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I loved Newfoundland - Nova Scotia was nice, but Newfoundland was great. The problems are:
1. Heavy fog
2. Very changeable weather
3. Strong winds 35 knots is not uncommon
4. The water depth is 200 feet 2 feet from shore - lots of boats get in trouble.
If you choose to go this way leave me a PM and I will chat with you about it on the phone. If I was not planning on crossing the pond this May I would go back to Newfoundland, I liked it that much.
If you do go, make sure you also plan to stop at St. Pierre and Miquelon. These are French (not French Canadian) islands off the southwest coast of Newfoundland. You will anyway as you will see when you do route planning.
As far as the Mississippi River is concerned it is pretty much a bummer for a sailboat. Unless you want to take the stick up and down a couple of times you will drop it in Chicago and put it back up in the Gulf of Mexico. Motor, motor, motor. Once you arrive in the Gulf you then need to get somewhere fun - that means crossing the Gulf to Key West. (I have done Mexico, Belize and Guatemala but again you need to have some significant cruising experience to deal with the adverse currents and the fact that the entire trip is on a lee shore. The political situation in these places is not very reassuring either.)