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Regardless of what has happened on the Federal or Provincial level, it is illegal for private individuals to ship wine. However how many of us have, and how many of us have been caught. Probably nobody.
No carrier (ups fedex dhl) will ship wine across the border unless you are a licensed winery, wholesaler or distributor and have a fda registration number or tax id number. Wine is treated as a food item and in order to cross the border a prior notice must be submitted to the FDA. After 9-11 it's become a nightmare

You may wish to take your chance, cross over the border and drop it off at fedex/ups not disclosing the contents.
a short story about what happened to me ..

a wine & spirits rep sent me a couple of bottles of wine back in october as a thank you gift. i don't know how he shipped it - likely canada post but it never made it to my front door. within the same province too!

the rep re-sent the wine via fedex but the original package? who knows .. pisses me off that someone is enjoying my wine though.

would canada post confiscate it and not tell the sender or receiver?

if you're shipping that rare belgian beer .. make sure you get a tracking number - regardless of the method of shipment you choose.
Shipping from Canada to USA might be illegal, depending on the states. In any case it doesn't look optimistic. If you are within driving distance to the border I strongly recommend shipping from the States, plus it's cheaper. Just drive across and mail it. If quantity is beyond 2-3 bottles you probably have to pay a minimal duty. (But its literately pennies compare to bringing it in the opposite direction)

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