Because of its photogenic delights, Valparaiso is probably the most visited Chilean town outside Santiago, as it should be. The metro area, second-largest in Chile, also encompasses the much-less-gritty resort towns of Viña del Mar and Reñaca, all within easy daytrips from each other. At about the same latitude south as Los Angeles is north, Valparaiso is famous for its beautiful setting with the stunning bay surrounded by hills very irregularly cluttered with often interesting buildings of all shapes and sizes, reachable by more than a dozen old-fashioned funiculars. All this can make for some great travel photos, the Mediterranean type climate is sunny and the light terrific, coastal fog/cloud seems less of an issue here than is the norm on the Chilean coast. The highlights of Valparaiso are the (UNESCO listed) funiculars and the photogenic hill neighborhoods and bay views they access. The funiculars are surprisingly many, all of them unique, interesting, rickety affairs, though sadly used largely by tourists these days (locals take buses). Valparaiso has been in near continuous decline for over a century and it very much shows. Middle class has mostly decamped to Viña and beyond. As a major port, Valparaiso used to have a somewhat rowdy reputation reportedly, but things are clearly quite a bit duller these days and while the lower town has people milling about during office hours, otherwise you may have a hard time locating lively areas anywhere (there are some very small pockets scattered about).