I know this may seem elementary, but this information may be helpful to anyone wondering how to ship cigars. Remember, your reputation on this or any cigar board depends on your actions. This includes the care you take in shipping cigars for contests, trades, sales, splits, passes...etc.
Step 1) Inspect the cigars you are going to send. Check for cracked feet, damaged wrappers, anything that looks hinkey. If it's a dud, replace it or refund it and communicate with the recipient about any problems.
Step 2) Select a box and test it for size. This is pretty common sense, and I'm using a USPS small flat rate box for illustration purposes, but you can basically use any sturdy cardboard box. Anyway, take a look and make sure there will be some room around the cigars for padding, or shock insulation. You don't want them so tight you crush them, but you also don't want them banging around in there.
Step 3) Ziplock those babies. Don't cram the shit out of 15 cigars in a quart bag. Ziplocks are cheap, split the smokes into 2 bags. Sometimes, if I'm worried it's going to take a while for delivery, I double bag for some added buffer.
Step 4) Package, pad or shock insulate the ziplock bag. If I could, I would use bubble wrap every time. It just seems to make the process easy, however it's not always available. Other options are peanuts, which can be a PITA for the sender and recipient, newspaper, or one I figured out recently, used plastic grocery bags. They fluff up nice, and really conform to the box, and the cigars.
Step 5) Seal it up, label, send. I use a tape gun for this, but if you don't have one, they sell disposable rolls of it at places like staples, and probably your local grocery store or 7-11. I like to put at least one piece across the self adhesive flap (especially if I'm re-using a previous box.)
Step 5A) I forgot. This is VERY important. ALWAYS get delivery confirmation. ALWAYS, even if you're sending it to your best friend, or your Grandmother. It's cheap, and it's proof.
That's it. Happy shipping. That is as long as the failman doesn't smash your package to smithereens regardless of this tutorial. In that case you're SOL and will have to re-send the package.
Link to Craig's post about shipping to Canada etc.