You could ride this one September 20-27, come home & rest and then do the Natchez Trace with Barbara in October.
Joan Gilley & friends rode this on their own in ‘96 and I have the pictures to prove it. It looks like a great ride with some good features. Like all meals provided, bike support, luggage transport, 335 miles with 50-60 mile average per day and $2300. It is also driveable so can take your own bike, about 7 hrs away.