I've riden passenger with my Dad for years but cross-country trips are entirely different. My parents were riding buddies up until my stepmother passed of cancer last year. Because of the medical expenses, he was sure he would have to sell his bike. Long story short, I promised to go on a trip with him (either Rolling Thunder or Sturgis) if he kept the bike for at least a year...it always helped him clear his head in the past. I won't ever be the same...now I get it...the feeling of putting your life in God's hands as your moving at 95 miles an hour through the mountains he created. Every small, insignificant thing you worried about the day before doesn't matter any more. You're back to being a small part of something much greater. During the 4 days of our trip from Milwaukee to Washington D.C. it was an emotional rollercoaster from "Wild Hog" excitement, to crash worries, to pride from riding with so many veterans (Dad is a Vietnam Vet '66-'69).
That trip really helped both of us clear our heads...I'm now considering buying my own bike...I've had my bike license for almost 10 years but my ex never wanted to buy one.