Firstly, Diana sailing a Top Hat single handed is easy even if you don't have big muscles. Just make sure you raise the main before you drop the mooring, have a furling headsail and the auto tiller ready to go. I usually stand mid cockpit with the tiller between my knees and work the sheets from there. Trying to sheet on as much as possible in the luff means you don't need much winch handle action. Of course, it all takes some practice, but if Jessica can do it, anyone can Even getting the anchor up isn't that bad once you work out how. If you have crew and the weather is reasonable, the trip to Pittwater isn't all that hard either. I've done it in a North Easter, and while it took longer than I'd have liked, it wasn't hard or uncomfortable.
Pittwater is a big place too, if we're anchoring then we could do Patonga, there's plenty of beach and while it's a bit further by car, there is also a Palm Beach ferry there. I'd be happy to take a couple from Careel Bay if anyone is game to go aboard my old tub.....
PM Me if anyone is in need of transport from Careel Bay.
Michael