I have owned 3 motorcycles, a 1979 Sportster, a shop built custom 80" shovelhead, and a Valkyrie. All were ridden on long roard trips in the western United States.
My advice for the best way to do a 2-week roard trip is to decide approximately where you want to end up, pack your shit on the bike, and head that direction. Make all other decisions about how to get there, where to eat, what to see, and where to stay while your on the road. And take paper maps with you. They work a lot better.