I have shipped to Italy. I was truly amazed by the leather goods restriction in the USPS site. Mind you, someone in the Japan Post system found the same restriction for Australia - go figure that one.
My items have always been sent by express post. The most expensive one was about $600 US. It got there. It took a couple of weeks, but I could see the tracking all the way on EMS. It went through Customs with no problem at all. I t was marked at as a used bag and was opened, inspected and released with charges. The buyer was fully up to speed on the customs duty. It was no drama at all.
I have sent several smaller Chanel and
Gucci items to Italy all with a minimum of drama. Their main issue is preventing counterfeiting. Italy is after all, one of the great countries of fashion and they try to protect their industry.
I only had one small tiny cheap item go missing. That one was only a $10 one and it was not insured. With agreement from the buyer, I sent a replacement after 1 month. The original turned up 2 months later. The buyer emailed me and told me it had arrived and offered to pay for for the second one.
Conversely, I have had a very unhappy woman who got extremely stroppy about customs duty. She didn't plan for it, didn't read the listing and was irritated. I gently reminded her to re read the listing. She sank without trace after that and no feedback.
So my experience has been a mixed bag.