Check out greatloop.org for boatloads of info and faq, plus get some good
guidebooks (hint hint). You'll need to dismast for at least the first part of your trip, and you'll need to make sure you have enough
fuel for some of the longer stretches (and know which
fuel stops are still open this time of year). I'm agreeing with Pat above...trailer it down at least to the Kentucky Lakes, or better yet all the way to Mobile. Good luck, and have fun!