I grew up on Halvorsen style cruisers in Cowan and really love them but would not use them in the way you are suggesting.
Firstly, they will roll like pigs outside, and the 15 miles from North Head
will take you around three hours in good conditions.
Secondly, old wooden boats need work. I have vivid memories of trying to sleep under plastic sheets
during the first downpour after a hot summer week, and of helping Dad cut out chunks of rot
, not to mention worm below the waterline.
It may be worth looking at a diesel
powered semi displacement
cruiser of fibreglass construction. May not be quite so romantic, but in the end you will probably find it more useful.