First and foremost, do you want to just send a "novelty" amount or you thinking "hey I could be the dope man back home with this shit"?
When you have to sign for some shit is when you get your ass ripped apart by the alphabet boys.
Here's some things to remember if you do decide to do it:
-Make sure the recipient knows that there will be a package with something nice in it and you will share, but to be clueless if it came down to it.
-Consider the cost of all this before you even get there. International shipping ain't cheap and you want their as fast as possible.
-Don't try to do all this preparing the the night before you leave, make sure its one of the first things you do when you touch ground and find the shit. Take out what you may need for the remainder of the trip and wrap the rest. You want to make sure your arrival home as well as the package is roughly the same day.
-MAKE SURE ITS JUST WEED. I know there's other shit in Jamaica your friends with you might want to have back home but KEEP IT GREEN.
-UPS has 8 Locations in Jamaica. j/k
-Since its not a domestic package, you would want to KEEP QUANTITY TO A MINUMUM. This is a Federal Offense and people usually get charged for each state/province the package was sent to before it reached its destination. Don't send an amount you don't mind losing out on. You have to look at this like its not gonna work anyway just so when it does, there's an added bonus. Mailing out big ass boxes from Jamaica to the USA is already suspicious.
-WRAP THE FCUK OUT OFF IT! Air-tite the stash in a bag and place that bag in a bag with a few of the smelliest fabric sheets. Use plastic wrap, clear duct tape, small tupperware/rinse & re-use containers. Wrap it til you cant smell the fabric sheets. The more layers the better, but keep your package small. Its Christmas time, so things wont look too bad. Just put boxes inside of boxes. Best to hit Walmart up for most of this shit before you leave
-DON'T SEND THE SHIT TO YOUR ADDRESS and use false TO and FROM names! Just use the from address of a souvenir shop as the FROM.
-Send it to an address that someone of the opposite sex than the name on the box resides at. So if Kevin Lewis is on the box, send it to Kate Stevens. BUT DONT HAVE HER SIGN FOR IT!!!!! Have the carrier leave it at the door. They might knock if there's a car in the drive way. But if they do, tell the person not to answer and they'll just leave the package on the welcome mat.
-AVOID SENDING IT TO AN APARTMENT! Especially if the apartment has a doorman, a locked door to get in the building, and a dumb ass apartment number like 4 digits long. Since the name on the package isn't of anyone who lives at the address you have to depend on a simple address for the carrier to drop it off at. Usually the alphabet boys jump out on you when you confirm with the carrier (who is really an undercover FED) verbally that yes, I am (your name here).
-If you are not a native or used to be a native of Jamaica and still speak their native tongue (Patwa/Broken English), DON'T DROP IT OFF WITH THE CARRIER YOURSELF, especially if you're white, pay a native to send it for you. The only thing they have to do is pay and get a tracking number. You should have either wrote the address with a sharpie on the box or sent the Native in with a piece of paper with 2 address' and cash for the transaction.
Once you have successfully dropped off the package. TRACK IT via the internet every second you think about it. It hits several different locations before it gets to its destination, as long as the package is scheduled on time, there should be no problem. When there starts to be hold-ups and redirection because of "problems with the engine" is when you really need to go check and see if you sharted (fart with a little bit of shit in it)!
Good Luck dude!