Where should i spend my summer?

i posted a thread a month or two ago about what boat should be my first.

here's a link to the thread; http://forums.sbo.sailboatowners.com/showthread.php?t=166981

The original plan was to get a small sailboat and float down the Mississippi. i ended up finding an O'day 25. http://i.imgur.com/GfN0D4m.jpg A little bigger than what i was original looking for, but thanks to a couple of you i was able to find it for a good price. my next step is to plot a course, and figure out the details. any information i could get is appreciated. i have 4 ideas...

1. http://i.imgur.com/2pglq5a.png

- this was the first. straight down old muddy. From Still water to New Orleans. i had no idea what i was getting into, did not have a boat and had not talked to anyone about it when i thought of this course.

2. http://i.imgur.com/XnHdVW3.png the Ohio, Tennessee, Tenn-Tom, Black Warrior, Mobile River route.

- i soon found out that this might be a much better route. slower current, more places to stock up on food and water.

- although at this point i also thought i would have a smaller boat. much shallower, and lighter. also something that wasn't very nice and i wouldn't plan on keeping the boat once i got to the gulf. sell it for whatever i could, and fly back to Minneapolis.

3. http://i.imgur.com/kEdBDzK.png turn around at St. Louis and sail upriver back to Still water MN.

- Once i picked up the O'day 25 i thought i might want to keep it for a couple years. i also was worried that i might not be able to handle a bigger heavier boat in high currents. i thought about just going to St. Louis then turn around and go back up to MN. i would be able to hold onto my boat, and skip the extremely hot muggy weather of a southern summer.

- can you sail up stream from St. Louis to MN? how much slower would it be than going downstream?

4. http://i.imgur.com/1uMBmix.png

this is something i started thinking about once i picked up the O'day 25. i was told that if you haven't sailed before you probably want to stay away from the great lakes. however, with this route the weather wouldn't be so hot and muggy, i would still have my boat at the end of the summer, fishing and sailing on the great lakes would be more enjoyable than on a muddy river with barge traffic. the cities i would stop in interest me a lot more. also i have been in the south many times, but never to Canada.

i'm thinking i can stay in the bay near Duluth MN for a few days (check it out on google maps) until i get a good handle on sailing and navigating. then venture out into the open water. there are bays every 5-10 miles along the coast that i could park in every night, and i would only sail into the open water when the weather was good.

- i know locks are free on the Mississippi. are they also free on the great lakes?
-will i have trouble crossing the boarders between US and Canada as long as i have a passport? will they search my boat for liquor when crossing boarders?
-what are the currents like in some of those channels?

thanks for reading! again, any information you could give and any part of these routes would be very helpful in planning my trip.