Emiliana WineryWhen I was one of the five hosts of the short-lived "Confessions of a Travel Writer" on the Travel Channel, we took our viewers through Chile visiting several destinations, from Santiago to Patagonia.

The city of Valparaiso was by far my favorite, and I have returned several times since the show aired.

Valparaiso, on South America's Pacific coast and an hour's drive from Santiago, is a port town that's raw, edgy, beautiful and commanding.

It's easy to be inspired by the 42 hills that roll down to the mouth of an active, industrial port. Wooden homes of various colors nestle in their nooks on cliffs, cobblestone streets form a dizzying labyrinth and views are dramatic from any vantage point. Valparaiso's colonial city is a Unesco World Heritage Site.

I was amazed, during my most recent visit, at how little evidence I could see of the 8.8 magnitude earthquake that struck the city in 2010. Another quake struck earlier this year, less severe but still recording a powerful 6.7 magnitude, and didn't significantly damage the infrastructure.

About all that art

A mother lode of Chilean artists, both established and aspiring, set up camp here, including Gonzalo Ilabaca, a prominent painter who arrived almost 20 years ago.

Casa HiguerasIn addition to being architecturally engaging, the entire city is washed over by street art. The city is one of the few in the world where the street art is not only legal but often commissioned by the government. From concrete walls to wooden doors, from coffee shops to hinged gates, almost every structure has been dipped in vibrant colors with statement-making images and portraits that convey optimism.

There's even an open-air museum (Museo a Cielo Abierto) featuring prominent Chilean artists: a bit of a redundancy, since the entire city feels like an open-air museum.

One of Chile's most well-known literary figures, the poet Pablo Neruda, was also drawn to the coastal city. He set up a home at the top of a hill, which is now La Sebastiana museum, chock-full of Neruda's memorabilia.

Hotels are also taking a plunge in creative transformation, as reflected in the growing number of boutique properties.

In Valparaiso, Zerohotel -- a home from the late 19th century-- has been colorfully restored into one of the city's most art-centric hotel, boasting design-conscious features. The high ceilings enhance the natural light from original windows.

Perhaps the most popular hotel is Casa Higueras, a 20-room boutique property, also a historical home with commanding views of Valparaiso Bay from all guestrooms and an outdoor pool. Its Montealegre restaurant, touted by many locals as the best restaurant in town, has an outdoor dining terrace with the same sublime views of the hills and port.

And the wine

While art is the Valparaiso theme, wine tastings are as much of an attraction, with several top vineyards just outside the city.

Matetic Vineyards is a rustic getaway for those who like to sip and sleep: A former 19th century farm, the vineyard offers seven charming rooms at its base. Guests may take a dip in the outdoor pool, have a hearty meal in the restaurant beside a pond and ride horseback though rolling vineyards to the main area of production for tastings of carmenere, the flagship varietal of Chile. The vineyard sprawls over 25,000 acres of nature and offers outdoor activities such as bird-watching, hiking and bicycling.

Emiliana Winery BarrelsAt the Undurraga vineyard in the Maipo Valley, a cozy and romantic 100-year-old home is the perfect backdrop for weddings. The winery produces five varieties of red wines, all of which visitors can personally blend, cork, label and take home as souvenirs.

Indomita is one of Chile's heavyweights, and the brand is offered to passengers in LAN Chile's business class. In nearby Casablanca Valley, Indomita produces the Zardoz label, its top-of-the-line bestseller, made from grapes individually selected based on color and size.

For clients with ecology on their minds, Emiliana is a "green" winery that not only produces biodynamic, organic wines but also makes its own olive oil and honey.

Most visitors who tour Valparaiso also check out its sister city, Vina del Mar, a popular beachside resort town that is included in many cruise ship itineraries along the Chilean coast. Sublime beaches line a scenic road, which is peppered with stand-alone beach bars and markets.

For clients who want to ensconce themselves away from the beach crowds, the 65-room Radisson Aqua in Con Con is well-situated on rocky cliffs, with terrific views of the coast.

Adding to the hotel choices, the luxury boutique Palacio Astoreca is slated to open this month. The 23-room property, housed in a 1923 Victorian mansion now designated a national monument, has undergone a $5 million renovation and will feature the Alegre restaurant, led by a Michelin-star chef; a sleek spa; library; piano lounge; and, doubles and suites with terraces offering commanding views of the city and the Valparaiso Bay.

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