It's been said before elsewhere, but always worth repeating....
I prefer to ship cigars individually bagged and double boxed with free delivery confirmation via usps priority.
The best ( ...and most cost effective!) system I have found for shipping up to ten cigars:
Order these small priority boxes, free from the usps:
Small Boxes
...and these large priority boxes, free from the usps:
Larger Boxes
...as well as a roll of this priority tape, free from the usps:
Tape
...and these baggies ( not free, but inexpensive @ $7.78 per 1000 plus shipping!) from Veripack:
Baggies
*Individually bag cigars to protect from damage.
*Place bagged cigars in SMALL usps priority box, along with with foam peanuts or bubble wrap!
*Insert filled SMALL box into LARGE usps priority box.
*Seal with usps priority tape.
Print out priority label with FREE delivery confirmation number here:
Shipping Label
Hope it helps!