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@SoYaap
I did a longish tour from the UK > Greece > UK (6500km riding) a few years ago and stopped for a family wedding in Tuscany along the way the riding near Arezzo and Perugia was fantastic. I also really enjoyed the section from the Czech highlands to Dresden. I'm based in Zurich most of the time so let me know if you need a place to stay if you're coming through because otherwise accomodation is damn expensive.
On the planning side of things, I set off on this trip with the route for the first several days planned and a list of a few major destinations but otherwise I just winged it and did a bit of planning during breaks in the day. I found it super helpful to have a GPS that allowed for easy map browsing like the Garmin Etrex 20/30.
Also on the bivvy vs. tent question I would rather have a tent for a trip like this. I toured in Japan for a month with just a bivvy and it was fine but I'd miss the small things like being able to get dressed inside the tent and having a bit more space to shelter when it's raining.