Dear V.,
First deployments are so difficult! My heart goes out to you for all that you're going through. My husband was deployed right before Christmas last year. So I know how it is to have an empty place at the table during the holidays.
I suggest making a special DVD with everyone that your son loves and cares for. You don't have to get everyone together at one time, although Thanksgiving get-togethers are perfect! Just capture everyday moments so he can be part of life here at home. Everyone can send their love and well wishes. You can video tape a drive on a festively decorated street he knows. If you're sending him baked goods (ALWAYS a great idea!) have someone video tape you making them.
When putting together his care package, add some holiday decorations like a strand of lights, garland, bells and angels.
Don't forget some fun gifts he can enjoy as well as some practical things like hand/foot warmers, cocoa packets, marshmallows, a Christmas mug and lots of candy canes. Try including reading, crossword and puzzle books. Wrap up little gifts and stuff them in a stocking.
Send lots of pictures, too! He can carry small photo albums easily, so grab one from the Dollar Tree and load it full of pictures!
I always include hand written letters and art from my kids. My mother-in-law asked the children of his old elementary school to write to her son. They jumped at the chance to draw pictures and write notes to a soldier far away that used to go to their school. I recommend keeping his address private and simply collect the letters from the teachers. This is especially wonderful if you could ask that they write to any soldier. Your son can pass out the letters to all the men and women in his squad, platoon or company. Our service members really appreciate the effort and kindness such simple things bring. Really, it comes down to letting him know you miss him, love him, stand by him, and REMEMBER him.
Make sure you send it out within the first couple of days in December so he can get it in time!
God Bless you!