A UNESCO-listed port stacked across 40-odd hills, held together by Victorian funiculars, street art and stray dogs. Scruffy, steep and endlessly photogenic.
Cerro Alegre and Concepcion
The heart of the UNESCO zone: murals on every wall, tiled staircases, and the 1883 Ascensor Concepcion, the oldest still running.
La Sebastiana
Pablo Neruda's tall, cluttered hillside house, kept much as he left it, with what may be the best writing-desk view in Chile over the bay.
Museo a Cielo Abierto
Open-air museum on Cerro Bellavista, where murals by leading Chilean artists are set straight into the alley walls and public stairways.
Ascensor Artilleria
A one-minute funicular up to Paseo 21 de Mayo, a promenade over the working port: cranes, navy ships and the full amphitheatre of hills.
Market seafood
Mercado Cardonal or the fishing caletas for machas a la parmesana, ceviche and paila marina at prices the hill restaurants cannot match.
Bus from Santiago
Frequent buses leave Santiago's Alameda terminal all day and take roughly two hours via the Route 68 toll road to Valparaiso's terminal.
Drive from Santiago
About 120 km and 80 minutes on the toll road, running straight past the Casablanca Valley vineyards, which makes a natural stop.
Ride the ascensores
Sixteen historic funiculars survive as national monuments and several still run, saving your legs. Otherwise it is colectivos and walking.
Best time to go
December-March for warm dry days, though the Pacific stays properly cold
Cheapest months
May-August: grey, damp and quiet, with the cheapest rooms of the year
Priciest & busiest
New Year, when the bay's fireworks fill every bed for miles around
Morning
Start low on Plaza Sotomayor by the navy building, then take Ascensor El Peral up to Paseo Yugoslavo for the first big view.
Late morning
Get lost on Cerros Alegre and Concepcion: murals, cafes, craft shops and staircases running off in every direction.
Lunch
A long seafood lunch on a hill terrace, or machas a la parmesana in the din of Mercado Cardonal.
Afternoon
Walk or taxi up to La Sebastiana, Neruda's house, then wind back down through Cerro Bellavista's open-air murals.
Evening
Sunset from Paseo 21 de Mayo above the port, then dinner and live music around Plaza Anibal Pinto.