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Chie’s capital city of Valparaiso, once known as the “Jewel of the Pacific,” has not lost its glimmer in the eyes of travelers and expats. Although the historic town is actually a UNESCO World Heritage site, its constant evolution of architectural styles makes it a hodgepodge of history rarely seen among such sites. The eclectic clash of culture is as mixed as its buildings, as is the wide array of entertainment available that line the hilly cobblestone streets. The white-sand beaches of the coast lend a beautiful backdrop for funky pubs, luxury casinos, restaurants and wine bars that provide a taste for every palate that visits this port town along Chile’s central coast. For more on this continue reading the following article from International Living.

For many years it was the “Jewel of the Pacific.” Even today, long after the Golden Age of the port city has passed, the brightly-painted hillside houses, cobblestone alleyways, and winding streets of Valparaíso, on Chile’s central coast, are among the country’s most enchanting finds.

Just 75 miles northwest of the capital, Santiago, “Valpo,” as the locals call it, was once an important stopover for ships traveling from the Atlantic into the Pacific Ocean. Immigrants from England, Italy, and Germany settled here and left their mark on the city’s architecture and culture. But with the opening of the Panama Canal the port declined and the wealthy families left.

The historic town—a UNESCO World Heritage site—is a creaky, hilly jumble of stone, stucco, and wood-framed homes, reflecting Valparaíso’s stop-and-go historic progress. Few signs remain of the Spanish traffic of the 1500s, nor of the 19th-century industrial boom. Instead, due to an earthquake in 1906, the town is a hodgepodge of 20th-century styles.

While the civic buildings are Italianate designs of stone, private homes resemble San Francisco’s Queen Anne style, interspersed with simpler Colonial Revival cottages.

And although, like San Francisco, it has a mild climate, we arrived during stormy weather. After four months living in Santiago, we were leaving Chile, and this was our last chance at an exploratory trip to the coast. We weren’t going to let the rain stop us.

Meandering through the port’s steep cobbled passageways, we found a popular lookout point on Paseo Gervasoni. From here you can see the sweep of the bay and ships bobbing at anchor. The nearby Art in Silver Workshop is stuffed with sleek designs in silver and local lapis lazuli, and the quirky Casa Mirador de Lukas is worth a visit to find cartoons and drawings for sale.

We stopped for a leisurely lunch in The Brighton, a funky hotel and pub with a nice patio overlooking the port. We relaxed with a bottle of wine and a plate of cold cuts for under $20.

When the wealthy left Valparaíso they didn’t go far; just three miles down the coast is Viña del Mar (Vineyard by the Sea). And that’s where we headed next. Viña is a newer town and a popular center for summer and weekend tourists from Santiago and beyond.

Its white-sand beaches are where Chileans come to be seen. It’s also home to the oldest casino in Latin America, the Municipal, founded in 1930, and there’s good shopping and a good mix of restaurants. We headed to the Enjoy Casino in Viña, which is a big draw since there are so few gambling establishments in Chile. In this spacious, luxury casino, the atmosphere suited us both. I opted for a glass of delicious local wine, my book, and a comfortable perch.

My husband Tom, meanwhile, played poker. After a couple of hours, Tom had won enough to pay for our Hotel Da Vinci back in Valparaíso and the return taxi. With the winnings, I guess we could have afforded the Enjoy Casino rooms (from $350), but we were happy in Valpo.

The next morning, we took a rental car (about $145 for the weekend from Europcar) north toward the village of Zapallar to visit more off-season coastal areas. Passing Viña we enjoyed a familiar drive through Reñaca, a popular beach area, on our way to Con Cón, a funky little resort town where we’d spent a week in the sun and surf earlier in the year. Wild waves four or five times as big as anything we’d seen on our last visit came crashing onto the rocks interspersed along the sandy beaches. We pulled over to watch sea lions battling them…

This article was republished with permission from International Living.