In the summer the Kegen border crossing is open and you can research how to cross that border as there are a lot of posts here about it.
In the winter the fastest and easiest thing to do is probably backtrack to Almaty and then go to Bishkek and Karakol from there.
Almaty - charyn canyon - karakol
Re: Almaty - charyn canyon - karakol
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My 2012 overland trip from Tokyo to Istanbul: https://silkroadwanderings.blogspot.com
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Re: Almaty - charyn canyon - karakol
Yeah, Karakol-Charyn-Almaty is easy to do in the late spring/summer. I did it in September and it took some 6/8 hours.
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