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I'm contemplating an overland advernture trip starting in Southeast Asia (possibly Malaysia or Singapore) to South Asia, ideally to the Hunza Valley in Pakistan, but just getting as far as any entry point to India, Nepal, or Pakistan might suffice.

I see there are some mountains in my way. There are also some countries not easy to pass through, like Burma (Myanmar), some borders which might not be open, or at least not to non-locals (I have an Australian passport), some conflict zones, and the non-triviality of entering Bhutan.

So it seems there are potentially routes both south of the mountains through various countries, depending on what's possible after taking into account the above; and north of the mountains across an apparently large expanse of China, about which I don't know much. (How stupid of me! That area is Tibet, which requires special permits to enter so also may not be too easy...)

Which of these routes is the more possible, safe, and/or affordable?

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Since you consider Myanmar difficult, the best route would be:

Malaysia, Thailand, Laos, China. There, avoiding Tibet and Qinghai completely, going through Yunnan, Chengdu, Xi'an, Lanzhou, Urumuqi, Kashgar and from there into Pakistan. The interesting part here is that you basically travel along the silk road, which is very interesting. I did that 2 years ago, it was fascinating.

If you think Myanmar is fine (I would think so), it is obviously Thailand, Myanmar, India (possibly Bangladesh) and then Pakistan.

I would consider the first route as more expensive, but more safe in terms of health risks and road safety. Since you will pass less through tropical climates, there are less risks to my experience on many levels. If you take public transports in China you might have a much more comfortable experience than through Bangladesh.

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    Actually Burma is the place I am most interested in in this region but [according to a previous question], I can only cross the border at Thailand or China, must exit at the same point I entered, and can only stay for 24 hours. Flying in and out would break my overland criteria though. Also I thought that either the border was closed with India or it required a special permit as well as an Indian visa that way.
    – hippietrail
    Commented Apr 8, 2013 at 7:02
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    The only border crossing accessible to foreigners is at Wagah Point (in Lahore, the corresponding city is Amritsar in India). So going north and then back south is not an option anymore for foreigners.
    – Burhan Khalid
    Commented Sep 8, 2016 at 4:59
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As you have already realized, the Himalayas form a giant fence between South Asia and China and the small gap between the mountains and the Bay of Bengal is plugged by Myanmar.

Getting into Myanmar nowadays is reasonably easy, crossing at Mae Sot or Mae Sai, but leaving is a problem. You need a permit from the Burmese government to leave at Tamu (this company claims to be able to get you the paperwork in a month or so), and you need both a visa for India and a permit from the Indian government to enter at Moreh.

It's not impossible though.

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