Not sure what you are trying to accomplish here. If your objective is to just get there it can be done. However, you are missing the whole point in my mind. You are looking at about a 1000 miles just getting to the ICW, and then you will have to push down it to stay ahead of the weather. Why not just ship the boat?
September and October are the best kept secret in the north, but you need to be prepared for it. Diesel is very hard to find on the water after 10-15 in the north. After November 1, forget it till late April unless you are carrying jerry jugs from a truck stop somewhere.
If your boat is in Bayfield you must have an idea of that time of year in Superior. Would you take a two week cruise at the end of October? I don't think so!