Valparaíso

About a 90-minute drive west of Santiago lies the coastal town of Valparaíso. Because Santiago sits inland, this city on the sea emerged in the late 1800s as Chile’s primary shipping port, and benefitted financially from an influx of wealth. Built on 45 hills, the town’s Victorian houses—painted in every color of the rainbow—create a picture-perfect setting and extraordinary views of the coastline and dockyards. The colorful architecture and hillside setting, along with its laid-back nature and numerous cafés and restaurants, combine to make the city feel like a South American version of San Francisco. Little has been changed or renovated since the heyday of the 19th-century (once the Panama Canal was completed, Valparaíso’s ports were not as crucial) and the town is charming, in a scrappy kind of way. Walls are covered with beautiful and vibrant graffiti, representing everything from pithy cultural references to what could be considered works of art. As a lively student town, Valparaíso has a fun and energetic nightlife. In reply to the question of “when do bars close?” most locals will answer, “when the candles burn down.”

Funiculars, dating back to the 1880s, still carry people up and down the steep hills, though the women of Valparaíso are rumored to have “the most beautiful legs in the world” from the constant exercise. Strolling the rambling pathways of Valparaíso, breaking for lunch at one of the lauded restaurants like Pasta e Vino (Calle Templeman 352, Cerro Concepción; 56 32 249 6187), is a lovely way to spend a morning before an afternoon of wine tasting in the nearby wineries. If visitors would like to spend the night in Valparaíso, there is the Relais & Chateaux property Hotel Palacio Astoreca (hotelpalacioastoreca.com), a boutique hotel with stunning views of the coastline and a magnificent restaurant Alegre, headed by ex-El Bulli chef, Francisco Araya. It is housed in a renovated Victorian mansion and sits across from the also newly renovated fine arts museum, Museo Baburizza (www.museobaburizza.cl). Pablo Neruda’s home La Sebastiana (Ferrari 692; 56-32-225-6606), with its boat-like structure and dazzling views of the bay, is a perennial favorite, and is situated on Cerro Bellavista.