I made a few of his favorite kinds of cookies on different days (chocolate chip cookies with walnuts, sugar cookies and snickerdoodles) and once they cooled I packaged them in separate disposable food containers and wrapped each layer of cookies in plastic wrap and then froze the containers of cookies.
It is important to make sure the containers you are using will fit in the flat rate boxes, which are the best boxes to use to ship overseas. I use the Large Flat Rate boxes which can either be picked up at the post office, or ordered online (for free). Other size flat rate boxes are available, but I generally use the large size so I can send the most amount of cookies at once! You will also need to fill out a customs form listing each item in the box, and you can pick up or order those and envelopes for them for free too. You can also fill out the form online while making a shipping label and print it yourself. I find this to be the easiest, as it lets me do all the work at home instead of having to go to the post office and wait in line. As an added incentive, it costs about $2 less per box if you print the shipping label and customs form yourself. To do this, simply make an account and use Click-N-Ship. The large boxes cost me $13.80 to ship overseas this way ($15.80 to ship within the US).
Now that you have your box and cookies, it's time to package them. It is best to use bubble wrap to make sure the cookies don't slide around too much and break. The containers I used would not fit stacked in the box, but I also didn't want to leave too much empty space, so I took some of my cookies out of the container (still wrapped in plastic wrap) and put them in a Ziploc bag, and placed that on top of the container that was already in the box. I like to keep everything frozen as long as possible, so I packaged the box up and put it back in the freezer, and then brought it to work with me the next morning for the mail man to pick up. You can also schedule a pick up at your house.
This box took 9 days to get to my husband. Luckily, he said the cookies tasted great when they got there, so now I need to bake some more for him! I would imagine that homemade cookies are one of the best items someone can receive in a care package when they are thousands of miles away from home. I know for my husband, it was the box he had been looking forward to the most.
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