My wife and I are taking two of our sons (ages 24 and 21) for their first ever trip to Italy. I have been to Italy three times and my wife has been once (she has been to Venice, Florence, Rome and in addition I have been to Milan, Lake Como, Sorrento and Amalfi Coast). Our sons like antiquities and outdoor activities and would like a smattering of art. We would probably skip the Uffizi but go to the Accademia with them if that give you any ideas. We have flights arranged to fly direct from Charlotte to Rome (arrive at 9:45 AM on May 8) and depart from Venice (May 18 at 11:30 AM direct to Philadelphia connecting back to Charlotte). This gives us 10 nights. We plan to spend three nights in Rome and then head to Tuscany/Umbria and the Cinque Terre. We have the final three nights planned for Venice (could cut this to two nights). The question is - how do we do the middle of the trip and in which order? We would have 4-5 nights. We want to have a base in Tuscany (maybe Siena?) and do a day trip to Florence as well as some other hill towns. Should I plan to rent a car for this portion or is there enough public transportation for us to get around efficiently? Also I think we would want to spend two nights in the CT and maybe do a stop in Pisa between locations. Any recommendations for a base/lodging? Which is the better itinerary from a train schedule perspective?
Rome > Tuscany > CT > Venice OR Rome > CT > Tuscany > Venice
Any tips and recommendations will be greatly appreciated!