Looks like you would come down into the harbour from the north west of Flinders Island (Tom Thumb Islands). Leaving to then go south would take the same route out by the looks?
When you doing this
Certainly looks safer option. Deeper& less obstructions but is that a shipping lane? Never sailed there yet but will be soon. Im not sure but i think wollongong harbour might be nicer to the north for an overnighter.