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Flight questions East Coast to Italy

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Trying to figure out the best way for my family of 4 (including a 4 and 6 year old) to get to Italy. At this point, Rome/Venice/Milan are all possibilities. We will be in Italy for almost a month. We initially planned to leave out to Boston. Questions:
1. The appears to be just TWO nonstop flights from BOS to anywhere in Italy, both going to Rome. They are pretty spendy. How valuable is a nonstop? Valuable enough that it would be smart to fly out of JFK and deal with the initial hassle of getting to NY? The nonstops from JFK appear to be about 35% cheaper for the dates we are going.
2. If nonstops don't turn out to be within our budget, it is easier in your opinion to fly and transfer in Europe, or fly to a another domestic airport (say from BOS to Philly) and then nonstop to Venice?
Trying to limit the amount of headaches with missed connections/luggage/hauling little people through the airport...

Thanks,
franchesca

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