Sample Chile's art, cuisine, and culture on this luxury weeklong tour. You'll taste fine wines on vineyard tours in the lush Casablanca Valley and learn to make classic Chilean dishes, from ceviche to empanadas, in a cooking class with a local chef. Discover world-famous street art in UNESCO-listed Valparaíso and head to the rural Cajón de Maipo region for hikes to traditional villages. End in the vibrant capital, Santiago, for a walking tour of its historic landmarks.


  • Sample famous Chilean wines on a Casablanca Valley vineyard tour 
  • Take a street art tour in the UNESCO-listed coastal city of Valparaíso
  • Create classic Chilean dishes and pisco sours in a cooking class 
  • Visit Cajón de Maipo for rural hikes and traditional villages 
  • Explore Santiago's historic markets, plazas, and hilltop viewpoints

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Santiago, Transfer to Matetic Vineyards Casablanca Valley
Day 2 Casablanca Valley Wine Tour Casablanca Valley
Day 3 Transfer to Valparaíso, Cultural Tour of Viña del Mar & Valparaíso Valparaíso
Day 4 Chilean Cooking Class, Explore Valparaíso Valparaíso
Day 5 Valparaíso Street Art & City Walking Tour, Transfer to Santiago Santiago
Day 6 Cajón de Maipo Culture, Hiking & Village Tour Santiago
Day 7 Santiago City Tour, Depart  

Detailed Itinerary

Day 1: Arrive in Santiago, Transfer to Matetic Vineyards

Settle in at your boutique hotel nestled within Matetic Vineyards (photo courtesy of La Casona)

Welcome to Chile! Land in the frenetic capital, Santiago, where you'll meet your driver and journey an hour west to the lush Casablanca Valley, known worldwide for producing stellar white wines, from chardonnay to sauvignon blanc, pinot noir, and syrah varieties. Travel through the grape-vine-grooved countryside to Matetic Vineyards.

Check into your room at the vineyard's boutique hotel, La Casona, a yellow-hued country home that dates back to the 1900s. Now stylishly refurbished, you can expect lounges with roaring fireplaces and cozy rooms that overlook gardens dotted with lakes and towering palm trees, a pool, and a working farm, complete with alpacas. 

Spend the afternoon lounging by the pool or explore the vineyard's extensive hiking and horseback riding trails. End with dinner at the on-site Equilibrio Restaurant, which serves Chilean cuisine with a farm-to-fork ethos.  

Day 2: Casablanca Valley Wine Tour

Sample fine Chilean wines at renowned vineyards in the Casablanca Valley

Today, you'll delve into the Casablanca Valley's acclaimed viticulture with a private guide. Learn how the valley's strategic location near the Pacific coast is ideal for growing grapes, with sea breezes and fertile soil providing perfect conditions for them to thrive. 

Make a stop at Viña Casa Marín, a vineyard set on rolling hills above the tiny town of Lo Abarca, just a mile (1.6 km) from the ocean. Tour the grounds with a sommelier to learn about the production process and taste three varieties of their coveted wines. You'll also discover how Viña Casa Marín is famed for being one of Chile's first female-founded wineries. 

Return to your hotel next for a tour of Matetic Vineyards, where a guide will teach you about their biodynamic production techniques, and you'll get to taste their renowned organic wines. Soak up sweeping views of the valley as you wander the vineyards, then descend to the underground cellar for tastings. 

Day 3: Transfer to Valparaíso, Cultural Tour of Viña del Mar & Valparaíso

Explore the colorful, UNESCO-listed seaport of Valparaíso
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This morning, you'll travel an hour north to the Chilean coastal cities of Valparaíso and Viña del Mar. The first stop on your private tour is Viña del Mar, an upscale beach resort teeming with shopping boutiques, high-rise apartment blocks, and manicured gardens. These blend with striking landmarks like the Germanic Wulff Castle and the Venetian-Gothic Vergara Palace, where the founder of Viña del Mar once lived. 

Enjoy some of South America's best seafood at an ocean-front restaurant before moving on to the UNESCO-protected seaport of Valparaíso. The city is a throwback to the turn of the 20th century when electric trolleys coasted along the waterfront, and funicular elevators carried passengers to the city's highest points. 

