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Built in the 1920s by a Croatian businessman, Palacio Astoreca underwent two years of refurbishment and restoration before opening its doors as a boutique hotel in 2012. The work was carried out to a meticulous degree, maintaining the original parquet floors, and adding splashes of color with art deco furniture and modern art, including one piece by Switzerland’s Frédéric Clot. The stucco-and-brick mansion rises up from the streets of Chile’s port city, Valparaíso, like a piece of red-and-white confectionary.

A statement staircase winds up to the 23 rooms, some of which have stand-alone bathtubs. And the basement level is home to a small spa with an open-air, wood-fueled hot tub set alongside a living wall. The reception level and entrance hall open out onto a terrace where lunch, tea, and cocktails are served, allowing guests prime views over the hilly city and Pacific Ocean. There are quiet corners for those seeking a solitary moment, including a library and a piano bar, which comes to life in the evenings with live music.

Casas del Bosque is an award-winning boutique winery just outside Casablanca where, besides tasting the vintages, you can also learn how to prune grapevines or even the basics of wine-making in one-day workshops. You can also tour the estate on bicycle, along with a picnic lunch. If you just want to walk through the vines, you’ll find everything at its prettiest in December and January. Tanino, the Casas del Bosque’s excellent restaurant, has a menu designed to showcase the wine.

In a city built on steep terrain, it is a wonderful thing to have the option to ride up and down the hillsides rather than walk. In 1883, Valparaíso’s first funicular (ascensor), the hydraulic Ascensor Concepción, made it unnecessary for locals to climb hundreds of stairs every day. Today, about 15 of these little vehicles, most using electric power, are in operation; passengers ride for a small fee. The most popular one—and the one with the best views—is the Funicular Cerro Artillería. The Ascensor Concepción Prat is the oldest.

On the central coast north of Valparaíso, the beach resort town of Concón is popular with Chileans for its boardwalk, great restaurants, and, most of all, the 52 protected acres of monumental sand dunes that cascade down from high bluffs all the way to the sea. In addition to hikers, the dunes draw sandboarders who climb to the top, wax their rented boards by rubbing them with candle stubs, and then slide or sled down the slopes to the sound of the sea lions barking in the waters below.

The Cerro Alegre/Cerro Concepción neighborhood is wonderful for walking, with many promenades and terrific views of the bay. The hilly area still conveys the culture of the European immigrants, mostly German and British, who settled here in the 19th century. Visitors are often surprised by the non-Spanish influences in Valparaíso; street names, businesses and popular restaurants in this barrio bear testament to the multiplicity of cultures in the seaport.

Easter Island is a strange, remote, and magical place. After a full day of wandering around this tiny island, we were fortunate enough to witness an absolutely breathtaking sunset over the Pacific. The “beach” here is made up of pitch black volcanic stone. I found it to be utterly fascinating.

What was supposed to be the first drawbridge in South America ended up as a monument to inefficiency and made laughingstocks of those involved when, just before construction finished, it was discovered that one of the bridge’s two spans had been installed upside down. The $42 million project was later featured in the Discovery Channel documentary “Horrors of Calculation” as an engineering mistake too expensive to fix. The bridge, which spans the Cau Cau River in the lovely city of Valdivia, is unusable except as a background for selfies and a caution to anyone whose mind wanders during calculus class.