Ok. I’m taking no liability for what follows, ok? In Italy free camping is permitted, maybe.
Italian law define camping as the building of a fixed tent structure for no more than 48 hours, and bivouac as the staying in a tent structure overnight.
At a national level italian law allows for camping and bivouacking.
Then another law (D. Lgs. 31/3/1998 n. 112) transfers every aspect of tourism’s related laws to local authorities, so that “camping and bivouacking is allowed unless explicitely forbidden from the local laws and signaled with the proper signposting”
From here on…is a total mess. Every county has its own rules, every province of every county has its own rules, every city in every province etc. etc.
Generally speaking, and with reference to your itinerary:
meaning: take no offence but I’m not going to read through every law book of every city to search for every detail
Conclusion: welcome to Italian bureaucracy.
My opinion: avoid it. The risk is too high, and there are so many wonderful place in the world without the need to risk your time in this often overcomplicated nation. Go cycling in Provence, for example.
My suggestion if you really feel the need for it: Lugano-Genova can easily be done going through Piemonte, where camping is allowed. Venice can be reached from Lugano through Trentino Alto Adige, where you can risk camping.
Edit after comment from OP
Sorry,, but I have not been able to find a clear indication of how laying down with a sack or a mattress is considered. I’m not a lawyer, in all honestly, and this things are a bit of bordeline.
Technically, bivouacking and vagrancy/roaming are more or less the same, it just depends on the context. In your case, if you were an perfectly capable of speaking Italian it would be easy to explain what you were doing, otherwise you risk a little bit everytime. Honestly, if you want to do your bike ride, bring a tent and sleep in it. Still questionable (by the policeman) but at least a lot lot easier to understand. And you can put your bike inside, that at least will grant you that your bike ride will last more than a day ;-D
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