Punta Arenas, Chile
The southernmost city in the world is wedged between the Atlantic and Pacific Oceans on the Straits of Magellan. Punta Arenas serves as a launching point for expeditions to Antarctica and the wilds of Patagonia. Less adventurous folks can observe penguins in their native habitats at the Isla Magdalena and Seno Otway pinguineros; unique views of these waddling zoo favorites are an easy day trip away. In-port sightseers can ascend the Mount of the Cross for panoramic views over the city's colorful tin roofs to the Straits beyond and Tierra del Fuego on the horizon.