To me, the absolute best GL cruising is the north & east shores of Lake Superior. This is the Canadians shores, but itís not a nationalist thing. Itís just that the south and western shores, outside of the Bayfield/Apostles and Isle Royale, arenít all that interesting to me.
For rugged beauty, for wild and remote anchorages, for mostly untouched wilderness, for solitude and wildlife, and for big water sailing, itís hard to find a match for the north (and east) shores anywhere outside of areas like Newfoundland or the PNW.
The problem you face is, it is a big area, and relatively far away from your ultimate destination of Oswego. A 32í sailboat is not a speedster, so unless youíre really willing to put in lots of long, hard days, or a few overnight sails, the north shore might be out of reach. Anything is doable, but itís probably not desirable.
Given my approach to cruising (read my signature line
), Iíd probably head over to the Green Bay area first, and spend some time exploring there. Then Iíd head up into the North Channel, and take the slow cruise east. If you arrive here before the end of school it will be relatively quiet. It gets a lot busier in July/mid-August.
Meander through the North Channel, then head down Georgian Bay. Take your time. Lots to see and explore here, but also more people/boats. Take the Trent. Iíve never done it (but know it quite well). It would be a fascinating float through history.
Youíll flush out in the Bay of Quinte. Personally, Iíd get the mast back on there and go explore the Bay and head up into the 1000 Islands. Youíre no longer in wilderness, but thereís lots of beautiful places to see, and itís still possible to find quiet anchorages in Quinte. The 1000 Islands will be busy, but are still worth it.
From there you can head back into eastern L. Ontario, passing through the Henderson Bay area before finally making your way to Oswego.