Early in my airline career in the late 80’s, I was based in Guam flying 727s as a flight engineer. We flew to lots of small islands and also to Japan, The Philippines, Papua New Guinea and Hawaii. Pilots from other airlines were welcome to fly for free in our cockpits.
There was a pilot for, I think, Qantas or maybe Air New Zealand who would ride our Jumpseat back and forth from Guam to various places in the South Pacific during daylight hours. He flew with me from Guam to Manilla a few times and I heard he flew to Port Moresby sometimes and also to other islands. He always flew both ways with us and never stayed.
His son was sailing a smallish blue water sailboat in the area and had not been heard from for months. This poor guy spent his days jumpseating on airliners and staring out the cockpit windows looking for his son’s boat.
His demeanor in the cockpit was respectful and quiet. He didn’t say much and leaned into the side view window and never accepted a drink or a meal lest he miss a moment. He spent over 3 hours on each leg with intense focus on the endless water. At the end of the flight, he seemed tired and his voice was lower and softer.
I don’t know when he gave up. Deep down, I’m sure he knew his son was long gone. The hopefull futility of his lonely flights were heartbreaking to me.