I'm not familiar with the way skip works.
I'm in nj and I don't know if Italy makes it to the west coast, garrenttyes Geancarlo's signal will pass through nj on it's way west.
Giancarlo was my first and only European contact on AM.
From October to March is a good time, the end of October the bands are singing. You need to do it ideally when both of you are in daylight.
This is an excellent site for working out whether you stand a chance on a particular day and it'll give you a percentage chance based on time of day.
http://www.voacap.com/prediction.html
Propogation is as important to learn about as antennas when it comes to working DX.