Sip Across the Southern Cone. When the rest of the world is slipping into spring, retreat south to the fall to experience the magic of the annual grape harvest in the Southern Cone. On this trip, the ultimate food-and-wine triple-header, move from the misty morning valleys of Chile and soaring Andes Mountains to the sun-kissed wine country of Argentina, and into the verdant hillsides of coastal Uruguay. Begin in Chile where wines are diverse as the topography from coastal Pinot to Riesling and heady Cabernet inland (trust us, you’ll find out soon enough). Then, it’s eastward to Mendoza, land of Malbec, where you may savor the best steak in this lifetime. In Uruguay, be indoctrinated in the school of Tannat, their hearty local red. Between the succulent feasts and almost daily wine tastings, experience some of South America’s finest landscapes through Alamo-studded lanes, snow-capped mountains, gauchos tending their cattle. But it’s the people—those winemakers and artisans who will be long lost family by the time you say tchau. Your palate wants to go already.

Day 1
Arrive in Santiago, Chile’s modern, cosmopolitan capital at the feet of the towering Andes. Check into your hotel situated in the charming Lastarria neighborhood near the central park and museum area. A handsome, “recycled” mansion, settle into your suite. The morning is yours to freshen up, relax, or explore.

At noon, meet with the group and your host, to explore the labyrinth of stands at Santiago’s sprawling wholesale market dating back to the late 1800s. A picturesque mishmash of stalls, vendors hawk the freshest seasonal fruits and vegetables, local cheeses, a plethora of meats, mounds of spices, and indigenous foodstuffs. Wander through the maze of picadas, joints, and pull up a stool at an old school eatery focused on Chilean classics like sweet corn tamales, steaming brothy stews, and avocado-laden sandwiches. Cross the Mapocho River to the bustling fish market to visit our favorite mongers and understand the importance of the Humboldt current in Chilean seafood. Break at our favorite joint, serving traditional seafood dishes with frothy Pisco Sours. Afterwards, return to the hotel in the mid-afternoon for a well-deserved nap.

Tonight, meet at Liz Caskey´s spacious private apartment overlooking Santiago’s Parque Forestal with panoramic views of the Fine Arts Museum and San Cristóbal hill. Sip some of our favorite boutique wines and nosh on homemade tapas drawing their inspiration from Chilean recipes and the primo ingredients. Welcome again to Chile! (Lastarria Boutique Hotel)

Day 2
Head northwest of the capital to the Casablanca wine valley where white whites and Pinot Noir have thrived with delicious natural acidity, potent fruit, mineral, and earthy aromas. Head to a tiny boutique winery experimenting with Malbec, Cabernet Franc, and Syrah with tremendous results. First, saddle up on horseback for a short ride into surrounding eucaliptus forest and vineyards. Aftewards, sit down to a selection of their premium wines with the resident sommelier.

Visit a family-owned winery tucked in a cool corner on the eucalyptus-peppered hillsides. They excel at making limited amounts of lip-smacking Sauvignon Blanc, satiny Pinot Noir, and electric Northern Rhone-style Syrah. Visit the petit winery with the winemaker, or sommelier, and then sit down to a tasting of their premium line with a sweeping view of the vines, valley, and surrounding hills.

Snake down a winding mountain road through a pine forest. The hairpin turns slowly reveal the cliffs and turquoise waters of Chile’s rugged coastline below. At road’s end, a colorful jumble of clapboard houses clings to the rocks overlooking the wild Pacific. Here, artisan fishing is a way of life. Every morning, fishermen head out to sea in dinghies in search of rockfish, grouper, and shellfish. Lunch is across the sand and past the fishing boats at a simple restaurant overlooking the sea. Run by an extraordinary woman and her two sons, the house specialty is fresh seafood that never hits ice. Savor some of the most classic seafood dishes in Chile prepared in traditional dishes in greda, clay pots, like: pil pil (seafood in a chili-garlic sauce) or machas a la parmesana (razor clams with Parmesan.) Also try the fresh abalones, seared grouper, paired with a flight of our favorite coastal wines. Return to Santiago in the afternoon. (Lastarria Boutique Hotel)

Day 3
Travel south from Santiago into the tranquil countryside with patchwork fields, red-tiled roofs, and the jagged peaks of the Andes. The destination is the Colchagua wine valley, renowned for its “big” red wines such as Cabernet Sauvignon, Syrah, and Chile’s flagship Carmenere.

