I read a book called A Walk Across America in college, by Peter Jenkins. I liked the idea of traveling under my own power, but I didn't want to spend years walking. I kept when I got my driver's license, and I was bike commuting in NYC at the time, so biking was a natural fit.

I was teaching at the time, so the first summer without any obligations I rode across the northern US. Then I rode across the southern US the next summer. I loved it, and wanted to live outside for all the seasons. So the next year I quit my job and circled the continent: Seattle to Maine, down to Florida, across to California, then up to Alaska. I moved to Alaska a few years after the trip ended and spent 20 years there. We moved to North Carolina last year, because dark southeast Alaskan winters were getting old, and all our family is on the east coast.

I'm grateful to have had the opportunity to do that trip in the era of paper maps, and truly being out of touch for so much of that time. It pushes you to meet so many new people in all the places you visit, instead of staying in constant contact with people you already know. It was also nice to not see satellite imagery of the road ahead. Every day was a surprise. :)

I did write a book, The Road to Alaska: https://www.amazon.com/Road-Alaska-Eric-Matthes-ebook/dp/B07...

One of my claims to fame is writing one of the best-selling Python books of all time (Python Crash Course), and one of the lowest-selling travel books of all time. :)

I rode a bicycle from Canada to Mexico (in about a month) with a close friend. We bought a book called Bicycling the Pacific Coast (before smart phones).

I had a cheap $150 univega bike and my friend had a $3000 cannondale. His broke mine didn't :)

We were amateurs. We hitchhiked to a bike shop near San Francisco to fix it. Had some saddle bags with our tent and sleeping bag, clothes and water.

It's very doable. Hardest part is just showing up.