Little Diomede Island

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For starters, the nearest land mass is Russia: The slightly larger Big Diomede Island is just over two miles away, within eyeshot of the Alaskan villagers.

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Village permission should be sought (via letter) prior to visiting along with arrangements for transportation, housing and food. Self sufficiency is advised. Transportation to and from the island is restricted and expensive.
My background is someone who has traveled to Little Diomede. The first step would be to talk to the school about renting a place to sleep. ¶ Second, you would need to fly to Nome on Alaska Air. There is a helicopter service to Diomede. You will probably fly to Wales, Alaska and catch the helicopter there. People are correct that air service is normally once a week. If you go to Diomede you need to plan to stay a while.

Wikipedia

Little Diomede Island (Wikipedia) Little Diomede Island or Yesterday Island (Inupiaq: Iŋaliq, formerly known as Krusenstern Island, Russian: остров Крузенштерна, romanized: ostrov Kruzenshterna) is an island of Alaska, United States. It is the smaller of the two Diomede Islands located in the middle of the Bering Strait between the Alaska mainland and Siberia.

wikivoyage

Little Diomede (en.wikivoyage.org) Little Diomede is the smaller of the two Diomede Islands that lie in the middle of the Bering Strait. Little Diomede is the westernmost part of Alaska while Big Diomede, only a few km away, is the easternmost point in Russia.