One doesn't need to be rich to go sailing, it's sufficient to be crazy. Like, Jarle Andhøy went from the arctic to the antarctic almost without any funding and with a boat he basically got for free; he's not alone going out for such adventures. Even though this guest harbour costed us 20 EUR (it would have been cheaper with a smaller boat), in this review I'm also covering the anchorage, it's totally for free to use.
I'd also recommend to follow @movingman, he left from the UK with almost no money at all, only a van - and hasn't returned since.
Though ... you are probably right, things are probably much harder in the third world, like getting hold of a working van or a sailing boat for free or almost for free is probably not an option, and getting a passport or visas can be pretty hard. Living the life of @movingman (i.e. searching garbage bins outside shops and finding perfectly good gourmet food) is probably only possible in the rich world. Still, I believe opportunities can be found anywhere. Quite much work nowadays is purely intellectual and can be done from anywhere, with cryptocurrencies it's also possible to get paid instantly across country borders.
Thanks for inspiration....my friend