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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.

Even fun has a shelf life. This is what runs through my mind as I walk around Spreepark, the abandoned, dilapidated amusement park in Berlin. When East Germany and the GDR fell, so did many of the businesses operating under the rules of communism. They were never really able to make the transition to capitalism successfully. Spreepark, located in the East German part of Berlin, was one such casualty. Even though Spreepark is “dead,” it is now a present-day photographic amusement park. The park is closely guarded, and trespassing is typical but also dangerous, so an enthusiastic, enterprising young man has started running tours on the weekend, providing access to shoot away to your heart’s content. The rides and stands have all deteriorated in place over the years, which makes for an eerie photographic landscape. More Information: Tour information (only in German) – www.berliner-spreepark.de/ – Tours are given mainly on the weekends. If you want to go on a tour, contact him, as he does know a little English and you can at least book yourself into a tour and get access for photography—even if you don’t understand the stories.

Standing out in San Francisco‘s Marina District, this historic landmark is a leftover from the 1915 Pan-Pacific International Expo and was designed by Bernard R. Maybeck, a student of the École des Beaux-Arts. His vision was to give the impression of ancient Roman ruins. When the fair concluded, the Palace of Fine Arts proved too beautiful to raze. Maybeck had intended the Palace to fall into ruins (in keeping with his original vision), and it did for years. It was used as a storage depot after World War II and as a warehouse for the Parks Department. In the late 1950s, a local city official led an effort to face-lift the building. The Palace of Fine Arts was rebuilt and is now enjoyed by visitors who walk beneath the towering colonnade and the grand rotunda.

Located in East End Village and painted in Anguillan flag colors, the Heritage Collection is Anguilla’s only museum. It showcases the island’s history and geology from the time of the Arawaks to the 1969 Anguillan revolution, with additional displays on the British invasion (derisively called the “Bay of Piglets” by the press) as well as on Queen Elizabeth II’s royal visit. Established in 1996, its collection includes photographs and artifacts from the island’s major eras, including the days of slavery and the phosphate trade. If you’re lucky you’ll meet Colville Petty, the museum curator and founder, and garner some of his unique insight on Anguillan history.

While rue Ste-Catherine is the home of Montréal’s international brands and shopping centers, avenue Laurier Ouest is the place to head if you are more interested in local designers and small boutiques. The street connects the neighborhoods of Outremont and trendy Mile End, both up the hill from Old Montréal. A number of restaurants here, and on nearby avenue Bernard, have alfresco sidewalk dining when the weather is warm.

Pairings are everything at Ram’s Gate, one of the first wineries on the drive to wine country from San Francisco. First is the combination of sights: the wonders of architect Howard Backen’s open-concept tasting room in a refurbished barn and the panoramic vistas of Carneros and San Pablo Bay. Next is the marriage of wine and food—winemaker Jeff Gaffner’s single-vineyard designate chardonnays and pinot noirs matched perfectly with seasonal small bites from executive chef Taylr Benham Cuneo. The most popular tasting is called “Palate Play,” which marries five wines with five dishes from the kitchen. For a truly unparalleled afternoon, book the three-hour Vineyard Table experience, an immersion for four to 10 people that includes a glass of bubbly, a guided tour of the winery and on-site gardens, and a custom-designed meal with wine pairings served at a table in the vineyard. There are other, less involved ways to experience Ram’s Gate: seated wine tastings, stand-alone site tours, and picnics down by the pond. Whatever your fancy, just be sure to make a reservation before you go.

Fish from tins, fish whose fins were in the sea just this morning—they’re all stars at Saltie Girl, a compact seafood bar and restaurant in the Back Bay from Kathy Sidell of MET restaurant fame. Whether you love your seafood raw, smoked, fried, or—yes—out of a can, settle into one of the 11 stools in front of the active kitchen to watch as your dinner is prepared or, well, opened. Of course, you’re not paying top dollar for Chicken of the Sea here: The tinned seafood comes from small artisan producers, sustainably sourced, packed fresh, and shipped from around the world. Caviar, squid, anchovies, cod liver, and cockles are among the savories served cold with dipping sauces and crusty bread.

