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Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

Jutting out from the northern district of Mosman, just south of Taronga Zoo, Bradleys Head offers one of the best perspectives of the Sydney Opera House, the Sydney Harbour Bridge and Fort Denison, among other attractions. Whether you come for a picnic or New Year’s Eve, fishing or hiking—the popular Bradleys Head to Chowder Bay walk links up with the even more epic Manly to Split Bridge track—this is Sydney at its best. If the natural beauty isn’t enough, Bradleys Head is also a historic site where the mast of the HMAS Sydney, a relic from the Royal Australian Navy, is mounted proudly and an old military mess hall now serves as a cafe.

Vancouver’s serene waters serve as the perfect playground for kayakers and stand-up paddleboarders. Newbies can book two-hour “tasters” at Ecomarine’s Granville Island or Jericho Beach locations, while more adventurous paddlers—of any level—can jump right into tours, like the summer sunset excursion along the scenic shores of False Creek (a protected inlet) and English Bay (part of the Strait of Georgia). While most tours last a half or whole day, Ecomarine also offers more hard-core expeditions, like the weeklong trip to Haida Gwaii. This craggy, rain-forested archipelago is often referred to as Canada’s Galápagos for its vast number of endemic species. It also has a wealth of First Nations heritage sites just waiting to be explored.

The edges of the iceberg (technically, bergy bits) are a great place for animal sightings. Harbor seals ride the floes, basking in the sun; orca whales prowl just around the ice barrier, waiting for an unwary seal to come out to where the whales’ sonar can reach. Humpbacks feed off krill upwellings, and bald eagles are as common as sparrows. Those who are very lucky (and who have good spotting scopes) can see mountain goats on occasion. They’re a wonder in the wild: How does a goat get up 3,200 meters of rock?

No island getaway is complete without seeing gorgeous scenery you’d never, ever see at home—and Willemstad’s floating bridge delivers! Built in 1888, “Our Swinging Old Lady” is supported by 16 pontoon boats and two motors. When you hear the siren, look to see the entrance gates slam shut and moments later, the bridge sways to accommodate passing ships. (If you don’t feel like waiting for Queen Emma to reopen, you can take a ferry between Willemstad’s Punda and Otrobanda districts instead.) At night, the bridge’s lights cast a shimmering rainbow on the water.

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.

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.

The owners of this playful shop, Jo and Micko, are passionate about handcrafted, natural body care. That led to the launch of a range of sensory products in 1999. But their love for design and vintage fashion got the better of them, resulting in a limited-edition range of garments as well. In addition to the racks of timeless dresses and petticoats, visitors can buy fragrant perfumes, soy candles and soaps made from essential oils, clays, seeds, and no palm oil. Varieties range from coconut and spearmint to “pussy wash,” “ass wash,” and “cock wash"—for the cats, donkeys and roosters among us.

This restaurant in northwest Tasmania—defined by a blond wood wall, white bucket chairs, and stoneware dishes—wouldn’t feel out of place in hip Hobart, or even in Sydney or Melbourne. It’s Scandinavian in style, but the food veers more French and Italian: pork, chorizo, and pea risotto; seared scallops with pickled fennel; duck rillettes; a lemon brûlée tart with raspberry chantilly cream. But seven-course degustation dinners and acoustic-guitar sessions are very, well, Tasmanian. Degustation dishes could feature everything from mint-cured ocean trout and sous vide squid for starters to entrées of slow-cooked lamb belly and confit duck served over charred peach purée and prosciutto.

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.