I would love that drive I have driven up on a Honda 400/ 4 in 77 from Palermo to the UK as we did a France Spain . Morocco , Algeria, Tunisia & back trip as a student.
Have been down to Sorrento in a Mog & to the lakes . I would 't rally it but I would cruise it. That is practically my dream trip except perhaps via the Sud Tyrol & Bavaria.
SWMBO though needs 5 star hotels.