I will be traveling with my wife and 2 kids (ages will be 7 and 12). We are sharing a villa with a couple of other families for a full week about 40 minutes outside of Florence near a town called Cerbaia. While we are at this villa, I plan to have a rental car to do some day trips. Thinking Siena, San Gimignano, Pisa/Lucca for the day trips. But I have also read that Montelpuciano, Volterra and Pienza are worthwhile, so I could try to add or substitute these in.
Aside from this week at the villa, I would like to fly in a few days early to adjust to the time difference. A cursory search of flights looks like it might be too difficult to fly into Florence on United Airlines (this is who i accrue my miles with). So I might have to look into Milan, Venice or maybe Genoa. Then rent a car there to drive to the villa. Any suggestions on which city to fly into and spend a few days?
After the week at the villa, we would also like to spend another 6 or 7 days on our own exploring a bit more before flying home, either from the same airport, or a different one. I think I would prefer to leave Rome and vicinity for a different trip since I am sure it will be miserably hot in mid/late August. (but tell me if you disagree).
Instead I was considering heading to the Cinque Terra for a few days (I know a hotel in Monterosso which has parking), and then from there? Head up to Milan for a couple of days with a day trip Lake Como before flying home?
I am trying to be aware of and follow my own advice of not trying to cram too much into a small window of time anywhere. Just wondering what others' thoughts are on a general itinerary.