Three cities provide insight into the culture and history of the South American country of Chile. The first city is Punta Arenas, located on the shores of the Straits of Magellan and the largest city in the region. Translated as "sandy point," the city is also known as "the city of red roofs" because of its colorful skyline. It is the southernmost city in South America and reached its golden age between 1850 and 1914 due to its wool and fishing industries. Its imposing cathedral on the central square and its 19th century architecture reflect this boom time, and the memorial statue to Ferdinand Magellan recalls its history. We visit a sheep ranch and a rookery to see the penguins before heading north to Puerto Montt, a fishing center settled by German immigrants in the late 1800s. Situated on a narrow coastal plain with the Andes Mountains in the background, Puerto Montt is a tranquil city with an active fishing economy, and its German heritage is evident in its alpine houses with balconies. It is the gateway to Chile's Lake District, and the active volcano Orsano dominates the area. We visit Orsano National Park and Emerald Lake created by the volcano and then travel north to Valparaiso, the most cosmopolitan city of the three. Once a major stop for ships traveling between the Atlantic and Pacific oceans before the Panama Canal was built, Valparaiso remains an important seaport as well as cultural center for the region. These three cities reflect the beauty, history, and culture of this vast country.