Santiago (Valparaiso), Chile
A bay bordered by steep hills, stately old Victorian homes, cable cars - no, it's not San Francisco, California. Welcome to Valparaiso. Populated in 1536, and named after the birthplace of conquistador Diego de Almagro, Valparaiso is Chile's oldest city. It is also the gateway to Chile's central valley and the capital of Santiago. With a population of over 5 million people, Santiago sprawls at the feet of the snow-capped Andes. The Maipo Valley, Chile's internationally renowned wine district is a short drive to the south.