Eastern Seaboard to Lake Onatario

The ICW will take you to Norfolk, Va. then into the Chesapeake Bay where you can go to the ocean or up into the C & D canal to the Deleware River down to Cape. May, NJ. That's as far as you're going on the inside with that boat (too many shallows through NJ) untill you enter NY harbor. Once in NY I think this link should help: http://www.nyscanals.gov/

I always take the ICW eastern branch past Coinjock to Norfolk. (Dismal Swamp route tends to be slow and often shallow). From there if the seas are light I head outside to Ocena Beach, Md., then up to NY although you would probably stop around Atlantic City. If the seas are rough I go from Norfolk, up the Chesapeake to the C&D canal, over to the Delaware River and back down to Cape May, NJ. The inside from there is nearly impassable for a 5' draft, especially south of Atlantic City. Just not worth messing with, but the inlet areas are fine if you need to come in at A.C., Barnaget, Manasquan or wherever.
Once to NY you'll head up the Hudson. From there I'm a little concerned for your height which is why I refer you to that link. You can get all the info you need about the NYS canals system from that.

You cannot get into Lake Ontario from the Hudson River/NYC with an air draft of 23'. There is a bridge on the North side of Troy, NY on the Erie Canal that has an air draft of 20'2. Now keep in mind this is minimum clearance and when I went through it was a bit higher then the published 20'2.

If you can get it to 20'2 then you go up the Hudson, across the Erie Canal to Three Rivers and then north to Oswego, NY and into Lake Ontario and then you just hop across Quebec. If NOT, then you need to take the ocean to the St. Laurence canal which is many many more miles

Thanks for that Capt. J. I recalled hearing that and couldn't find a way but didn't want to put the kabash on it having never gone that far up myself. The outside run from the Cape Cod Canal up to the Straits of Canso is a lot of open ocean running (about 38 hrs.). When I made that run we left Ft. Lauderdale in Late March and had to leave the boat in the Strairs for 3 weeks due to ice. So it's strictly a late spring to early fall trip. Is it possible to drop your mast and lose the 3'?

What kind of yacht are you planning on running there? I would really measure what you have. Call the dockmaster at Troy, NY and ask him what kind of clearance is at the bridge. When I went through it was around 22' because the water level was lower. You could also flood the bilges to get the boat down a bit further, it is freshwater and you could just open a seacock and add 10-12" water to the bilge and get the boat down probably 8-10" that way. A friend of mine had to flood the cockpit on a 66' Ocean to get it through.

I was able to get a 75' Hatteras MY down to 18'6 just by lowering the radar arch and masthead. Also a 63' Ocean SF is only 19'6 to the top of the radar on the factory hardtop.

What do you have mounted on your hardtop? You should be able to get to under 20' while still leaving the radar on if it is mounted flat on the hardtop. I don't know the configeration, but it sounds pretty easy to get to where you need to be height wise. The Erie canal route is a lot shorter and faster to the great lakes. You would want to stop in Troy, NY at the city docks and take your stuff down there. Then at Oswego, you can put it back up.

From NYC, you should be able to get to Lake Ontario in 5 days. Another day to the Welland canal, a day to clear customs, go through the canal and you're in the Erie canal. BUT yes, you have plenty of time to get into the great lakes before winter. I'd say you have 4 weeks of time maybe 5 weeks to get there. The Erie Canal is very scenic and was my favorite part of the entire great loop. Check the NY canal system website and see when they go to reduced lock hours. Also, I anchored everynight on the Hudson and Erie canal except Oswego and one night right before that. There were plenty of places to anchor and you could run until almost dark that way.

I'm not familiar with that Great Banks, but I would guess you could get the height down pretty easily to where you need to be. A normal Satellite dome doesn't typically stick up that much.