The biggest problem will be clearing customs in IT. Your country is
: notorious for customs clearance issues- I say with no offense
: intended.

As far as I know Italy simply applies the European Union rules about customs clearances from extra European countries. It's not a national rule.
In addition there is a national VAT tax, but it's lower than many other european countries, and it's only due in case you are buying something not already charged. So, if the F1 bought in Oregon is USA's vat included, it won't be charged again in Italy. And no VAT is needed in case you are shipping your own stuff to your own home, because VAT is sort of transaction's tax and there is no transaction between you and yourself.
:D
In case of troubles, you can simply show how you built that kayak in Oregon and just want to bring it back home in Naples.