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In the country’s wine region, you can pick grapes, sing songs, and keep ancient harvest traditions alive. It’s so much fun, you can taste it.

From some of America’s friendliest happy hours to outdoor patios with margaritas and live music aplenty, Alamo City is a top notch place to drink. San Antonio’s breweries are legend and one, Pearl Brewery, has been around so long that it has morphed into a destination all its own. Stop into the Hotel Emma on the River Walk for one of the city’s best cocktail menus.

After a string of personal losses, a writer heads to Tamil Nadu seeking solace from her sorrows. It takes two temples, a palm leaf astrologer, and the driver of a velour-lined taxi to make her feel whole again.

Chill out from the sun at the Blue Hole Mineral Spring, a 50-foot deep turquoise natural pool sitting 20 feet below a cave opening. Jump off the cliff edge like the Jamaican divers on site, if you’re feeling brave. Otherwise, head down slowly on the ladder and let go from a closer distance (like I did). There’s a small entrance fee to this park--located about a half-hour drive south of Negril in the town of Brighton--which includes access to an on site bar and restaurant, as well as an outdoor traditional swimming pool. But my guess is you’ll be too tempted by the underground shimmering and therapeutic fresh water.

Opened in 1950, the Jamaica Inn is one of the oldest and most gracefully aged of the classic Jamaica luxury resorts. It sits on its own private beach, which is rare in Jamaica, and each of the 52 suites and cottages has a Caribbean view. It is a timeless place, which may be why there are no TVs, radios, or clocks in the rooms, with a quiet serenity about it that may have been the appeal to such guests as Marilyn Monroe, Ian Fleming, and Katharine Hepburn. The grounds are immaculately kept, and the dining is as romantic as starlight and live music can make it. But the standout feature is that each suite has an oversize covered veranda that guests could literally live on. On it, they’ll find a full-size sofa, wingchair, breakfast table, coffee table, and, should one want to write home about it, writing desk.

Santa Fe is known for its distinct cuisine, unique architecture and strong art scene. Many hotels incorporate Southwestern elements into their architecture and design, such as adobe, kiva-style fireplaces, Native American artwork, and textiles.

Make the most of three days in Lima, South America’s second-largest city, and the third-largest desert city in the world. Day 1: Immerse yourself in pre-Columbian Peru at the Larco Museum, followed by a visit to the ruins of Huaca Pucllan, then taste the best ceviche and Pisco sours in the world in the Miraflores District. Day 2: Head to the Plaza de Armas in the historic center of the city, then to the lively, trendy Barranco District known for its art galleries, boutiques, and clubs. Day 3: Stroll through Parque del Amour overlooking the Pacific Ocean before heading to nearby Larcomar for some last-minute shopping.

In the city’s once-gritty fishermen’s quarter, a group of activist chefs is reviving—and reinventing—traditional cuisine.

Although you can find most cuisines in Berlin now, Jamaican food is nowhere near as ubiquitous as it is in, say, London, and it’s mostly relegated to shacks or pop-up stalls at festivals. Enter RosaCaleta, a full-service restaurant run by two transplants from Jamaica via New York who have created a perfect balance of traditional Jamaican dishes playfully reinvented for a European palate. White walls and a wood floor set the stage for a menu that includes oven-roasted pork fillet, fiery jerk guava chicken served with fluffy dumplings, and vegetarian dishes such as vegetable stews and lentil salads mixed with mango and ginger. The restaurant also has a superlative rum collection, used for an inspired cocktail list that is as fruit-filled as it is potent.

New York City’s history is rich and varied—from the glitter of the Gilded Age to the struggles of the immigrants who sought a better life in America, the city’s past shapes its present. There are still many opportunities to experience a different era here, before skyscrapers, smart phones and consumer culture took over. Take a quiet moment and step back in time.....

More than any other of the luxury beach-colonies that opened in Jamaica in the 1950s, Tryall has retained the feel of a private club. Yet this 2,200-acre property, with 87 villas, almost all having views that sweep down to the Caribbean, is Jamaica’s largest all-villa resort, and home to one of the Caribbean’s finest golf courses. Created by a group of Texas investors that included a future governor (John Connally) and future senator (Lloyd Bentsen), the resort, backing its own private beach just west of Montego Bay, continues to add villas notable for their luxury and individuality, one with a gallery devoted to Jamaican art, another with its own basketball court. Each villa has a dedicated staff, including a chef, housekeeper, butler, laundress, and gardener. And although each villa is essentially self-contained, the resort’s restored 1834 Georgian Great House, with its restaurant and bar, where events such as the manager’s cocktail party are held, serves as focal point for guests who want to “get out” without leaving the property.

From the North Fork and the Hamptons to the Catskills and beyond, New York offers several places to escape the city. Whether you want a luxurious hotel on the beach or a laidback retreat in the mountains, there’s a spot for every type of weekender. (Need more fodder for planning a weekend getaway from Gotham? We’ve got plenty.)

Aqua Nature Park, a well-maintained and verdant retreat 40 miles east of Negril, offers visitors a chance to take a dip and cool off in the Venture River. The river, which flows through a swimming hole on the property, has small, colorful fish and a cascade. Owner Steven delights in conducting walking tours of his family’s property, and can teach you quite a bit about the Jamaican plants and fruits he grows. (Don’t miss seeing the enormous cotton tree.) A casual restaurant and bar, with some reggae playing in the background, rounds this experience out into a lovely, low-key afternoon escape for couples, families, or anyone looking for a taste of real Jamaica.

AFAR chose a destination at random—by literally spinning a globe—and sent David Farley on a spontaneous journey to Bolivia.

When in Kingston, make time for a stop at Devon House, a grand 1891 Georgian mansion that was built for George Stiebel, Jamaica‘s first non-white millionaire. The lovely upright house and its 11 surrounding acres are now protected as a National Heritage Site, but that doesn’t mean that there’s not fun to be had. The sprawling grounds include shops, restaurants, a bakery, and a popular ice-cream shop, I-Scream. House tours can be arranged, but the grounds, landscaped with stately palms and fountains, are the highlight—it’s a great spot to take a stroll, read, shop, or dine. The mansion and its manicured lawns are also used for weddings and lavish events.