After much deliberation on a new itinerary (after you guys told me I was too aggressive on the last one - which I agree), I have come up with the following ... (remember I fly into either Milan or Rome on standby with Continental air, there is no negotiating on a free flight). Let me mention that it's possible we arrive in either Milan or Rome, but we will almost 100% be leaving from Milan to go back to the USA (based on flight loads):
Landing in MXP (Milano):
Day 1 - Arrive Milan 8 AM, transfer via train to Venice (arrive 3:30ish)
Day 2 - Venice
Day 3 - Venice until 1:00ish, transfer via air to Naples (3:10-4:30), Sorrento to sleep
Day 4 - Amalfi Coast
Day 5 - Amalfi Coast early, Pompeii on the way to Rome
Day 6 - Rome
Day 7 - Rome
Day 8 - Rome to Tuscany (train, not sure where to get off and rent a car, maybe Orvieto?), sleep Tuscany
Day 9 - Tuscany
Day 10 - Florence (via Tuscany train, sleep Tuscany still)
Day 11 - Florence and/or Tuscany
Day 12 - Cinque Terre
Day 13 - Cinque Terre - transfer to Milan in evening, sleep Milan
Day 14 - Milan to USA
Landing in FCO (Roma):
Day 1 - Arrive Rome 8 AMish, Rome
Day 2 - Rome
Day 3 - Rome
Day 4 - Pompeii, Arrive Sorrento, Sleep Sorrento
Day 5 - Amalfi Coast
Day 6 - Amalfi Coast/Sorrento, Flight from Naples 5:00-6:15ish to Venice
Day 7 - Venice
Day 8 - Venice, early transfer Florence, Florence
Day 9 - Florence
Day 10 - Tuscany
Day 11 - Tuscany
Day 12 - Transfer Cinque Terre
Day 13 - Cinque Terre - transfer Milano in evening, sleep Milano
Day 14 - Milano to USA
What do you guys think off either plan? Any suggestions? What might be the best way to rent a car in Tuscany coming from Rome, coming from Florence?
Thanks again - Brian