Absolutely impossible to drive across the Bering Strait, except in snowmachine, and on that very risky. Don't even think about it.
It might be possible to ship a bike to Magadan or Khabarovsk by Alaska Airlines. They used to have flights there from Anchorage, I don't know if they still do. But Alaska's website is easy to find.
Charlie
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Unimog U500 w/Unicat
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