OK noob, here's what I do...
Take cigars that are in cello and put them in a ziplock bag. Keep them away from the naked cigars if possible, or put the naked one in a ziplock for one...
Get as much air out as you can, seal bag.
Wrap that bag in small bubblewrap, and tape to make bundle.
put that bundle into box and determine how much packing material you need.
Whether its pillows, popcorn, scrunched up paper, et al doesn't really matter at that point since the bubblewrap will protect your cigars. As long as the bundle don't rattle around in the box, its good to go.
Cigars will last 2-3 days without humidification. If you're sending them to the sandbox, or Japan, you would need to put some kind of humi in the ziplock bag before you seal it.
Tape box closed, visit the PO, ship priority with delivery confirmation, and away you go.... 🙂
See, its easy.
Now send SteveS a cigar already...