I visited this WHS in 2023 and explored this huge urban sprawl of a seaport city over 3 days. I'm usually not a keen fan of graffiti art but nowadays in Valparaiso it has become part of the city's identity. Whether you like it or not, the graffiti art is constantly changing, so on average every month or two some graffiti you might like or dislike will disappear and change.

The geographic location on steep hills overlooking the Pacific Ocean and the different nationalities of its inhabitants have led to a distinct and innovative urban landscape. The city centre is by the port where you'll find Plaza Sotomayor consisting of buildings from different periods that merge into one big area, with the monument of the heroes of Iquique, one of the oldest hotels in the city, the pretty Edificio de la Intendencia de Valparaíso, the odd modernised and controversial Edificio CSAV (a leading shipping company with a skycraper-like glass extension), and at the northeastern side of the square there are two similar towers, which create a sort of gate entrance to the port from the city.

The steep hills fully covered with colourful buildings, more or less legally built, reminded me a lot of Guanajuato, Mexico. Although I drove in and out of the city a number of times, the best way to explore this city is on foot or by very cheap public transport. Although the 16 remaining ascensores can literally be translated as elevators, only the Ascensor Polanco is a truly vertical elevator; the rest are slanting funiculars and are very handy shortcuts up and down the different areas of the city.

There used to be clear signposted heritage trails but most have disappeared under layers of graffiti. However, I managed to find a couple of rusty plaques with the UNESCO symbol on the floor close to the Lutheran church and the Cathedral of St. Paul, Paseo Atkinson (nice views from here in the morning), Paseo Yugoslavo with the beautiful eclectic Art Nouveau Palacio Baburizza, Paseo Gervasoni, etc. I always walked around with my camera strapped to my neck and although many locals (taxi drivers, shop owners, locals, police) warned me about pickpockets and to stay away from shady areas, I never felt in danger or at any risk. Perhaps I was lucky or else the friendly locals were being overprotective. The most shady area perhaps was around the Iglesia de la Matriz.

Valparaíso played an important geopolitical role in the second half of the 19th century when it served as a major stopover for ships traveling between the Atlantic and Pacific Oceans by crossing the Straits of Magellan. It experienced rapid growth during its golden age, as a magnet for European immigrants, when the city was known by international sailors as "Little San Francisco" and as the "Jewel of the Pacific". The golden age of Valparaíso's commerce ended after the opening of the Panama Canal in 1914. Notable buildings from its golden age include Latin America's oldest stock exchange, the continent's first volunteer fire department, Chile's first public library, and the oldest Spanish language newspaper in continuous publication in the world, El Mercurio de Valparaíso. Most of the buildings near the port though are crumbling or mere facades with supports and have never really recovered from the 1906 and 2010 earthquakes.

Apart from exploring the city on my own, I also joined a morning walking tour organized by Tours 4 Tips named Offbeat Lato B de Valparaiso. I really enjoyed the frank and not politically correct tour to places beyond the obvious highlights of Valparaiso mentioned above (they also have another walking tour for that if you prefer). The recurring theme of most graffiti art are figures with staring eyes, an obvious reference to the 2019-2020 Chilean protests characterized by widespread eye injuries, including many globe ruptures ("exploded eyes"), among protesters as result of Chilean riot police's use of rubber bullets and tear gas grenades. Another interesting place to visit was the Parque Cultural de Valparaiso which was the city's former public prison where Pinochet's victims were once tortured.

For the foodies, Valparaiso has great dining options with a variety of good restaurants and street food (don't miss excellent completos (fully loaded hot dogs) and Piscola, Vino Navegao or the local Valpomule). Valparaiso's seaside sister town of Vina del Mar is also worth visiting, if only for a quick peek at the sea lion colonies basking in the sun there and the original Rapa Nui moai in front of the Museum of Archeology and History Francisco Fonck.