The insurance shouldn´t be a problem, in the first link i posted, the comprehensive cover costs 20€ a day, ( %5 of damage on own risk, or 1500-2000€ by total loss, worst case scenario) , a scooter is 80€ a day with 200km limit, every km more driven costs 0,2€, a honda cbf 600 120€ per day and 200km more km 0,30/km.
the insurance for my own bike ( only casualty insurance) costs me 25€ a month....
btw how did you plan to travell from germany to southern italy or greece? per train? or plane? your destinations are a little bit wide spread across europe.
one month is a nice amount of time, we drove our landrover from austria to northcape and back in one month, nice trip, but fuelcosts were eating up a lot of our budget.
mfg
A.W.