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115km (71 miles) NW of Santiago; 8km (5 miles) S of Viña del Mar

Valparaíso is Chile's most captivating city, and, accordingly, it is the most popular coastal destination and an obligatory cruise ship port of call. During the 19th century, Valparaíso ranked as a port town of such wealth that few others in the world could compare, but in the years following the completion of the Panama Canal, Valparaíso sunk into poverty. Like a penniless aristocrat, the city clung for decades to its glorious past, yet only traces of the architectural splendor and riches the city once knew could still be seen. Today, especially on hills such as Cerro Concepción and Cerro Alegre, the city's run-down buildings are experiencing a rebirth. With so many gourmet restaurants and boutique hotels opening at such a fast pace, Valparaíso is quickly becoming the choice destination for dining and lodging on the coast. The historical importance of this city, paired with the vibrant culture of local porteños, is far more intriguing than Viña -- a reason why UNESCO designated Valparaíso a World Heritage Site in 2002.

Much like San Francisco, the city is made of a flat downtown surrounded by steep hills, but unlike that city, the irregular terrain in Valparaíso presented far more challenges for development. The jumble of multicolored clapboard homes and weathered Victorian mansions that cling to sheer cliffs and other unusual spaces are testament to this, and you could spend days exploring the maze of narrow passageways and sinuous streets that snake down ravines and around hillsides. Given the lack of towering high rises on the hillsides, the city is frequently described as "stadium seating" -- providing breathtaking views no matter where you are.

Valparaíso has spawned generations of international poets, writers, and artists who have found inspiration in the city, including the Nobel Prize-winning poet Pablo Neruda, who owned a home here. The city is also known for its bohemian and antiquated bars that stay open into the wee hours of the morning.

But the real attraction here is the city's streets, where you can admire the angular architecture that makes this city unique, and ride the century-old, clickety-clack ascensores, or funiculars, that lift riders to the tops of hills. If you're the type who craves character and culturally distinctive surroundings, this is your place.