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I don’t know whether it was the early morning fog, the rolling hills surrounding the vineyard, or the grapes themselves that made me do a double-take: Was I really in Chile’s Colchagua Valley, or was I back in California’s Sonoma Valley? With its intoxicating location and old world charm, Casa Silva (the colonial-style inn that sits in the midst of the family vineyard) has the best of both. It’s a place to relax, tour the surrounding vineyards, and – naturally -- drink their own varietals (especially the Sauvignon Gris, Sauvignon Blanc, and Petit Verdot). With only seven rooms, Casa Silva sits somewhere between a B&B and a guest house, with shabby chic rooms that are a throwback to Chile’s colonial era. We snagged room no. 4, with high ceilings and a comfy four-poster bed as well as an oversized bathroom. While the inn itself is special, the restaurant is worth a visit on its own. It has a clubhouse feel, overlooking the family polo field, but with unique and breathtaking views of the Andes. Hotel guests can take a leisurely 20-minute walk through the vineyard to the restaurant, which features Chilean specialties like conger eel, queso fresco, and tuna ceviche in one of the most dramatic settings I’ve ever enjoyed. (And don’t pass up the mote con huesillos, aka “wheat berry peach dessert.”) Finally, not to be missed: the tour of Vina Casa Silva, which houses one of Chile’s most up-to-date wine facilities and the family’s collection of perfectly restored antique cars.

Perched high above the Bay of Positano, Il San Pietro is the epitome of Italian seaside glamour—the hotel has attracted a coterie of international VIPs since its opening in 1970, including Gregory Peck, George Clooney, and Julia Roberts—but retains the charm of a family-run inn. Michelin-starred Zass restaurant culls ingredients from the property’s organic gardens, which spill down to the sea across 10 terraces teeming with local produce, and rooms feature custom ceramic tiles made in local factories using traditional techniques. If the 400 steps down to Positano’s only private beach sound daunting, an elevator cuts through the rock to water level, where tangerine loungers on the stone sundeck give way to a cove with sandy shores. Here, breezy Carlino restaurant serves up lemon spaghetti beneath a cheerful thatched roof. Prefer more active endeavors? Hugging the cliff face above, seaside tennis courts serve up sets with a dazzling view.

Original Joe’s has the same birth year as another pretty famous San Francisco landmark: the Golden Gate Bridge. Both are definitely worth checking out, but only Original Joe’s will serve you a hearty Italian meal in a red leather booth. Back in 1937, the restaurant was a 14-stool counter on Taylor Street where immigrant and family patriarch Tony Rodin served Croatian-Italian-American comfort food. Original Joe’s is run by the third generation of the family. A fire destroyed the first location in 2007, but the corner spot in North Beach that opened five years later can’t be beat. Inside, the family’s San Francisco history is revealed by walls hung with black-and-white photos, letters, and other ephemera. The menu showcases some of Tony’s recipes, such as eggplant parmigiana, Joe’s meatballs, and veal parmigiana. Those counter stools are there, too, saved from the fire and brought over to the new Original Joe’s.

Singapore may not have bicycle lanes on its roads, but the country does have a wonderful and growing network of bike-friendly asphalt paths along its many canals and rivers that are sometimes joined up with pathways in parks and along old rail corridors (in Singapore, they’re called park connectors). An easy 3-mile round-trip stretch to sample runs along the Singapore River. Join the riverside pathway just off Zion Road near the Great World City shopping mall—you can rent your chariot nearby from Bike Connect, at 23 Hoot Kiam Road—or grab a two-wheeler from the now ubiquitous bike-share steeds parked everywhere. Pedal all the way to the old shophouses of Boat Quay where the river empties into Marina Bay and then the South China Sea at the heart of Singapore’s colonial core. From there, get a glimpse of the grand Fullerton Hotel (once the national post office), the Asian Civilisations Museum (originally intended to be the city’s courthouse), and several historic bridges.

Renowned Costa Rican architect Ronald Zürcher looked to his country’s colonial past when designing this hacienda-style property—witness its central courtyard, arched doorways, and terra-cotta roofs. Set amid a 30-acre coffee plantation just outside the capital city of San Jose, the hotel’s 308 traditional accommodations follow suit with dark wood furnishings, but a modern aesthetic pervades renovated guest rooms with streamlined furniture, intricately patterned bathroom tiles, and expansive views that extend from green lawns to forested mountains and urban skyline; some include small balconies that overlook the hotel’s two pools. On-site dining options include gourmet takes on Costa Rican fare at Hacienda Kitchen, Peruvian specialties at La Isabela, and fresh-made sushi at La Castilla, as well as a sports bar and café. The open-air great room invites reading and quiet conversations, but if you’re up for something a little more energetic, there are tennis courts, a driving range, a fitness center, and invigorating coffee scrubs at the spa.

On the non-descript, busy corner of Bucareli and Morelos streets in Mexico City is a café with a famous history: Fidel Castro and Che Guevarra met here at Café La Habana several times, chain smoking and drinking strong coffee, to plan the Cuban Revolution. Nowadays, you can still get excellent coffee—and pretty good food—while you plan something a little less dramatic (but more enjoyable), like your vacation itinerary. Old journalists and businessmen congregate here for hours on end while salt-of-the-earth, slightly surly waitresses take your order and bring you your food and drink. Come for breakfast and order their chilaquiles, motuleños, or molletes, and wash it down with an espresso or café americano.

