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Me and a group of friends did it about 10 years ago. Had a blast despite having an accident the first day and having some horrible dripping road rash the rest of the trip. It was four of us and another friend that was recently divorced and just wanted to drive his RV. So we had a nice place to crash every night. If you can ride 10-15 miles you can do this. All manor of bikes and fitness levels do it. Yeah there are the racer types, but thats a minority, and you never see them because they've got to be in front.
FIgure out where you will sleep and have a good time. Drove past a lot of corn fields. They love corn in Iowa. The sleep location is the hardest part.
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