I've relatively little experience of travelling in the Americas; I've always wanted to go to places with a bit more history and culture. Not sure if you are looking for Americas specific replies, but here is mine after years of travel in Eurasia (on 4 wheels).

When I was 25, I left my native UK in my Toyota Hilux. I'd been working and saving for three years, had plenty of money in the bank and no commitments whatsoever to worry about. I left in May 2007, thinking that I would be away for 12 to 18 months. It turned out to be 55 before I came even close to the UK again.

I was travelling pretty much the whole time around much of Eurasia, but very slowly. Where I really fell in love was Pakistan. I passed through twice, then decided to go back a third time, stay with a local family and volunteer in a school. I felt more at home in Pakistan than anywhere else I have ever visited / lived, I loved almost everything about it.

If you are interested about my experiences there, I would recommend this article on my website:

Stage 15 – Pakistan: Interlude | EurasiaOverland

The key is to interact with local people. I see a lot of overlanders (on four and two wheels) whizzing through countries in something like a bubble, minimising their interaction with locals and their culture, and I wonder what they are getting out of the experience. It's no coincidence that cyclists (as in pedal bikes) tend to write the best travel blogs, they generally have far more interaction.

Coming back to the UK, I got into a good university and then a 'good' job, but where I currently live (sorry if you are Dutch) in the north of the Netherlands is the most boring place I have ever been and I'm itching to leave and do something like this again. Luckily the long Dutch holidays allow me to do a 6 to 8 week trip each year, which is better than nothing!

Good luck!

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EurasiaOverland a memoir of one quarter of a million kilometres by road through all of the Former USSR, Western and Southern Asia.