Before you consider sending a favorite food to a loved one, test it to see if it will survive the shipping and handling process. Place the food in a container and shake it a few times. If it holds its shape, it should mail well.
If you are sending delicate cookies like sugar cookies, you will need to prepare them as you ordinarily would and allow them to cool. Then, carefully wrap each cookie in plastic wrap and place them in layers in an airtight container.
For cookies that are not quite as crisp, you can crumble plastic on the bottom of the container, then layer the cookies and place a layer of crumbled plastic wrap between each layer.
If you are sending cakes, it is best to stick with those tried and true fruit-based cakes like fruitcakes, carrot cakes or spice cakes. Pound cake with a pour-on icing is also a good choice. Layer cakes simply do not travel well.
Most cakes and cookies can be easily shipped in metal cake boxes and canisters. Plastic containers also work well. To keep the goodies fresh, wrap the outside of the box in plastic wrap to seal it. It helps keep the cookies and cakes from drying out. Then, place your package into a cardboard box for mailing.
Place a cushion of crumbled newspaper, paper towels, styrofoam pellets or unsalted air-popped popcorn in the box and then add the containers of food. Finish packing the box with paper. Securely close the box, seal it and mark the box perishable and fragile.
If you are sending food to your friends during the holidays, it is best to call ahead and make sure they are on the lookout for the package. People are often reluctant to open boxes they do not expect or if the box is delivered to a different door than they expect. The boxes could sit unattended for days before anyone knows they are there.