My dad has always been an avid motor vehicle fan. Even in my earliest memories, he's covered in grease and oil, sticking out halfway from underneath a car. It only makes sense to make this post under the tag of the week.
My dad's parents died when he was young and finishing college around 1970, leaving him with an inheritance split among 3 brothers. He took the money and decided to use it to travel by motorcycle throughout Eurasia. He, and at times the middle brother, traveled the route known as the Overland Asia Hippie Trail, beginning in Europe and traveling out to South Asia.
Things that he did on this adventure:
Visited 10+ countries
Learned Vietnamese
Kicked a taxi in Turkey when the guy almost ran him over
Caught up with his brother from thousands of miles away via word of mouth from other travelers on this same path (my uncle got sick or bored or something so he peaced out for a little while)
Wore pants made of rice flour sacks and sported a rad hairdo and mustache dup 
Was photographed in front of the Khyber Pass, a place I can only dream of visiting 
* eventually moved to England, ran out of money, and moved to California where he opened his own junkyard before working in tech
He's fairly anti-motorcycle these days, but I think that's because he lost too many friends to road accidents.
The first time I had ever heard of this story was when our synagogue was featuring notable members in its newsletter in the late aughts and, as a teenage girl, was SHOCKED to learn that my dad had once been cool. I wish I could find the full story to share with you all, but the digital archive is incomplete, so I recreated it as best I could from memory.
Bonus dad picture: 
ETA: I think it was also on this trip that my dad met with the Dali Lama and received a blessed scarf from him. That's across the country though otherwise I would share pics.