Hiking the 700-mile desert portion of the 2650-mile Pacific Crest Trail and hitchhiking around the United States. My skin was toasted that I didn't recognize myself in the mirror.
Backpacking trip throughout Japan during October 2003-January 2004. This isn't the typical train-riding backpacking, but the more enduring and liberating walking backpacking in an unknown country. I stepped off the plane with my backpack, a small phrasebook, and a fold-out map of the entire country. That was my prepration.
Hiking 800+ miles of the Appalacian Trail in 2004.
Biking 45 days mostly unplanned across North America. I ended up making it to Canada on my 1991 Bridgestone MB-4 mountain bike before catching the dreaded Greyhound bus home.