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What are the most miserable travel vlogs?
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The Documentary 'Take Me To Pitcairn' fits the bill, I think. It's about a guy who really wants to visit a super remote island that's difficult to get passage to. Some private boat captain plans to go there, and signs up a bunch of tourists to fund the trip, including the filmmaker.
The whole trip is a giant shitshow from start to finish, and it's oddly compelling to watch.