternoon-Thursday afternoon
Florence Thursday night
Zurich/Lucerne Friday-Monday
Leave Monday
The reason we ended up planning on going to Zurich is because my wife has family there. I guess we'll have to save southern Italy for another trip.
Also we were recommended by frequent Italy visitors that driving though Tuscany would be a lot less crowded at the beginning of July that Naples, Pompeii, Capri, etc would be.
Anyone drive through Tuscany? How was?