Sean...GO for it! Bur WHY would you want to do the Mississippi ? Other than the'little-boy' Tom Sawyer 'dream'. The Ol' Miss isn't called 'Old Muddy' for nothing! Plus, it lacks the interesting scenery that the Mobile River/TennTom offer.My partner and I started to do the Loop BACKWARDS but got carried away and never finished it. I am surprised that nobody has told you that Fred Myers mile-by-mile description of the  Loop from the Tennessee River south to Mobile...plus separate books on the other rivers. Don't start without them! Then Claiborne Young's wonderful books on the Pan Handle of Florida. So descriptive and full of historical info.Can't remember the exact date when we began our backwards Loop without digging up my log, but we were in Fairhope AL on the Easternshore of Mobile Bay on July 4. Planned to spend 2 nights there visiting my cousin, the there had been a LOT of rain up in the midwest and we could not begining going up the Mobile R. for THREE weeks! Fell so in love with this area I bought a house and moved here.There is just so many wonderful things to do and see along the way, and many beautiful ante-bellum towns to visit. Experiencing true 'Southern Hospitality' is one of those benefits. The first 4 days up the Mobile R. are an experience unparallelled! Absolute wilderness with just one very small dock along the way (Bobby's Fish Camp). There are 12 locks along the way with very easy to handle bollard and very friendly lock masters. Above each dam is a lovely lake. These locks are small compared to the big ones on the Ohio that hold 15 barges and the tow. Most of the pilots are friendly and helpful but they speak with  'Cajun' accent! When you anchor out it helps to check with the pilots to be sure you're anchored in a safe spot...they will  then tell other nearby boats to watch for us.As Joe Pica says, learning how to anchor on a river needs to be studied. you will probably want to choose a spot south of a curve where it'll be more shallow and probably a nice beach since the barges will have to swing out to the outside of the curve so you'll be out of their way. One hazzard anchoring on the river is that depending on the terrain, ie. limestone//slate bottom that has been scoured by current so finding a 'hold' can be hard...and by the same token, high water means lots of uprooted trees that hang up and become deadheads also known as 'anchor-eaters'!There are so many possible side trips to take, up the Tenn for a stop in Huntsville to visit NASA,  Chattanooga, Knoxville...or up the Cumberland to Nashville. Of course up the Ohio has many interesting places to visit...it has huge locks and interesting cities. Alan Lloyd has written extensively on the Ohio; Fred Myers has great info re the Ohio too as he has been a speaker on paddle wheel cruises going into Charleston WvaMost important is to watch for RAINS  from south of Lake Erie and the Ohio River because flooding will make it impossible to move against the current. My boat ran at 8kn and it was not possible to go against the current for 3 weeks! Demopolis is the 1st town you reach going up the Tenn-Tom and they keep the marinas south, posted about the current.I just had eye surgery so I hope this is readable!