Begin your adventure in Santiago, and explore the colorful city of Valparaiso, and take in the sights and sounds of the modern metropolis. Next, head to the coast for a tour of the colorful city of Valparaiso accompanied by wine tasting in the Casablanca Valley. Then, Head out to the mountains to hit the slopes at the world-renowned Portillo Ski Resort. Spend several days testing your skills on the slopes, followed by evenings of relaxing at the spa or dining at the resort's fine restaurants.


  • Stroll the colorful streets of coastal Valparaiso, a UNESCO World Heritage Site
  • Go wine tasting in Chile's famous Casablanca Valley
  • Visit the world-renowned Portillo Ski Resort, and test your skills on the slopes

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Santiago de Chile Santiago
Day 2 Santiago to Valparaiso & Wine Tour Santiago
Day 3 Santiago de Chile - Portillo Ski Resort Portillo
Days 4-7 Portillo Ski Resort Portillo
Day 8 Portillo Ski Resort - Santiago & Departure  

Detailed Itinerary

Day 1: Arrival in Santiago de Chile

Hike or take a gondola up to the top of Cerro San Cristobal
Hike or take a gondola up to the top of Cerro San Cristobal

Welcome to Chile! Upon arrival at Santiago International Airport, a driver will meet you and transfer you to your hotel. You'll have the rest of the day to explore the city at your leisure. 

Suggested activities include:

  • Hike to the top of Cerro San Cristobal, where you can get your bearings by surveying the area from a high vantage point. Pathways lead 2,788 feet (850 m) up this central hill to a series of lookouts that offer wraparound views of Santiago. If you aren't the hiking type, not to worry: catch a scenic gondola instead.

  • Stroll the cobblestone streets of Barrio Bellavista. On the north side of Santiago, you'll find this trendy enclave, at once fashionable and bohemian. Stroll past colorful houses adorned with graffiti art and choose between an eclectic array of eateries and bars—great for people watching. 

  • Visit the Plaza de Armas, a stone plaza located in Santiago's historic center dating to 1541. There's also the impressive Catedral Metropolitana, a neoclassical church dating to 1748 whose towering twin bell towers dominate the north side of the plaza.

  • Snap pics in front of the Palacio de la Moneda. Chile's opulent Presidential Palace (known simply as "La Moneda") is a short stroll from the Plaza de Armas. It was here in 1973 that Chile's armed forces, backed by the U.S. government, overthrew President Salvador Allende, kicking off a brutal right-wing military dictatorship that would last for 17 years. Visitors are welcome.

For dinner be sure to get out of the hotel and enjoy a culinary adventure in the city. In recent years Santiago has emerged as a global foodie destination. Chilean chefs are reinventing traditional dishes like empanadas, cazuelas (stews), and seafood with ingredients harvested all the way from the northern deserts and southern Patagonian regions. You can find great restaurants and wine bars not only in the Bellavista neighborhood but also in the revitalized historic barrios of Yungay and Italia.

Day 2: Santiago to Valparaiso & Wine Tour

Colorful Valparaiso
Colorful Valparaiso

After breakfast, you will depart from your hotel bound for the historic Chilean coastal city of Valparaiso. This is a special treat because Valparaiso is not only a UNESCO World Heritage Site, it's also the most romantic and artistic city in the country. 

But that's not all. En route you will stop at an organic winery in the Casablanca Valley for a guided tour and tasting. The owners of the Emiliana Winery pride themselves on their all-natural approach to growing grapes, which utilizes the combined efforts of plants and livestock to help fertilize the crops. You'll tour the vineyard and the production facilities and then taste four different wines paired with local cheeses and chocolates. 

Shortly after the tour, you'll arrive in Valparaiso. This colorful, well-preserved seaport is a throwback to the turn of the 20th century when electric trollies coasted along the waterfront and lurching funicular elevators carried passengers to the highest points in the city. The tour of Valparaiso begins at the port, where you'll travel by trolley between Plaza Sotomayor and Plaza Aníbal Pinto. Then it's time to hop in the Reina Victoria funicular and ascend to the top, where you'll be greeted with panoramic views of the city.

You'll then wander the high streets through hilly neighborhoods like Cerro Alegre, Cerro Concepción, and Cerro Florida. This is the best way to get to know Valparaiso, as there's nothing quite like strolling among the brightly painted houses, old churches, and cobbled squares that comprise this city. And no matter where you happen to be, you can always find sweeping views of the Pacific coast and the blanket of blue water running out to the horizon. Valparaiso is like San Francisco reimagined by Dr. Seuss.   

After the tour, you can enjoy an optional lunch in a local restaurant (try the seafood; it's some of the best in South America). Then it's time to hop back in the minivan, transfer back to Santiago, and return to your hotel.

Tour Duration: Full day

Plan your trip to Chile
Chat with a local specialist who can help organize your trip.

Day 3: Santiago de Chile - Portillo Ski Resort

After breakfast, you will be taken to the Portillo Ski Resort, located 100 miles northeast of Santiago. Nestled among the Andes at 8,360 feet above sea level, Portillo Ski Center offers skiers of all levels a boutique ski experience. The resort offers skiing and snowboarding lessons for beginners of all ages, and more advanced skiers will feel right at home on the more challenging slopes.

Days 4-7: Portillo Ski Resort

Enjoy Portillo Ski Center's all-inclusive program, including four daily meals, unlimited access to the slopes and all the facilities. Explore the center and its first-class facilities: 14 rope bridges, 35 pistes (groomed trails), and two square miles of land.

After a long day on the slopes, relax in the heated swimming pool, sauna, and jacuzzi. Try a yoga class, or pamper yourself with a massage. In the evening, enjoy beautiful views of the Andes mountains while dining in the on-site restaurant or enjoying a drink in a cozy bar.

Day 8: Portillo Ski Resort - Santiago & Departure

Sunset in Santiago
Sunset in Santiago

After breakfast, head back to the Santiago Airport for your return flight home. ¡Buen viaje!


Map of Ski Portillo, Santiago & Valparaiso - 8 Days
Map of Ski Portillo, Santiago & Valparaiso - 8 Days