Travel by trolley between Plaza Sotomayor and Plaza Aníbal Pinto, then board the Reina Victoria funicular for aerial city views. Ramble through hilly neighborhoods like Cerro Alegre, Cerro Concepción, and Cerro Florida, with their brightly-painted houses, old churches, and cobbled squares. In Cerro Florida, you'll get the chance to visit La Sebastiana, a museum once home to Nobel-Prize-winning Chilean poet Pablo Neruda. 

Afterward, check into the chic Fauna Hotel in Valparaíso, set in a restored building from 1870 in the ancient Cerro Alegre district. Highlights include a rooftop terrace and restaurant, which offers views over the city and the Bay of Valparaíso, and rooms featuring exposed brick walls, upcycled wooden floors, and contemporary art. 

Day 4: Chilean Cooking Class, Explore Valparaíso

Learn to make traditional Chilean dishes, like empanadas

Get a taste of Chile's beloved cuisine today with a small-group cooking class. Accompanied by an expert chef, you'll begin at one of Valparaíso's iconic street markets, picking up fresh ingredients. Back in the kitchen, the chef will teach you step-by-step how to make some of Chile's most famous dishes, from ceviche to empanadas, as well as signature pisco sours. 

After feasting on your creations, the rest of the day is yours to enjoy Valparaíso. Navigate the calf-busting streets and stop to sip coffee in cute street-side cafés. If you're craving some beach time, relax on nearby Concón Beach, or for a slice of serenity, simply chill out on the rooftop terrace of your hotel.

Day 5: Valparaíso Street Art & City Walking Tour, Transfer to Santiago

Admire vibrant murals on a Valparaíso street art tour

Spend your last morning in Valparaíso on a private street art and city walking tour. Join your knowledgeable local guide to traverse the city's steep streets on foot and by funicular, hearing about its history and spotting key landmarks. 

Along the way, you'll learn about the Valparaíso street art scene, which dates back to Pinochet's brutal rule, when artists painted in secret as an act of rebellion. When democracy was restored to Chile in 1990, the government made street art legal, and now colorful murals cover the city. Admire work by famous artists such as Inti, Cuellimangui, Sammy Espinoza, and Cynthia Aguilera. 

Afterward, take a private car 1.5 hours east back to Santiago and check into your boutique hotel, The Singular Santiago. Set in the trendy Lastarria neighborhood, the hotel hosts one of Santiago's top rooftop spaces, with a pool and a bar perfect for evening cocktails accompanied by views of the twinkling city skyline. Relax in the spa and then retire to your elegant room, with a marble bathroom and king-size bed dressed with Egyptian cotton sheets.  

Day 6: Cajón de Maipo Culture, Hiking & Village Tour

Discover the wild beauty of the Maipo Valley 

Escape the city today and head an hour and a half south to the wild Maipo Valley. Tackle winding mountain roads with a private guide, passing through villages where you'll glimpse slow-paced rural life. Stop in the small town of San José de Maipo, the launching pad for adventure sports enthusiasts who come to raft, hike, and climb in the region. 

Spend your day exploring the town's traditional squares and markets, then venture into the countryside for scenic hikes of this mountainous area, located deep in the Andes, home to mighty waterways and glaciers. At the end of the tour, you'll stop near a crashing waterfall for a lavish picnic before returning to the city for a final free evening in the capital. 

Day 7: Santiago City Tour, Depart

Tour Santiago's historic landmarks and hilltop viewpoints

This afternoon, get out and experience the pulse of Santiago with a private city tour. Start by wandering the aisles of Santiago's labyrinthine Mercado Central or Mercado La Vega. These markets are the beating heart of the city, overflowing with vendors and locals eager to get their hands on the day's produce. With the help of an English-speaking guide, engage with vendors and shoppers, sampling delicious tidbits along the way. 

Visit Plaza de Armas, located in Santiago's historic center. Founded in 1541, it's home to the impressive Catedral Metropolitana, a neoclassical church whose twin bell towers dominate the north side of the plaza. Finally, enjoy panoramic vistas from the hills of Cerro Santa Lucía Hill or Cerro San Cristóbal. Take in the urban sprawl and spot landmarks like the Gran Torre Costanera, the tallest building in Latin America. 

Savor a final meal in the bohemian Bellavista neighborhood before taking a private transfer to the airport in time for your homebound flight. Safe travels! 

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