Re: Degree of difficulty in circumnavigating Lake Superior ?
You can certainly circumnavigate Superior in that time Gregg. Superior tends to be fairly placid through that time, and in fact you'll probably be becalmed more than you'll be sitting out storms. August through the fall is usually when storms become more frequent. Given this, your fuel capacity may become an issue along the north and east shores (the Canadian shores). I'd strongly recommend you are well equipped for light-airs sailing. But be sure to have good ground tackle, and good squall capabilities as well.
It is cool up here most of the time, but good clothes and a basic heater is certainly adequate. You probably won't be swimming much ... unless we get another warm season like last year.
Anchorages: east shore heading north from SSM has fewer options until you get north of Agawa Bay/Sinclair Cove area. After that they become plentiful. I'd recommend you try for Michipocoten Island (Quebec Hrbr), although it's 25 nm of open water. Besides, you will likely want to pull into Buck's Marina in Wawa for resupply. Say hi to Brad (Buck) for me!
Tons of beautiful spots heading west & north from Wawa. Lots of big sandy beaches, and good holding just about everywhere. If you want, I could give you a list of our favourites.
The character of the lake changes once you hit the north shore. Turns rockier, with smaller anchorages, but still lots, and mostly good holding. Allouez Island off of Pic Island (near Marathon) is a neat place. And plan to spend a number of days in the Slate Islands.
I could go on... If you want more info just ask. Happy to help. We travel the Canadian shore almost every year. I've done the Apostles, and it's nice, but for me, the north, and particularly the east shores are the tops.
Why go fast, when you can go slow.