you can sail everywhere on the western side of a line drawn between long nose point balmain and greenwich go further than this and your in trouble. Tried sailing from Dobroyd pt to manly when i was younger but only managed to get just past the harbour bridge as we were pulled up by the water police and a waterways patrol boat. got taken back past cockatoo island and threatened with gear confiscation as a minimal penalty??? or a fine of a few hundred dollars as maximum penalty??

if we ever tried again

Dont they have anything better to do!!
When theres a NE'er you can sail from hunters hill seems like the wind excellerates here between the eastern shore and the western shore so it can get real windy and theres ferries goin through this small passsage every 15mins so if you want to jump their wake you can go for it here. Theres also heaps of really large pleasure craft traveling through here that leave an even bigger wake sometimes.
if you really wanna hop wake you should probly just go to long reef or wanda the pacific ocean leaves the best wake around and much cleaner winds