Ahoy!
The problem here is that you are going from one country to another, and maybe through other countries.
I cannot see a car hire company allowing this and I cannot see an insurance company covering you in other countries than their own.
You might try public transport and hire a car as needed, or as possible for days out. There are steep one way penalties for picking a car up in one place and dropping it off in an other as they have to pay someone to drive it back.
Flying is a lot easier and quicker and not too expensive if you book early.
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