Being curious what whinny the poo wrote I did the only thing any interested person would do, I used google translate and surprise surprise it came up with exactly the same (almost perfect English) text that Bernard quoted.
If it had been proper Italian language the English translation should have been disjointed.
A couple of examples from German to English:
O Christmas Tree O Christmas Tree,
How loyal are your leaves!
You not only green in summer time,
No even in winter when it snows.
Silent Night Holy Night
Everything is sleeping; lonely wakes
Only the faithful sacrosanct couple.
Gentle boy in curly hair,
Having sent Whinney the poo's message to an Italien, her comment: This is not text of an Italian speaking person, it is typical of translating the words from a dictionary.
The thing about google translate is, all it does is translate word for word, just like using a dictionary. It doesn't translate into a different language.
So no at the moment we don't know winston 1's Italian abilities, all we do know is he can translate English words into Italian words using a dictionary such as Google translate