The San Francisco Proper Hotel is the hottest new hotel in town. The reason why? International grande dame of maximalism, designer Kelly Wearstler, revamped a down-and-out tourist hotel deep in the heart of the city, and established the Proper as a magnet for trendsetting visitors and locals. When guests arrive at the 131-room hotel and step inside the flatiron building, they’re treated to Wearstler’s signature pattern-on-pattern aesthetic. In the ground floor lobby, Wearstler sets the mood with salon-style seating areas using richly reupholstered vintage furnishings and Cubism-inspired paintings. Michael Adams, formerly of Central Kitchen, oversees the hotel’s main restaurant, Villon. And while the Proper isn’t the place for those looking for a Zen retreat, it is the place to order a Fifi the Flea cocktail (Tequila Ocho Plata, Ancho Reyes, Ancho Reyes Verde, grapefruit, honey, vanilla, lime, smoked salt) at Charmaine’s, the stylish rooftop bar. Between the fire pits and the bird’s-eye view of Market Street all the way to the bay, it’s no wonder the Proper has become the destination to see and be seen.

Along with a great view of San Francisco, Treasure Island is home to a popular flea market, formerly Treasure Island Flea, and now called TreasureFest. Each month around 400 curated vendors set up and peddle their wares. Stalls offer antiques, originally designed art and clothing, and vintage curiosities. You will also find about two dozen food trucks, live music, kids’ games and activities, and some local wine sellers to fuel your shopping fire. The two-day flea market takes place the last weekend of every month. Launched in 2011 to support local artists and entrepreneurs, Treasure Island Flea is now a must-do Bay Area event.

There’s no better place than Vancouver to try a Vancouver cocktail, it’s the perfect pre-dinner sharpener, although it works rather well as an after-dinner treat too. It’s said to have been created at the Sylvia Hotel down on English Bay in the 1950s and its fans included Errol Flynn. It’s a riff on the Martinez, made of gin, Benedictine, sweet Vermouth and orange bitters. Although the Sylvia is, of course, the most authentic place to try it, I have to recommend you make for the all-weather patio at Cin Cin to sip bartender David Wolowidnyk’s version which is smooth, delicious, and really far too good to just have one...

If you grow tired of tasting your way around menus of typical Québecois dishes, Stash Café is an appealing alternative in Old Montréal. This budget-friendly Polish restaurant has the feel of an inviting tavern, with seating in old church pews. The menu consists of Polish favorites: perfectly prepared pierogis, kielbasa, and hearty borscht. If you are in Montréal on a gray winter day, it’s a menu that will warm you up before you bundle up again to continue your sightseeing.

Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.

Join throngs of locals on the five-minute ferry ride across Victoria Harbour between the Tsim Sha Tsui cruise pier in Kowloon, on the mainland side, and the Central Pier on Hong Kong Island (a slightly longer ride goes to Wan Chai on Hong Kong Island). This is not just any ferry: The historic green and white Star Ferries have been moving the masses back and forth for decades, with the origins of the company going back to 1880 with the service of a single steamboat, the Morning Star. Today, the classic wooden boats make the trip many times daily, and a ride provides a great view of the city’s famous skyline and a whiff of nostalgia to boot.

While Cape Point is not, in fact, the southernmost tip of Africa—as is often claimed—it is generally accepted that the Indian and Atlantic oceans meet somewhere between here and the real tip, Cape Agulhas. Still, Cape Point is about as dramatic as you can get, with the land falling steeply away on three sides, the wind whipping around the cliffs, and the ocean churning below. The road to the point, at the end of a drive from Cape Town, goes through 20 miles of nature reserve full of baboons and antelopes. For those who don’t want to walk up to the lighthouse, there is a funicular, but to reach the point itself, you’re going to have to hike.

Baseball had nothing to do with the naming of Fenway Park: The stadium gets its moniker from the nearby Back Bay Fens, a stretch of saltwater marsh in the heart of Boston that was landscaped into a park by Frederick Law Olmsted. The Fens are among the wilder parts of the Emerald Necklace, 1,100 acres of parklands running from the Charles River to Brookline that include familiar spaces like the Boston Common and Boston Public Garden but also less-traveled (by visitors, anyway) sections like Olmsted Park, Jamaica Pond, the Arnold Arboretum, and Franklin Park. The arboretum, part of Harvard University and established in 1872, is one of Olmsted’s most unaltered terrains, with paths running up and around 261 acres of woodland interspersed with a curated collection of trees, plants, shrubs, and vines native to New England.