Free Tour of Valparaíso's Funiculars & Promenades

Valparaíso once had around thirty ascensores climbing its hillsides; a little over a dozen still run today, and this two-and-a-half-hour walk from Plaza Aníbal Pinto rides several of them, tracing how locals have moved between el plan, the flat port district, and the amphitheater of cerros above since the 1880s.

Between funicular rides your guide leads you along the paseos — the panoramic walkways that edge the cliffside, including Paseo 21 de Mayo on Cerro Artillería, where naval cannons face out over the working port and the whole bay opens up below. Expect plenty of stops for photos of the mismatched, brightly painted houses stacked one above the other.