I have a bunch of friends overseas right now, so I've been putting together a few care packages lately. Some guidelines I like to follow:
Just like emails, care packages work best if they are smaller, but arrive more frequently. The fact that you get something is the best part, not that it's perfect.
Remember these are items that need to keep well, and be eaten on the move, and may well get very hot and very cold on the way.
The process takes a lot of steps, which is why it is hard to complete sometimes. (I had some friends tell me after I got back last June that they had put a package together for me, then never gotten around to mailing it, and eventually started eating it as sat on their kitchen counter. It made me laugh because I have done that myself.) They are: get a mailing address. Buy the stuff. Pack the box. Take it to post office to mail. (You have to do this because it is going overseas, and you have to fill out a customs form).
So, what I usually do is the the address from an email they sent, put it on a post note, and stick that note on the box I intend to use. Once again, the box doesn't need to be huge. 10" X 13" X 5" is a good size. Then I go and buy things at the store and repack them in the box, which I throw in the car and mail the next time I can.
Items I like to include:
A note. ANY news from not-in-the-desert is entertaining!
Triscuits (or other crackers like Ritz, Saltines, etc. Buy the small box and leave the crackers in it.)
Easy cheese. (One can per box of crackers.)
Summer sausage. (Nice because it comes sealed in plastic, and keeps well. Also, after you open it, you can slice easily, and put on the crackers, but it isn't as messy as tuna or (shudder) Spam.)
Chocolate. I like the fun sizes of Snickers, Butterfingers, Baby Ruth, etc. I buy the big bags and then repack them in 1 quart ziploc bags. This makes them a little easier to carry and share, and also contains liquid chocolate if the package gets hot on the way. Also the ziploc bag is often useful afterwards.
Drink mix. Obviously it is difficult (though not impossible) to mail liquids. Unless someone is really jonesing for a particular beverage they can't get downrange, get the drink mix instead.
(See note on alcohol below.) I also takes these out of the original box and put in mini ziploc bags.
Cookies. I buy the variety packs of small (~2 oz) bags of things like Cheeze its, Animal Crackers, frosted animal crackers, mini oreos, mini chocolate chip cookies, Nilla Wafers, etc. The small bags let you avoid repacking them yourself. I open the box and put the small bags in the care package loose, they also act nicely as padding.
Other candy. Fruit roll ups, gummi bears, twizzlers, etc. Again I look for small bags, or I rebag them myself.
Beef jerky.
Trail mix.
Other stuff: Current magazines, books, small cheap toys like legos or suction cup dart guns or matchbox cars.
Illegal items:
Booze
Porno (Note that the CENTCOM version of porno means "any depiction of a female body above the ankles, between the wrists, and below the neck." Not kidding.)
Bibles or other religious materials.
(For those of you who speak military, possession of these items will generally get a military member an at least an Article 15 off the bat, no questions asked. For those of you that don't, that's
bad.)
Once you get into a decent rhythm, you can start customizing based on inputs from them, but don't stall out on the process, or you'll never get them mailed. If you don't hear from whoever, just mail it generic. Oh, and if they have their address before they leave, pack one and mail it the same day they do so they will get it a couple of weeks after they arrive.
Oh, also: Do yourself and the person you are mailing it to a favor: Don't use their rank in the address, and leave as little return address information as possible (magazine mailing labels, for example). Anyone downrange should be shredding or burning address information from inbound mail, but make their job easier - don't write it on the box, use a label they can easily cut off. If a bad guy (or opportunist) sees a rank on a package, they might decide it's someone worth mailing a letter bomb or poison fruitcake to. Or maybe they'll mail it to the return address.