1. San Jose, CA -> St. Louis, St. Louis -> Seaside, Oregon (followed the Louis & Clark trail as closely as possible), Seaside, Oregon -> Vancouver Island, BC, Vancouver Island, BC -> San Jose, CA
Did it in about two and a half weeks.
2. San Jose, CA -> Yuma, AZ -> Deming, NM -> San Antonio, TX -> Memphis, TN -> Louisville, KY -> Cleveland, OH
Did this one in about a week.
Now... on my Buell.... the longest I've gone is Cinci, OH to Cleveland, OH. I'm not insane enough to ride those big ones on my little Dixie!