I've had a horrible time sleeping on flights from the east coast US to Italy. Something about the anticipation keeping my brain buzzing.
The first time was the worst, while also being wonderful in a few ways, as I pretty much like flying. Our plane that we took from Los Angeles arrived very late at JFK and we missed the connection after running down the airport byways. Big clump of harried passengers in front of the desk, much agita'. We got sent to Milan, and our luggage failed to transfer, so it arrived in Rome, our destination, without us. We got to Milan (another story, my passport was expired!) and had a five hour wait to catch an Alitalia flight to Rome. Couldn't sleep in the Malpensa airport either. Got to Rome with a train from Fiumicino airport and then to our hotel area by subway, followed by walking down a main street (cobblestone sidewalks) with a month's worth of luggage, and then uphill to the albergo. We tossed our suitcases and went down to that big street and had our first food in Italy. I forget what I ordered, but remember what the people next to us ate - a very large bowl of piping hot spaghetti to which they added a hefty amount of parmigiano and unbelievable amount of butter...
and then we went back to the albergo and sleep.
That was 36 hours awake (that includes getting up and out our front door in Los Angeles and waiting for that first flight..)