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With the temperature sitting pretty around 75 degrees at all times, walking around Medellín is pure pleasure. To get a deeper understanding of the history of and life in Colombia, don’t miss the Museo Casa de la Memoria, which recounts Colombia’s brutal civil war. After, head to the Parque de los Pies Descalzos, where you get to kick off your shoes and, like all the other kids and adults, run through fountains. For a stellar view, hop a Metrocable car to the neighborhood of Santo Domingo.

From folk art to cowboy boots, San Antonio’s rich history and geography continues to inspire local artisans. There are shopping destinations both enclosed and open air all around the city to please every taste, from the Shops at La Cantera to Blue Star Contemporary Arts and a nearby flea market that features a giant sign shaped like armadillo. Save Sunday mornings for brunch and shopping along the River Walk.

As the name suggests, you can shout your order from the sidewalk and by the time you get to the counter, they’ve already served up your empanadas. Try the time-tested caldo mayo, a house-specialty beef broth that’s a perfect hangover remedy, especially with spicy salsa de ají, or hot pepper salsa, on top. Members of the Chilean judiciary are often seen here having a tintito, a dainty glass of red wine, before beginning the day’s proceedings. El Rapido opened in the thirties and has been operating ever since—don’t miss this quaint and tasty bit of history.

Genuine Magallanes fare such as open-flame, spit-roasted lamb is what you find on the menu at this bucolic oceanside estate on the Eberhard Fjord in Patagonia. Aperitifs in hand, visitors can watch how the flavor-packed food that just keeps coming is prepared, and the service is a paean to Patagonia’s renowned hospitality. Connoisseurs recommend ordering the matambre, an especially tasty cut of beef. Tables hold parties of six or more, and individual diners are seated with whatever group can accommodate them. Reserve on the restaurant’s website (and remember that mobile service can be intermittent in this corner of the planet). Open mid-September to late April.

In Japan’s capital, youth dress up—and let loose—in over-the-top themed establishments.

Every day 2,000 empanadas are freshly made at this historic food landmark on the corner of Bandera and Huérfanos in El Centro. Santiaguinos pop in for a gooey fried cheese empanada slathered in hot chili sauce, piping hot. Stand in at the counter and order a “Pap” soda, flavored with Chilean papaya like the locals. Bandera 347, almost corner Huérfanos Phone: 56(2) 2672 2375

There’s much to see in Cusco and the surrounding area, but you can do a lot if you have three days to explore. Day 1: Visit the Incan ruins at Qorikancha in the morning. After lunch, wander the the Mercado San Pedro, then hike up to Sacsayhuaman for the sunset. Day 2: Take a colectivo to the Sacred Valley, Pisac and Ollantaytambo. Visit the ruins at Moray and the salt mines at Maras. Day 3: Watch Andean life go by at Plaza de Armas, then explore the galleries of Las Blas, the arts district.

Luxurious stays in rooms designed by Missoni, Bulgari, Lacroix, Versace, De La Renta, and more.

Chileans love “completos,” hot dogs with the works. Hogs took this concept and made it gourmet. Think hot dogs made with venison, lamb, pure frank, even rabbit. Then top it with items like caramelized onions, blue cheese, avocado, barbeque sauce, etc. The place is casual and standing room only to eat. Los Leones 40 (almost with Av. Providencia), Providencia (new location opening in Barrio Lastarria pronto!) Phone: 2235-4593

Pueblito Los Dominicos, an artisan village in eastern Santiago, is named after the church bearing the same name. This quaint center offers many quality handicrafts, from leather goods to lapis jewelry, Mapuche silver, and textiles. The setting is picturesque and if the hunger overcomes you, there are tasty empanadas de pino (beef empanadas) to hold you until dinner. Apoquindo 9085, Las Condes (Metro Los Dominicos)

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.

There are few more picturesque destinations than southern Italy’s Sorrentine peninsula. Stretching from the Bay of Naples to the Gulf of Salerno, the dramatic coastline is dotted with cliff-side towns that overlook brilliant blue waters and are favored by the jetset for their pebbled beaches and terraced gardens, dreamy lemon groves and villa retreats—think Amalfi, Ravello, Positano. Want your own piece of la dolce vita? Here are the hotels and resorts where you’ll find it.

Chilean wine is having a moment, with vintners discovering the myriad terroirs in the country spanning over 10 latitudes from the Pacific to the Andes--with over two dozen grape varietals. Many of the most avant-garde projects are small producers making garage or even underground wines alongside the reference wines. Enter Santiago Wine Club. The owners, two wine-loving friends (one French, one Chilean), teamed up to bring these inspiring wines to their loyal patrons in Barrio Lastarria. Arranged by valley, their are obscure, fun, serious wines for everyone. Owners are usually at the store and know their wines well. Perfect for any wine lover or drinker to take a bottle home--or drink while in town. Rosal 386, almost corner Victoria Subercaseux, Barrio Lastarria Phone: 56 (2) 2632 6596

Chilean society is quite conservative by many standards with the younger generations finally starting to cut loose. Get more playful. Be expressive. US expat Jayne Morgan saw the opportunity to fill the niche for erotic toys in the capital, starting as private bachelorette parties. The idea was a runaway success and she’s expanded to now have two stories in Providencia and Barrio Lastarria to satisfy the demand. Sex toys, games, outfits, and erotic books, all imported of high quality and good taste, are all laid in her attractive stories with attentive staff. Monjitas 580, 2nd Floor (in Bar The Clinic Building) Phone: 56 (2) 2632 5988

This little village fuels many a Chilean’s vision of the south—Germanic towns nestled among sapphire-hued lakes—and is often synonymous with summer vacation. Frutillar, just north of Puerto Varas, seems to be straight from Bavaria with its majestic “casonas,” built in the German tradition—a nod to the strong ancestry and settlement in the region. Frutillar’s lakefront has black-sand beaches, the shimmering lake dotted with white swans, magnificent views of the Osorno volcano, manicured lawns, and darling boutiques and cafes along the town’s streets. During the last week of January and first week of February, music lovers flock to Frutillar for the classical music festival where maestros from all over the world play in the Teatro del Lago, with some of the best acoustics in Chile. Besides strolling the relaxed lakefront, Frutillar is perfect to stop for a coffee and “kuchen,” a delectable German cake found throughout the lake district made with seasonal fruit.