Potential 2 wk Italy itinerary
 

Hi, all,

Thanks for the helpful suggestion so far re traveling with teens in Italy.

Here's our current (work in progress) itinerary. All comments and suggestions welcome.\

Day 1 Arrive in Rome, transfer to apartment
Day 2/3/4 Rome --- visit all the usual sights while un-jetlagging. Vatican catacombs?
Day 5 Train to Pompeii
Day 5/6/7 Pompeii/Herculean and countryside
Day 8 Drive to Orvieto or Urbino
Day 9 maybe Perugia chocolate factory
Day 10 drive to Padua
Day 11 cooking class, etc, in Padua and drive to Venice
Day 12/13/14 Venice

In Days 5 through 7 are you thinking of Naples, the Amalfi coast or Capri?

Pompeii, Vesuvius, the coast.

Which town do you prefer to stay in for days 5/6/7?

Question whether you need a car and for how long. All the places you mention are easily reached by train (except Urbino). Certainly, unless you have a specific need, I'd return the car in Padua as it's only a handicap while you are in Venice. Padua is only about half an hour by train from Venice.

Urbino is north of Perugia so if you want to there, consider going after Perugia.

Which coast? There is the Sorrentine Peninsula - or do you mean the Amalfi Coast?
There is no direct train to Pompeii - you need to go via Naples and change for the local commuter train to Pompeii. Where were you planning to stay around here? I don't recommend staying in Pompei itself when you have options such as Naples or Sorrento close by.
Take a browse through some guide books like Lonely Planet or DK Eyewitness and see what appeals - read up on the region as it will be helpful for you.