If you're looking at the canal and/or Lakes Erie & Ontario as an obstacle to getting south rather than a destination, why not think out of the box a little..
Oh no maybe I misspoke in my OP. I am not looking at the canal as an obstacle at all. In fact that and the Hudson river would be the whole trip. I really want to explore the Erie canal. I also want to explore Lake Erie and Ontario. I just want to do it in a safe way.
I have a bit of offshore experience just not any in this boat. In fact we have no experience in this boat. Are there any good places within maybe say a two day sail of Oswego that would be good to launch from and that wouldn't be too treacherous?
Everyone always says the lakes can be tempestuous. Maybe I have just drank the cool aid too much.