Hey, good for you! I was planning the crossing last fall with my buddy but it fell through. Now he took his nice big stable Feathercraft K2 to B.C. and so I guess I will have to take the Caribou when I get around to it.
I did a search on kayaking and Tobermory and Manitoulin and came up with an outfitter "www.bypathorpaddle.com". I emailed them and they were very helpful, though as you would guess, they were tentative about the idea as they didn't know us or our ability.
I did ask them about their take on camping on an island on the way as they are private property, but they didn't think that would be an issue.
Obviously, it can be a nasty piece of water and I was going to come back from the island to Tobermory for the classic reason of prevailing winds.
I'm sure you'll do your research on weather and keep that marine band on, cause it can change in a hurry. I can't help but think that the seas and wind will really funnel though there, so I was going to check out normal powercraft resources and possibly the coast guard (find the closest base) or call Parry Sound and find out who you should contact.
Wish I was going with.
Let us know how it goes. There is not enough central Canada represented here, all these coasties!!