Drake Olson on an unnamed glacier between Haines and Skagway. Olson has carved out a unique niche in Southeast Alaska ferrying adventurers into the little-traveled mountains around Haines. (Lex Treinen/Chilkat Valley News)

“I don’t really know where we are going,” said Drake Olson on a recent joyride shortly after takeoff from the Haines airport in his 1979 Piper Super Cub. “It’s all just one big feel out.”

It’s a clear blue day with only a…