When I quit my job and went travelling I used this framework:
1. Go via land. You see everything in between all the places you should see as a tourist. You immerse yourself in how a place actually feels. You meet people who aren’t just trying to extract money from you. I cycled, because I like cycling, but any form of transport works.
2. My algorithm was something like “Go east. Stay somewhere if it’s interesting, until you get bored. Continue going east.” I didn’t have a fixed itinerary, but I did have some framework.
That was the basis of it, I think. I cycled from London to Italy, stopped for a while in Italy, cycled on to Greece, then fell in love (with the place and somebody in particular). I met some of my best friends, worked on side projects, volunteered for charities, and ended up staying there for several months. I skipped forward to India on a plane, cycled across India, then returned back to Greece.
My partner in Greece wanted to visit the Middle East and Central Asia, but she wasn’t quite as excited about cycling through the desert as I was, so we bought a van and drove — to Central Asia, and everything in between.
My framework worked extraordinarily well. If I have one regret, I think it was not making an effort to interact with more people. You do that a lot more naturally when travelling by land, but you still need to put in effort to make it happen.
For example, I was up late in a bar in an Italian village, and met one of the locals. It was a long cycle ride back to the place I was staying so he offered me his spare room. Turns out he lived with his parents and the next day his elderly Italian mother cooked us pasta for lunch. Possibly one of the best meals of my life.
I wish I had done more of that. Just hanging out in bars and making friends. And not tourist bars — real bars. Knowing the local language better would probably help.