I was thinking of sailing over to the main bay in a SE seabreeze, leaving from Middleton, but actually going over on the ferry would be good. Could be interesting in a howling westerly to see how rough it is in the shallower areas.
I drove down that way this afternoon and you can see the island in the middle of the bay in this photo. Could be a nice bit of flat-water in behind that island? Also a shot looking up toward the isthmus between north and south Bruny.