This article outlines the geographical challenges, water access issues, glacial crossings, and border uncertainties involved in completing a longitudinal end-to-end trek of Chile.
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Questions people asked
What are the geographical, logistical, and border challenges involved in completing a longitudinal long-distance trek of Chile (Chile på langs)?
Chile på langs would be brutal: about 4,000 km and three completely different problems.
North: the Atacama. Water is the crux, so you'd be relying on caches or road access.
South: fjords and the Northern and Southern Patagonian Ice Fields. Without crossing salt water you're probably on the ice for long stretches.
Bonus: part of the Argentina border on the Southern Ice Field is still undefined, just like the Alaska–BC border you mentioned. A purist "never leave Chile" walk can't be checked there.
The Greater Patagonian Trail exists, but as far as I know it crosses into Argentina repeatedly, so it's the Norway-via-Sweden version again. And a strict rule ends you on the mainland, because Tierra del Fuego is an island.