Yeah wine glass bay looks awesome to SUP into. But there is no road access anywhere around there. The only way there by land is over the trail which is a challenging hour or two walk IIRC. And thats without carrying a 12 foot board!
In perfect conditions and with the right board (say a 16 foot) i think you could paddle from Coles bay to Wineglass, leave the board on the beach overnight and walk the hour back to Coles bay to sleep. Then do the reverse the next day.
Ideally you'd want an option to pull out if you needed to along the way. But I';m not familiar with the terrain that far down the peninsula. Would Schuten island be a good port in a storm I wonder?
This is what I might have a crack at if the conditions are amenable. Can always shorten it just to Promise Bay