Originally Posted by DiabloScott

There is no way these two guys are going to treat a 2-day, 180 mile ride like what all of us think of as a race.

What's important is that the OP wants to "beat" the other guy and his more modern bike. The way to do that is to have lots of smaller little competitions, in between many miles of riding together in comraderie.

First one to the top of this hill up here.
Sprint to that telephone pole.
Time trial to the next rest stop.


It'll be obvious who the winner is.