Beware of trying too hard (and I don't mean flying...) but:
The harbour scenic is pretty red-letter stuff; however you might find it a bit 'busy' if you're relatively inexperienced, and you'll spend a lot of time paying attention to the pilot stuff, not her. Ditto victor one down the coast.. Procedures fairly simple - see Ersa / sydney basin vfr guide (on the casa website if I recall correctly..)
My favourite flying 'date' involved finding somewhere interesting / with a decent restaurant/winery, and 'just dropping in' (apparently spontaneously) for lunch. Unfortunately all my location suggestions are in victoria, not nsw.
All that said, I've also done very well on the aeros trip too
