New answers tagged alaska
Alexai Point Army Airfield is the airfield used in World War 2. The Airfield is abandoned and can be visited without permission having closed in 1946. Further west, he naval airfield that became "Naval Air Facility Attu" is also closed but can be used for emergencies, however I suspect that you are more interested in Alexai Point
There isn't anything special about your itinerary - travelling through Canada is the same as flying over water to other non-mainland US areas. For the US part of the question, see the related questions on the right (e.g. Can we get a new visa waiver in Canada, for Alaska, when our old one expires in the US?). To summarise, your VWP visa clock starts ticking ...
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