One problem is that when planning VFR one needs to plan a route OCAS. This is what takes a lot of time in VFR planning.
A lot of people don't do that and I suppose they get lucky on transits, but you need to be assured of radio contact. Lost comms used to be common in France (nobody on the FIS frequency) but I guess it is a lot better now.
My way of doing VFR flights over terrain (assuming the plane actually has the capability to fly over it) is to pick a starting point which is fun to stay in anyway (in case you have to stay there a few days), wait for a day when there is little cloud cover over the terrain, and go straight over the top.
You get views like nothing else, and enough amazing pictures for a year's worth of screensavers.
In most mountain regions there are loads of valleys in case of engine failure.
Otherwise, any VFR route can be planned with the charts spread all over the floor and enough time. It often ends up quite ridiculous but one can usually get enough CAS transits on the day.
If one is stopping in uninteresting places, one needs to be flying a fully de-iced plane with a 25k ft ceiling, as a minimum, and this is true for both VFR and IFR.