Perhaps a silly question, but if you are IR rated and equipped, why not file a flight plan routing direct overhead MAN? A South-North transit through the overhead should cause ATC no trouble at all
Because he's on his holidays away from flight plans + positive control etc, and probably wants to merrily cruise along at 1000 agl taking in the sights, farting and lighting one fag after another till his hearts content with nothing but the friendly banter of SI to aid him on his way.
Well that's how I would envision a stress free flying holiday anyway.
Have a good time and enjoy the highlands.