I worked on the Bering Sea side of the Alaska Peninsula for 10 summers and know the stretch from Port Heiden (Meshik R) to Cold Bay reasonably well. A fair bit of it is easy traveling, by AK standards, especially if you like beach walking (I don’t for days on end) or hummocks (compared to what, I guess). The north side is dryer, but coastal fog can be a bummer. The shield volcanoes are spectacular to look at when it’s clear, and there are lots of them.
Windy? Check.
No wind = bugs? Check.
Swamps or hummocks as only 2 surface choices? Check.
Variable weather? Check.
Bays with mud flats and endless sandbars? Check.
A bazillion bears? Double check.