I haven't tried "cooling" a box of plants or fish, but when I ship I usually put everything into a styro cooler, then pack that into a cardboard box with newspaper or peanuts to cushion the individual bags (fish are usually double bagged, aquatic plants usually single bagged with no water, terrestrial plants single bagged around the roots with a damp towel or two).
If you're worried about saplings shifting and breaking in the box, find a bamboo stake about the length of the tallest (from root tip to top) and tie all of the saplings to it in a couple of places. That way if anything shifts the stake will stop the live plants from hitting the ends and breaking....
Hope this helps!
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