When your sailor gets shipped off to the airport, to leave for basic training, he will most likely be allowed his overnight bag that he had with him at the hotel the night before. In boot camp, he is allowed pretty much nothing. I would suggest sending your loved one off with a picture of yourself. I know you will want to give him a big stack of pictures, maybe of his friends, family and of course, about 20 of you & him, but those are best left to be sent in future letters. Once he gets to boot camp, as I said, everything, including his wallet and anything else on him, will be taken from him and put in a box, and subsequently mailed back home. So, it would only make sense that he carry the single picture of you, just to have while he travels to boot camp that first day. Those first hours away from each other will be the hardest! So, that picture will be a great comfort, if not the only comfort to him during those grueling first hours.
A little hint though, they do allow him to carry a bible. Inside the jacket of the bible, write down yours and his mother's address, so he won't forget, and then a wee note telling him you love him. You don't want him forgetting your address, because you won't be able to write to him until he sends you a letter with his Rank/number and address.
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