Last year I left from Meaford sailed to Winfield basin at the tip of the penisula to providence bay then stayed at Great duck island up through missisauga strait and up into meldrum bay. From there up into Superior.
On my way back I ran from the SOO back to winfield basin acrros the south of manitoulin.
If you have any questions about this ask, but I will tell you this.
If you are asking weather you should go the answer is this.
Can you sail single hand in winds of 30 knots and seas of 3-4meters AVG?
and can your boat take it?
Answer yes and that would be my minimum critera to say go for it.
As for the weather I went in July and It was a bit cool but I realy enjoyed the sail, generaly you will be beating all the way because the prevail winds and the closer you get to the shoreline of manitoulin the more they seem to funnel right in your face.
If I was planing that trip, (and I am planing somthing similar this year) I would return via the south of manitoulin to take the prevailing winds to your advantage.
The way home was a blast down wind and was realy warm and sunny even with winds of 20k It took me 36 hrs from the Soo to wingfield.
You will be well off to get the canadian sailing directions even for the north side
Canadian Hydrographic Service
You will be suprised at your options for ancorages, most people just use the ports guide. you seem like the type to go in more off the track place like me.