Welcome to the HUBB!
You probably won't like my advice: I wouldn't take a bike or any other gear that I can't afford to lose. However, how is an insurance c. going to know how long you have been on the road?
Buy a decent chain lock and use it, every time. Attach the frame to something solid, like a lamppost. Avoid parking in big cities, especially don't park repeatedly in the same place. Avoid the Med coast like the plague. It's no fun riding there anyway and theft is rampant.
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