Valparaiso is the second biggest city in Chile and serves as Chile’s main port, about 72 miles northwest of Santiago. Surrounded by hills and the Andes in the back, Valparaiso was recently declared a World Heritage Site for its fine architecture and most definitely a nice place to stop while visiting Chile. However, one must be warned, Valparaiso has a reputation as being a rustic and working-class city. For instance, its neighbor, Vina del Mar, has the reputation as the glamorous outpost for casinos and nightlife. Meanwhile, Valparaiso is a mix of old colonial architecture, active harbor sights, and a hodge-podge of quick and hasty construction. Thus, while the downtown has more romantic historic streets, its hills are covered with vast stretches of inconsistently laid-out houses which clearly lack city planning. Still, the 350,000 residents are very proud of their city which is the largest sea port for Chile; it is appropriate that Valparaiso is home to the country’s Naval College. Even the homes that seem to be unstructured have history; locals claim they are made of discarded sea-faring equipment.   Though the city is long past its golden area, it is good to visit to get a real feel of ‘working’ life in Chile, as well as to enjoy first-class seafood restaurants, fresh marketplaces and quaint Viennese café shops.