On the way back to Melbourne everyone rated the trip and what they thought the best and worst bits were:
My son would rate it 9.5/10! He said the best bit was the sailing we did, in particular sailing under the Sydney harbour bridge! He didn't have a worst bit.
My daughter rated it 9/10. She said the best part was all the swimming. She said the worst part was tearing the mainsail.
My wife would rate it 8/10. She said the best part was watching the NYE fireworks from the boat. The worst part was tearing the mainsail.
For myself I said it was 8.5/10. The best bit was the NYE fireworks. The worst was motoring into the 25 Knott wind and waves off middle head. Ironically my family were all down below snoozing when it happened so they missed out on all the fun.
We discussed what gear we brought was useful and what we should have left behind. The prize for best gear was a tie between the Bimini and tender. The weather in Sydney was HOT, so having some shade to shelter under was essential, both while sailing and at anchor. Often we would all be cramed together under the spot of shade rather than sit in the sun. In my backyard at Port Phillip bay we don't have much use for a tender. It seems anywhere worth going has a jetty or marina of some sort. In Sydney having a tender increased our flexibility dramatically! There were several places we could only access by tender. In many cases it was also easier to anchor out and get to a shore via the tender than risk moving the boat into an overcrowded and unknown situation.
As for useless gear: When I went to the Whitsundays I regretted not bringing a selfie stick! This time I brought it and never used it. The sailing trips were too short and and the water to busy get it out and setup. The other prize for useless goes to a large wooden plank I use for tying up at the fergerson street pier in Williamstown. It's used for sitting between the pier and the fenders when we are tied up at locations that only have vertical wooden piles. It turns out there is nothing like this in Sydney - everywhere we went to had the floating pontoon style jetties. Consistently this large piece of wood spent the whole trip strapped to the rails!
Would I do the trip again? I think it's worthwhile doing once - the fireworks on the water were incredible. But having done it, I think I would prefer to spend future NYEs in a quieter area. I'm somebody who is quite active and has a hard time staying in one spot. I tend to spend my holidays running from attraction to attraction trying to fit everything in. I like the buzz and bustle of citys! But Sydney passed even my limit. I think in future anchoring for a week off some quiet and empty beach where the kids can swim and we chill in our camp chairs sounds like just what the DR ordered. I'm thinking for a future NYE trip giving the Gippsland lakes another shot or trying some of the various lakes in southern NSW.
All up: I'm very happy I did Sydney Harbour on new years. But I'm not sure I would be happy to do it twice