the biggest problem now is the 50 lb limit. 11 bottles plus a light suitcase barely gets under 50 lbs. if he with partner/spouse, can carry 44 bottles.

does italy have the no liquid laws in force for flights to usa? otherwise, he could also stash 6 bottles in his carryon, as long as it is nonstop.

duty in us, which is neglegable, is usually not collected. transport of wine in the hold is allowed in usa. or if it is illegal, i have not been witness to enforcement.