US citizens traveling between Ukraine and Russia

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Your brother does not need to worry about crossing the borders between these countries. But it is worth considering that the entry-exit to the Crimea should be carried out only from the Ukrainian border.

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  1. There should not be any problems crossing Russia-Ukraine boundary.
  2. Except if you visited Crimea previously by going in from Russia. Ukraine normally have no ways of knowing that you did, but if they do, there's threat of legal action or they will just deny entry.
  3. You can in theory visit Crimea from Ukraine as other answer suggests, but AFAIK they will not let you cross border to Crimea. They only let in Ukrainian citizens with urgent needs or so I have heard.

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There are currently no direct flights between Russia and Ukraine. You'd need to factor that into consideration.

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