Valparaíso, Chile’s main port city, rises from the water into steep hills laced with staircases and winding streets. Generations of poets, mariners, and adventurers have passed through. While the city has some of Chile’s best dining, the streets retain a Bohemian vibe. In the course of a weekend, visitors can stay at a high-ceilinged bed-and-breakfast, ride 19th- century funiculars up and down coastal bluffs, travel back in time at Pablo Neruda’s home, and relax over local microbrews. Just watch out for drunken sailors—Valparaíso’s port still welcomes vessels daily. —Steven Bodzin

This appeared in the November/December 2011 issue. Photo by Roberto Ruiz.