Our Trip is in July - we're teachers - and traveling with our 15 yr old son. Flight is booked in and out of Rome. Since we need triple rooms, I like to plan and reserve all lodging ahead of time. We prefer family owned B&B type with communal breakfast/spaces to relax in the evening over wine and conversation with fellow travelers, hosts. I thought to head south first, thinking weather may be better there early July than later. Train tickets will be bought 120 days in advance for savings. Here is what I've worked out so far as an itinerary.
Day 1 - Arrive Rome : due to late hour, taxi straight to hotel (Grifo 2 nights)
Day 2 - Vatican/Sistine/something not covered by roma pass (we have 3 more nights in Rome at end of trip)
Day 3 - 9:00 train to Naples - check baggage at station(?) and see Archeology Museum, eat pizza, and cover some of RS Naples walk, then on to Sorrento.
3 nights in Sorrento (Il Nido? or something closer in town?)
Day 4 - Pompei/Herculaneum/Vesuvius
Day 5 - Paestum
Day 6 through 19 - Here is where I need some itinerary advice
Day6 - Train to Orvieto - Pick up rental car for 7-10 days Umbria/Tuscany - would like to stay at a few well positioned agriturismos and take day trips
Florence/Sienna - would rather see these without the car, so may plan 2-4 nights for them by train before or after car rental
Pisa? Lucca?
Is there time for a lake? - with or without car?
Milan? - We would like to see the Last Supper - but have no wish to stay in and would rather avoid Expo crowds
?Where to drop the car
Day19 - Train to Venice - 4 nights Pens. Guerrato.
20 - Venice
21 - Venice
22 - Venice
Day23. Train to Rome - 3 nights Maison Giulia.
24 - Rome
25 - Rome
Day26. Fly home (AM flight)