Of course, there's one :) Sure, it's not the biggest in the world, maybe not the most vibrant either but there are definitely interesting companies and great people. A few people you could try to follow/contact to get a sense of what's happening in Italy (I'm not Italian myself, so they'll know better than I do). Stefano Bernardi, VC from Milan, Pietro Polsinelli, one of the guys behind licorize.com in Florence, of course Peldi Guilizzoni from Balsamic in Bologna (I think), Luca Filigheddu in Sardegna (twimbow among other things).
And that's only those I know or heard of but there are for sure many many more...
I guess the grass is always greener on the other side of the fence... Sure, people in Silicon Valley usually have a great attitude towards the web and entrepreneurs but it's also cut-throat competition out there. Don't believe that being based in the valley alone will make your life much easier. If you already have a complete team, a minimum viable product and some traction, then you'll be able to meet there people who know how to build up your audience and maybe get funding. There's definitely more experienced people there per square meter than anywhere else. But it's also a very expensive place in terms of housing/office space and talents.
Europe might not be as web-friendly but there has never been a better time for startups there. Think Seedcamp in the UK, startup bootcamp in Danemark, Hackfwd in Germany and many, many more.. There are loads of people in Europe taking startups very seriously.
At the end of the day, users don't care if you're based in Singapore, London or San Francisco. Also, you should be able to get an iPad not too long after anybody else in the US :)
In my opinion, if you're looking only at legal requirements, the Valley is an awful place to start a company as an European entrepreneur. I explored a few years ago the opportunity to start a business there and it didn't take me long to realize that legal fees would eat up all my capital before I had even a chance to start writing a line of code. Moving your business there once it gains a bit of traction (and funding) is probably a better idea if that's what you want to achieve.
Now, legal issues are tricky everywhere. But one thing you need to think about is how labor intensive will your business be ? Some countries like France or Spain make it almost impossible to fire people whereas countries like Ireland or Switzerland offer much more flexibility.
But chances are high that you won't start by hiring a lot, right? Then, what you need to focus on is: how easy is it to grow a business and what would happen if you fail. You want to be able to add shareholder easily, while keeping administrative duties under control and you don't want to get into too much trouble if you need to file for bankruptcy. I heard Germany and the UK might be good choice if that's what you're looking for (not very sure though, please check ;)
Finally, if your startup will not be labor intensive, nor capital intensive at first, my advice is: don't overthink legal aspects. Go where you have the best networking opportunities while being able to hire great people at best cost. And that might just be exactly where you're living now...
Oh, one last thing. Europe has everything you'll ever need in terms of talents and capital. So I don't agree when you say that you're "less lucky to have been born in Europe". But that's another story ;)