I mail cookie's all the time. I individually wrap each one. Then wrap them with tissue paper. I use the boxes from the post office that are $4.95 to ship. You can get 8 cookies in the box and the box will fit into people's mail box.
I ship a great deal and have found it is imperative that you put the cookies in the box stacked vertically. I wrap each one (already in individual cello bags) with the small bubble wrap. I then put a good amount of peanuts on the bottom of my box. I stack the cookies vertically side-by-side snugly, then surround with peanuts on all four sides and top with more peanuts. If you can shake it and have movement, you need to add more peanuts. I then make tags to go on the box that say "VERY FRAGILE", then on the next line "Top Load Only. Thanks!" I also bring cookies to my UPS guys each time I have a box to send and I don't think that hurts.
When I send USPS I cross my fingers as I have seen my boxes being tossed into the outgoing bin, even after nicely explaining that they are fragile, breakable cookies. Even with that, I have not (knock on wood) had any breakage if I pack them this way. For small cookies where I do not have many (cookies for niece and nephews), I have used the very small Priority Mail boxes (the size that would fit a VHS tape). That is the same size that CreativeCookiesCakes is talking about. I wrap each cookie individually with bubble wrap and then insert. You want it to be tight, but not overdone with a bit of peanuts if you can on the top, bottom and sides. I have been fine the few times I did not have room for the peanuts, but placed small bubble wrap in place of the peanuts. I have sometimes had problems with the skinner, rectangular Priority Mail boxes as the tendency is for weight to be placed in the middle of the box and thus snapping cookies. If I need to use that size now, I place the cookies first in another box (decorative strong ones I use) with bubble wrap on the bottom, top and sides of that little box. I insert the decorative box into the larger PM box with peanuts on all four sides. I have had success with that. I have had very good results with the deeper largest size PM boxes, again stacking them vertically with peanuts on top or bottom. You do not need to use PM boxes, but the idea that I have found is that unless it is the small, small size where the tendency would not be for weight to be placed directly in the middle, you need to use a box with some depth, surround with peanuts and stack the cookies vertically. With any USPS boxes I send out, I stamp the outside of the box repeatedly with their "FRAGILE" stamp. That is just what has worked for me.
One important thing is to watch your design. You do not want anything with points or tall parts that can break off.
I recently shipped cookies by USPS. Larger outer box with decorative box inside. I used the "air packs" between the inner and outer box so that there was no movement of the inner box. I packaged each cookie individually with bubble wrap in the bottom of the inner box and bubble wrap between each layer of cookies and also between the cookies and sides and top of the box. Nothing was broken, but I did not send any cookies with points or parts that could easily break off. Hope this helps!
i ship cookies all the time, too. To family and friends, though - not orders. I rarely have any breakage (according to the recipients, that is). I'll post pictures to go with each step in my photos for a visual aide. http://cakecentral.com/modules.php?name=gallery&file=displayimage&pid=1719773
Here's what I do....
Packing for shipping materials
1. plastic bags: I recycle plastic bags from the drycleaners or the grocery store as packing material
2. plastic container: I use the plastic containers from the salad bar at the grocery store as a container when shipping cookies.
3. priority mail box: I like the medium size priority mail box form USPS. Its the perfect size for the plastic salad bar containers at my local grocery store.
Packing for shipping my method
1. Open plastic salad bar container and line bottom with slightly fluffed (crushed up) plastic bags (see picture 1). I usually do 2 or 3 layers, depending on the size of the bags.
2. Layer cookies in, fitting them as close together as possible to avoid much movement when shipping. (see picture 2).
3. Continue layering cookies in the box with a layer of fluffed plastic bags between each layer. If the cookies are very fragile (like martini glasses), I also put a thin sheet of cardboard under each layer of cookie to help keep it flat. I try not to do more than 4 layers in each box. (see picture 3; note: these cookies happened to be really big, so I couldnt fit more than 4 in each layer of the box, but other cookies I can usually fit about 6 per layer)
4. When you have 3 or 4 layers of cookies, fill in the space in the plastic box with additional plastic bags as cushioning. Try to put enough cushioning in so that the cookies dont have much room for movement, but not too tight that the pressure will break them. (see picture 4)
5. Close the box. Place the plastic box filled with cookies in the priority mail box, using additional plastic bags as cushioning around edges and on top and bottom of the plastic box. (see picture 5; note: this is the large size box, not the medium that I usually use because I ran out of that size)
6. Seal box and get ready to mail. I write fragile and perishable on outside of the box in several places.
Other helpful tips/info:
* I always ship USPS, using priority mail (2-3 days). I use flat rate boxes for anything not on the East Coast (Im in MD). Within a certain number of miles, depending on the weight, it might be less expensive to ship regular priority mail instead of flat rate.
* I make sure to let the cookies dry completely (at least 24 hours).
* If I am going to wrap them individually, I wrap them as I normally would in bags. If I am not individually wrapping the cookies, I layer them between sheets of waxed paper, being sure the waxed paper completely surrounds the cookies.
Here is a tutorial on CC. If i'm doing individually baged cookies i package the same way (with all the layers and peanuts) i just get to use a smaller box.
http://cakecentral.com/articles/127/how-to-package-ship-cookie-bouquets
oops! my pictures got deleted because they weren't pictures of food items. I'll attach them here....
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