Cold Bay Alaska is the cloudiest city in Alaska statistically (averaging 304 overcast days each year) but the population is less than 100 because I think it is mostly a military base in the Aleutians. But any city on the Kenai peninsula has a lot of clouds, as do cities like Juneau in the Southeast. Seward is usually cloudy.
Just get a map of Alaska and pick a city, there you go, you just found the city you were looking for.
Well I am From INDIA and i know which is the cloudiest city in ALASKA.. The cloudiest city is Juneau
I would say anchorage