Drive to the western reaches of the valley to visit a top rated garage winery. Here, the perfect combination of granite soil and climatic convene to produce show-stopping Syrah and Malbec. Understand the unique viticulture with the winemaker and sit down to a special tasting from their mirador overlooking the valley.

Continue to a horseshoe-shaped micro valley, renowned for its outstanding reds. Visit a stunning winery, belonging to the Gran Marnier family, perhaps Chile’s most chic, innovative, and highly acclaimed. Named 2008 Wine of the Year by Wine Spectator, the winery’s opulent setting is buried deep in the hillside. Marvel at the state-of-the-art facilities before an exclusive tasting in their unique second-year barrel cellar. After your tasting, enjoy a fantastic lunch amid the vineyards.

Visit one of Colchagua’s top boutique wineries producing one single Cabernet-Carmenere blend from 115 year-old rootstock. Walk amid the craggy vines and admire the restored colonial cellar. Appreciate the exquisite 2008 harvest, known for remarkable finesse and balance.

Head to the country town of Santa Cruz. Check into your comfortable colonial-style hotel on the main square adorned with wrought-iron balconies and fuchsia bougainvillea. In the evening, meet a friend in their private home who makes traditional artisan liquors utilizing a centuries-old recipes, organic native herbs, fruits and dried spices. Savor a delicious aperitif before dinner on your own. (Hotel Santa Cruz Plaza)

Day 4
After checkout, drive north to foothills of the Cachapoal Valley. Visit a project conceived with the sole objective of making a grand cru wine from Chile. No detail has been spared here—and the result is concentrated wines with great structure, soft tannins, bright aromas, and a tremendous balance. Get to know the soul of this wine with a tasting of the outstanding 2007 vintage. Afterwards, stay on for a light lunch with sweeping views of the valley below.

Watch the scenery change from tranquil countryside to bustling city as you head back to Santiago. Take a short, scenic flight over the Andes to Mendoza, Argentina’s famed wine country. Arrive in a tucked-away corner of western Argentina. Mendoza sits nestled beneath towering snow-capped Andean peaks, one of the world’s striking wine regions. This desert oasis gives birth to world-class Malbec, Syrah and Cabernet, along with a free-spirited, laid back lifestyle.

Make a beeline for a blissful retreat for wine lovers outside the city. Arrive at the newest luxury hotel in Mendoza with low-slung modernist structure in raw concrete surrounded by lovely grounds and vines. Check into your room with modern, sleek décor and an attractive contrast of concrete and hardwood, patterned textiles and art. Unwind with the house wine and patio area to soak up the glorious Mendoza sunshine.

In the evening, head to Argentina’s celebrity chef’s flagship restaurant, located inside an elegant century-old bodega. Admire the handsome architecture with its huge antique iron windows overlooking the terrace and garden. Dive into the simple, and delicious, food philosophy using only the finest Argentine meats and fresh local produce. Try the signature burnt carrot salad, chivito (baby goat), or salt-crusted chicken, all slow roasted in the traditional outdoor mud oven. (Entre Cielos)

Day 5
After breakfast, become acquainted with Luján de Cuyo, the self-proclaimed Tierra del Malbec, Land of Malbec. Explore the different microclimates of the area to develop an appreciation of why the desert-like climate and high altitude provide the ideal place for the grape to express itself.

Visit a small bodega on the banks of the stony Mendoza River. Producing small quantities of single vineyards and elegant blends, this winery is an international reference for its showstopping Malbec. Understand their non-interventionist winemaking philosophy and taste different barrel samples of their Malbec.

Arrive at a winery hidden off a dusty country road. Chime the bell of this tiny garage winery, whose owner and winemaker is considered to be one of the fathers of Mendocino terroir. Using their own savings, ingenuity, and passion, his family makes truly handcrafted wines and artisan olive oil. This is as local as it gets!

Stop at state-of-the-art winery, surrounded by some of Mendoza’s oldest vineyards. Savor a five-course gourmet lunch ingeniously paired with their full line of Malbecs, from rosé to. Delight in Andean views elegant setting, and superior service.

Visit friends dedicated to making the very best wines possible: long, satiny and ripe wines for the soul. Visit their petite family winery and receive a warm welcome that makes you feel like… family! Learn the art of their craft, taste straight from the barrels, and understand how they slowly built their bodega through hard work and heartfelt passion. Sit down for a relaxed tasting of their wines and cheeses.

This evening, enjoy a detox in the traditional-style Turkish hammam circuit and spa. Sweat, detox, and let the masseuses nimble fingers knead away any stress. Dinner is on your own. (Entre Cielos)

Day 6
This morning, visit an estate on the sloping plateau of Alto Agrelo whose focus is on producing limited edition wines. Be received by their warm team to understand their concept of viticulture; visit the sleek, pristine winery with concrete construction; and then delight in an educational tasting of their fabulous, well-balanced icon wines.