Founded in 1971 as the first women-owned and operated community center in the country, the San Francisco Women’s Centers has been working to guarantee a safe space and reliable social services for women and girls in the city. And since 1979, they’ve done it from the Women’s Building—or El Edificio de Mujeres—in the Mission, a women-led community space advocating self-determination, gender equality and social justice. Through education, cultural arts activities, and economic services (all available in both English and Spanish), the Women’s Building helps more than 20,000 low-income women and their families every year. Looking to take part? Visit the website to see their list of events, rental spaces and equipment, and volunteer opportunities.

From its new location on the Singel, Supperclub maintains the old traditions of one of Amsterdam’s most innovative nightclubs. In few other upscale restaurants can you take off your shoes, get in an oversize bed with friends, and savor an unconventional five-course meal over the course of an evening. But supperclub is not for everyone. Part culinary journey, burlesque/vaudeville club, cocktail bar and experimental free state, it’s a unique if somewhat pricey venue for a fun, quirky evening with friends or business colleagues. When not wintering in India, flamboyant Howie may greet you, ushering your posse to La Salon Neige, where you’ll scoop courses from hospital bowls, ash trays and sensual models dressed in slices of Carpaccio, brandishing salad dressing in syringes and deep-fried cricket tidbits—crunchy croutons! Opt for the upper level lounge and you can watch from above as dykes, belly dancers and aerial artists perform. Don’t worry about crumbs in bed; get into the act while the drag queens vamp and the dancers swirl. Between courses, enjoy a Lavender Love or Leap of Faith cocktail in the Chapter 21 bar. Or venture to the downstairs smoking room that doubles as a gay toilet. While puffing on a joint, don’t be surprised if spontaneous music erupts or locals engage you in conversation. There are supperclubs in Istanbul, London, Los Angeles and San Francisco, but this is the original. And there’s nothing conventional about it!

A 1,200-acre green space filled with museums, theaters, and gardens, Balboa Park is the center of art and culture in San Diego. It’s also one of the city’s most historic sites, built for the Panama–California exhibition in 1915. While the museums are definitely worth seeing, there are also a number of free attractions, including the photogenic Botanical Building, which houses more than 2,100 plants (including Venus flytraps); the Desert Garden, filled with succulents from around the world; and a sculpture court with works by Miró and Rodin. For one of the area’s best views, purchase a timed ticket to climb the California Tower in the Museum of Man. The ornate structure reopened to the public in 2015 after being closed for nearly 80 years and features a spiral staircase to the eighth floor, where you can catch a glimpse of the Cuyamaca Mountains, the Cabrillo Bridge, and even Mexico’s Coronado Islands.

Once a separate municipality, San Ángel—in the city’s south, nestled into its western foothills—is a leafy, genteel enclave whose relative isolation adds a soigné feel (for better or worse) you won’t find in neighboring Coyoacán. Ground zero for promenading is quaint Plaza San Jacinto, whose cute parish church (and beautiful cloister garden) is a sort of spiritual last stand amid the surrounding area’s high-toned consumerism. That said, the plaza’s true spirit comes alive Saturdays, at the so-called Bazar Sábado, an artisanal market that fills the area with stall after stall of handmade jewelry, textiles, crafts, and accessories, plus a great deal of art—some finer, some less so—in styles that go from hippie to haute. Strolling musicians and performers add to the carnival atmosphere.

Montage is a hip, and highly curated collection of vintage men’s and women’s clothing, jewelry, and accessories, focused on the 1940’s through the 1990’s. The jewelry is particularly worthy of note, as much of their collection is made from broken or scrap pieces that have been reinvented and revitalized.

Thanks to an owner and several staff members who hail from Italy, this Neapolitan-style pizzeria has an authentic feel that locals love. Its popularity shows—San Diego restaurants are rarely crowded, yet Buona Forchetta often boasts wait times of up to two hours. Much of the dining happens outside beneath an awning. Indoors, simple decor lets the gold Stefano Ferrara pizza oven shine. Go for perfectly blistered pies like the Nicola (mozzarella, mushroom, prosciutto di Parma, and truffle oil) or the Isabella (buffalo mozzarella, sun-dried tomatoes, onions, goat cheese, and rosemary). If Point Loma is more convenient, know that there’s a second, larger location called Officine Buona Forchetta in Liberty Station.

On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

In 1946, Picasso worked from a studio in the Château Grimaldi of Antibes, creating 23 paintings and 44 illustrations that he gifted to the town. Later, 78 pieces that he designed for the Madoura pottery studios in Vallauris were added to the collection and the château became the world’s first Picasso museum. The nearby Archaeology Museum is housed in a historic fort and explores Antibes’s origin as the ancient Greek town Antipolis.

La Gintonería, in the less-traversed neighborhood of Gros, could very well be the best gin-tonic in San Sebastián. With two shelves laden with premium and hard-to-find gins, it’s a gintonaholic’s dream. They have a selection of premium tonics and an arsenal of techniques to match. Watch as they instantaneously infuse your gin with cardamom using a pellet of dry ice. Or inhale as they drip just a few drops of bitters into your fishbowl glass. Whatever gin you choose, you are in for one of the best mixed drinks of your life.