Any thing I've sent APO usually gets there in less than 3 weeks. Month max...

A good ziploc bag should work fine, but the tupperware container is an even better idea because he can use it as a makeshift humidor over there. Then just make sure you pad the crap out of the cigars so they don't get jumbled around in the box (use the free USPS Priority Mail boxes with bubble wrap or styrofoam peanuts).

Please PM me an addy for him if you would, I'd like to put together a little package for him as well... I've got some CAO's and other goodies I can part with...