Ushuaia, Argentina
Even though there are a few scattered villages a bit further to the south, Ushuaia is considered the southernmost (city) in the world. It was first the site of a prison established by the Argentine government. In fact, the prisoners cut the wood and built the town.
Those same prisoners built the railroad that is known today as the "Train at the End of the World," the southernmost railroad on the planet.
In addition to fabulous skiing and other winter sport activities, tourists come here to tour the local penguin colony, and to get up close and personal with the seals and Orcas (killer whales) in the Beagle Channel.