We think that from the top of the bay to the heads is doable in a day.. and that same distance would be the most that would need to be done in one day if island hoping.
Les and Mark did this on wally windsurfers more than 20 yrs ago.
I was once in serious training for a Bass Straight crossing on windsurfers and Steve and I had special Pan Am race boards made for us and sent out from France.
We found the biggest problem was having a support boat that could keep up.. and having to sail on one tack for so long.
It's a bummer that we never got to do it but then I don't think we would have made it unless conditions were perfect..and that's a big ask for Bass Straight.
DJ