Interesting idea.
If you don't want to just wing it, it seems like someone with good programming skill and access to a weather database would be able to model such a route quickly from recent historical data that includes mean wind vector.
Pick a start point, mean wind vector +/- a few degrees, and a distance range per day, then pick that day's endpoint city within your range.
Then repeat.
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WTB: Slingshot bicycle promotional documents (catalog, pamphlets, etc).
WTB: American Cycling May, Jul, Aug, Oct, 1966.
WTB: Bicycle Guide issues 1984 (any); Dec 1985; Apr 1994; May, Jun 1996; May 1997.
WTB: bicyclist May, Dec 1997: Jun-Dec 1998.
WTB: Bike World issue Jun 1974.
WTB: Litespeed head badge (circa 2000)