Yep. In the UK at that time, Italy was associated with Italians in Britain, pre-war, running ice cream shops. A run to Milan or Turin, was considered a 'milk run', to an extent, so, rather than show a bomb on the mission tally, an ice cream cone was often used.
I haven't heard of a 'R' being used to denote a Ruhr target - and the majority of targets were in the Ruhr anyway. Without seeing the symbol - and the nationality of aircraft and Air Force - I would guess that a star and 'R' combination would mean a 'shuttle' mission, either by USAAF or RAF Bomber Command, where a landing was made in Russia, for example at Yagodnik, before returning, via another target, to the UK (or Italy if 15th USAAF or MEAF).
Of course, again depending on the aircraft in question etc, it could be related to something specific to the unit/aircraft involved.