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julesmoto said..
I have given it some thought. We holiday in the Whitsundays every Winter and I find myself staring at the water wishing I was on my boat.
Not exactly a trailer sailer but I was thinking that something like a Ross 780 might be good even though putting up the mast is a pain and it's not exactly easy to tow. On the plus side it can be a caravan to sleep in on the way to far away places.Not exactly a dinghy I know. A centreboard however has great advantages in beautiful sandy areas otherwise inaccessible to my keel yacht.
That's exactly the direction I have gone now after many years of cruising smaller trailer sailers and sailing kayaks. I have done 8 trips to the Whitsundays now 4 when based in WA and 4 from southern NSW and lots of others in other places. :)
2x in Jarcat 6's trailable catamaran. Couple
1 x in a Farrier 680tt trailable trimaran. Couple
1x in a Hobie Adventure Island sailing kayak ( car roof top carry) Alone
1x in my previous Imexus 28 3.2 ton trailable yacht. 3 on board.
1x in a charter 36 foot catamaran. 7 on board.
2x in 32/33 foot mono charter cruising yachts. With 2 and 3 respectively. Next year (now retired) I will take my more recent Imexus 28 which I have set up specifically for long range cruising for a few months at a time. Couple with short term guest onboard.
After lots of small yacht cruising experience I feel this is about the perfect size and maximum flexibility option for a couple with occasional guest.
All the above yachts and kayak had plus and minus features and benefits.
Too small and it's just camping on a boat and bigger, non trailable and or deep keel mean hard work to get up there from southern Australia ( or expensive chartering) and many limits to mooring/exploring location choices.
Re the above comments about the negatives of putting the mast up and trailering it's all about appropriate systems in my view. :)
Whilst my mast is pretty big at around 30 foot and the yacht over 28 foot with internal standing headroom, my mast, rigging, launching and retrieving have all been designed as relatively quick one person exercises.

Having done many years in small sailing platforms I appreciate all their benefits but like the ex tent campers and ex backpackers (also been there done that) many now have moved to caravans, campers or motorhomes as there comes a time when a little more comfort is appreciated!
Best wishes with your proposed dingy camping, my only suggestion is something like a Hartley 16 opens up staying onboard that become more difficult in an open dingy.