Valparaíso doesn't look like most cities. It's stacked up a natural amphitheatre of hills above Chile's Pacific coast, all faded Victorian mansions, rattling funiculars and murals splashed across every spare wall. It's colourful, steep and slightly chaotic — and where you base yourself matters more than in most places, because what looks like a short walk on the map can turn into a sweaty climb up staircases and switchback streets.

The classic first-timer base is the Cerro Alegre and Cerro Concepción pair, part of the city's UNESCO-listed historic quarter. Wealthy British and German immigrants built these hills up in the 19th century to escape the noise of the port, and the result today is European-style architecture, cheap public funiculars, viewpoints like Paseo Yugoslavo and Paseo Atkinson, and streets such as Pasaje Gálvez and Calle Templeman that are basically open-air galleries. You can walk to most of the main sights, the Fine Arts Museum occupies the 1916 Palacio Baburizza, and Puerto metro station is close by. Trade-offs: it's touristy, steep, and hotels cost more than elsewhere in town.

Hotel picks here span the budget range. Hotel Casa Higueras occupies a 1920s mansion on the cliff edge with harbour views, a garden pool and adults-only quiet, though rooms start around $330 USD. The writers' favourite, Fauna Valparaíso, has an artsy feel, a rooftop terrace and a proper Chilean breakfast spread from about $160 a night. At the bargain end, Casa Puente Hotel Boutique is a 1916 mansion doubling as a gallery — hand-painted walls, original Chilean artworks, a wine cellar and a plunge-pool patio — from roughly $100, with rare free parking.

If you'd rather skip the crowds, Cerro Bellavista and Cerro Cárcel offer a grittier, more residential scene. This is Pablo Neruda territory: his former home, La Sebastiana, is now a museum, and the Museo a Cielo Abierto spreads giant murals along the hillsides. The old prison has been reborn as the Parque Cultural de Valparaíso, hosting exhibitions and theatre. Hotels are cheaper and the atmosphere more local, but restaurants are thinner on the ground and the hills go quiet after dark.

The standout here is Hotel Winebox, built from upcycled shipping containers with pallet furniture and wine-bottle lamps. There's a working winery on site — visit during harvest and you can help with the winemaking — plus kitchenettes, wine-stocked minibars and free breakfast.

Two practical notes worth heeding. First, book three to four months ahead; the good properties sell out well in advance and last-minute options tend to be overpriced. Second, skip the rental car — driving Valparaíso's steep cobbled lanes is a headache and parking is scarce. Funiculars, buses and taxis cover the rest, though check funicular schedules on the day since closures happen.

In short: first trip, stay on Cerro Alegre or Cerro Concepción and pay the premium for location. After that, or on a tighter budget, Bellavista's murals and container hotels deliver plenty of character for less.

Story via Destinationless Travel.