Sounds great TDW,
We have just started venturing further afield in baby steps, Port Stephens is going to be next, Jervis Bay shortly there after.....
When we reboat the plan is Queensland/GBR to shakedown, and then depending on time/money/how we are finding it all, we would do a similar loop to what your thinking turn right at Cairns and go Louisiades, Solomons, Vanuatu, New Cal and then home.
There is a thought of going from here to Lord Howe as a shakedown. However Lord howe to me is far scarier than 3 months of sailing up to Cairns. It is essentially 400ish nms of Tasman Sea. For beginners like us that isn't a small feat.
Baby steps are good.
Jervis is our next one. We didn't get up to Port stephens, weather and time mucked up the plan . Got to Newcastle then ran out of time. Jervis should be a nice wee cruise. Chance to do an overnighter, bit more of a test of the old navigational skills. I'd like to do my Yachtmaster so will need to do the passage requirements. I've done more than enough over the years but not recently so want to do it again with it all signed off etc. YM Coastal is 300nms with two passages of at least 50 and one of at least 100 , from memory. Jervis is 75 (return ergo 150) and Port Stephens 65 (130) so I'd like to do Lord Howe as the long one. Would give me much more than I need. That would also give me passage time of at least 10 days, need 15. Run up the coast to , say, Coffs would take care of the rest. Then again we are also thinking of doing the Heaven Can Wait this year.
Ref Lord Howe, yes it is a doozey. Sydney is not the best place to start from given the prevailing is probably going to be from the NE. Out of Sydney that means a hard beat to windward. Better to get up the coast a bit and head out from round Coffs or Port Macquarie. If you get the weather right then coming home is a reach. If time permits, and for those of us still working that can be a snag, then a port hop up the coast would make for a very pleasant enough shakedown cruise before heading offshore proper. Now, given that the run up the coast will be a beat it would be nice to be able to pop into port most nights to freshen up. The harsh reality is that heading north from Sydney is almost always going to be a slog unless you are lucky enough to grab hold off the tail end of a southerly. Then you are left with a reach to Lord Howe which is what you want for a first offshore.
I've crewed on longer than passage to Lord Howe but not skippered. Going offshore in one's own boat is indeed a big step and yes, it makes me somewhat nervous to think about it, but to my mind overconfidence would be worse than a slight case of the jitters.