The only way for you to get across with a vehicle is to ship or fly it across the ocean.
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U.S. citizens do not require a visa as long as their length of stay in Ukraine is less than 90 days. Individuals requiring a visa must obtain it at a Ukrainian Embassy or Consulate before arriving in Ukraine.
If you plan to sightsee on your own, you must have a tourist visa. A visa is also required if you plan to depart Russia by another mode of transportation. Cruise ship passengers in St. Petersburg should seek assistance from the U.S. Embassy in Moscow for all emergency and passport services.
The Russian Tourist visa is usually issued for Single entry, for the cities specifically mentioned on the invitation/tourist confirmation, and the specified dates up to a maximum of 30 days stay. The period of stay cannot be extended in Russia. Embassy requirements and fees are subject to change without prior notice.
U.S. passports are valid for travel to Iran. However, the Iranian government does not recognize dual nationality and will treat U.S.-Iranian dual nationals solely as Iranian citizens.
Can you Take a Ferry Between Alaska and Russia? No, there are no passenger ferries that travel between legal ports of entry in Alaska and Russia. While there are plenty of cargo ships that make the journey across the Bering Strait, there are none that allow passengers or passenger vehicles.
Drive the Alaska-Canada HighwayThe most direct route to Alaska is to get on the Alaska-Canada Highway (AlCan) in Dawson Creek, BC. If you're coming from the middle or Eastern half of the lower 48 and you want to get there as fast as possible, head west in the US before going north to hop on the AlCan.