We made that trip coming up the rivers. Was a great experience! There are really 2 good cruising guides that you should get before you make the trip. I will find the names of them and let you know. Parts of the trip is boring but the barges keep it exciting. Just make sure that you contact the barges to see what they want you to do. They are very helpful and polite. When do you plan on making this trip? I almost forgot, you will need to unstep your for the trip thru Chicago, to get under the bridges. We have a ketch and we left it up until Portage De Souix, MI where we took it down. But the main mast was down for the whole trip starting at Mobile, AL. I think our Mizzen mast is roughly 35 feet and a few times it seemed iffy but we made it.