Pillbox Hike An amazing start to the day, the Pillbox hike is an upward climb of challenging cardio, depending on ones athletic ability. It pays to wear good shoes with grip, and not be scared of heights. The initial hike up, along the narrow and winding dirt trails, can be slippery and strategic. Upright tree branches and well established roots offer support along the way as you take calculated steps to the top. The rocky terrain is stable two-thirds of the trek making footing easier to handle. The reward for your efforts is the stunning vista at the top. A 360 degree view of mountains and turquoise blue clear ocean. One of many beautiful views that Oahu has to offer.