Gulf to Great Lakes
Be sure to go to jazz fest while in New Orleans. There are a lot of marinas and sailboats on the gulf and lake Ponchartrain. I''m sure you can find someone for sailing lessons.
Cool about the bikes. My wife and I did the Bike ride Across Tennessee(BRAT) twice.
Unless you have a compelling reason it would probably be a lot better not to go from New Orleans to the great lakes. Unless you are considering the great circle route up the east coast and then back down the rivers. We had a lesson today while motoring up the Mobile river. When you can only motor 5 kts going into a 3 kt current is slow!!!! But when we turned around it was nice going 8 kts.