Drive over the scenic, rolling hills an hour south of Mendoza to the high-altitude Uco Valley. Here, surrounded by the grandeur of the Andes Mountains, many wineries are experimenting with new varietals such as Cabernet, Tempranillo, and Syrah. A lush agricultural valley in the midst of a parched desert, the valley floor is dotted with almond trees and fruit orchards.

Journey to a family-owned boutique winery with some of Uco’s most coveted terroir. The objective here is on quality not quantity, and, of course, expressing Uco’s stony, high-altitude soil in the full, generous wines. Be welcomed into their guesthouse for a wonderful tasting with local cheeses to accompany the wines. Stay on for a private lunch where each course is paired with their wonderful house wines. Enjoy the views of the Andes from their balmy terrace. Ahh, such is the life in Mendoza!

After lunch, visit the newest winery an extraordinary French winemaker’s “wine condo”. As the Mendoza plateau rises into the Andes, this bodega is an amazing intersection of architectural innovation combined with classic winemaking methods. The owners are proprietors of two chateaux in Bordeaux and their wines reflect the intensity of the sun– rich, complex, and elegantly crafted. Visit the facilities and sit down to an exclusive tasting. (Entre Cielos)

Day 7
Enjoy your last breakfast in Mendoza. Transfer to the Mendoza airport for your flight to Aeroparque (Buenos Aires) and connection to Montevideo, Uruguay. Arrive in Montevideo and drive into the Uruguayan capital along the rambla, the coastal road that connects the Uruguayan capital along the sandy shores of the Río de la Plata.

Check into your all-suites hotel, where each floor is completely dedicated to wine. Rooms are comfortable, contemporary, and simple with separate kitchen space and wine glasses. Set in the shady residential neighborhood of Pocitos, its ideal location is close to the beach, shopping, cafés, and top restaurants. Tonight, take a break from meat. With hundreds of miles of coastline, dive into a plethora of local seafood at one of Montevideo’s top restaurants in the upscale neighborhood of Punta Carretas. Try some of Uruguay’s lesser known varietals like Sauvignon Gris with the local chiparrones (seared baby squid), abadejo (local white fish), and mussels from José Ignacio. (My Suites Montevideo)

Day 8
Get ready for an education in Uruguay’s undiscovered wines. Here, the Atlantic climate and mineral-rich soils is unique from wine-producing cousins Chile & Argentina—and so is the expression. Perhaps the wines are slightly Old World in style: elegant, less alcohol, in some cases, very tannic. Such is the case of the signature grape, Tannat, yielding full body wines with intense color, gripping tannins, and a lovely austerity that grows on you.

Visit small artisan winery making handcrafted Tannat in micro batches. Everything here is a family effort, enthused with their passion of sharing the land and its traditions. Meet the family, learn about their vision, and taste their outstanding line of Tannat and blends.
Drive to Uruguay’s “largest” wineries. Still a hands-on family operation, this family has blazed the trail for Uruguay’s wines to leave on the external market. Visit the vineyards, the century-old cellar, followed by a private tasting of their premium wines.

End the day with a visit to a boutique winery that’s been making premium wines for over 70 years. The secret to their success? Attention to detail, a love for their land and grapes. Meet the family to understand their unique wine vision by walking the vineyards. Then, be invited into the old casona, family home, for a private Uruguayan-style barbeque with grilled meats and crunchy fresh salads paired with a tasting of the best house wines. Local, authentic, inspiring. (My Suites Montevideo)

Day 9
This morning after checkout, head north just outside Montevideo to Canelón Chico with soft, rolling hills and lush vegetation. Stop by a small boutique winery going three generations strong. Let the owner/winemaker take you out into the estate to understand better the nuances of wine growing in Uruguay. Back at the bodega, sit down to a tasting of his excellent Brut (a tradition in Uruguayan wineries), and selection of his top Tannat and blends.

After, drop in on the country’s newest boutique project. The dream of a wine aficionado, here the philosophy is “less is more”: less intervention, less quantity, and maximum quality. Beyond Tannat, they work with Merlot, Tannat, Tempranillo, Albariño and Chardonnay. Sit down to an elegant yet casual lunch featuring dishes like estate lamb, grilled fish, beef, and garden vegetables with a flight of their top wines.

Transfer to the airport for your departing flight and connections. Adiós!