Hi Jez, your idea is a good one and can be done easily and safely.
we've been doing trips like these for a while. recently sailed from elwood to port arlington approx 50km with some tacks between 2 - 6.30 pm on a 10 - 15 knot SE.
we are off to explore the fiji islands next week, have a look at our blog.
windsurftouring.blogspot.com
you just need the right board and sail and a mobile phone, water and a few snacks.
given the shape of the bay you'll go from downwind, reaching and upwind sailing regardless so just give it some thought and plan your day and if it doesn't work the first time sail in and call for a pick up. no dramas.
contact us via our blog if you want to meet up for some cruising.
matt
you don't need to tow a life raft when you're already standing on one. have a look at our gear on the blog and have a think about how you can stow a few items on the board if you need to. gavin le'seur sailed from melbourne to sydney on an old school longboard in the early 80's and had no problems. nick moloney also sailed from the prom to tassie unassisted, solo and non stop in less than a day and he even admits he wasn't a great windsurfer.
you'd be suprised the difference the slightest bit of drag makes to a board.
the boards we use are 295 & 373 litres but you would be best on a old school mistral longboard which can be picked up on ebay or seabreeze if you're lucky.
even when fully loaded up we can still sail quite comfortably on the plane for long periods so if you're towing something you'll have no chance, whatever you're towing will blow around behind you and stop you dead.
My neighbour has a big old Wayler (board only) that might suit you if you are interested.
Jez,im not trying to discourage you too much just keep you safe and not too dead.Towing stuff is hard work,try it with another board first and you,ll see why.Get some sailing practice in first,it may be a lot more work than you think.
Nick Moloney also said that the sail across tassie was the hardest sail he has ever done still and was lucky to survive after 22 hrs. Allison is still recovering from her attempt last year.
