Just read this thread, as I was thinking about Italy myself this year, so was interested, but my reply is to do with getting suitable transport.
A lot of overseas visitors to Europe think it will be a fairly simple solution to buy a bike here and then sell it afterwards, well I regret to say it isn't any more. The European regulations are now very strict on visitors buying vehicles, as this seems to be a favourite ploy for the 'seedier and more terroristic' elements of society.
If you buy a vehicle registered anywhere in the European Union now, you must register it in your name within 4 weeks. To do this you need a 'permanent' address in the country where the vehicle is registered. Insurance companies will only issue temporary insurance cover until the vehicle is shown as registered in your name at a permanent address. In the U.k. and in France the insurance companies, registration authorities and the policing services are all interlinked by computer, so it's easy to check. You won't get Insurance to travel outside the country of registration until it is registered in your name.
Don't even think about travelling without insurance! and in Europe it is a legal requirement to carry all the correct documents with you. Anything that doesn't match up or lacking may result in the vehicle being seized and possibly destroyed.
Hiring a bike or borrowing one with permission are solutions, though you may find getting insurance for travel outside the country of registration a bit of a problem if you are not the owner and have an overseas driving licence, otherwise shipping your own is the only other solution.
Whichever way, good luck and enjoy Italy when you have found your solution.
-Not all who wander are lost ( Tolkein)
-'' Live life then give life '' (www.lltgl.org.uk)