If you want to experience some of the highlights of the Santiago region but are strapped for time, then this quick four-day trip is perfect for you. Arrive in Santiago, and take in the major sights during a full-day walking tour. Then it's off to the coast for some wine tasting and an exploration of the most romantic city in the nation: Valparaiso. Take your time to explore the colorful streets and take in cit city's artsy vibe before returning to Santiago for the evening.

Highlights

  • Explore the streets of Santiago, Chile's cosmopolitan capital
  • Tour Valparaiso, the most romantic and artistic city in Chile
  • Go wine tasting in Chile's famous Casablanca Valley

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Santiago de Chile Santiago
Day 2 Santiago City Tour Santiago
Day 3 Valparaiso, Viña del Mar & Casablanca Valley Santiago
Day 4 Departing Santiago  

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 City Tour

Santiago's bustling central market
Santiago's bustling central market

Like any great city, Santiago's cultural pulse is found in its people, marketplaces, and cuisine. To that end, today you'll head out on a guided city tour. Depending on your preference, this will either be a full-day or half-day tour with an English-speaking guide. Regardless of which one you choose, you'll become an honorary Santiaguino!

Tour highlights:

  • Wander the aisles of Santiago's labyrinthine Mercado Central and Mercado La Vega. These markets are the beating heart of the city, overflowing with vendors and local residents eager to get their hands on the day's fresh produce. 
  • Visit the Catedral Metropolitana, a neoclassical church dating to 1748 and whose towering twin bell towers dominate the north side of the plaza.

  • Head to the glittering Costanera Center, an epic skyscraper encased in glass! For one of the best and certainly highest views in Latin America, go to the Sky viewpoint. At nearly 1,000 feet (304 m) high, the top offers 360-degree views of the city below, as well as the surrounding Andes.

  • Visit Cerro Santa Lucia, a small, manicured park in the center of Santiago. As you stroll up the hill, make sure to stop and see Fuente Neptuno and Castillo Hidalgo, two impressive structures located within the grounds. 

  • If you haven't done it yet, ascend to the top of Cerro San Cristóbal via hike or cable car. Enjoy the 360° panoramas and take plenty of photos, as these are the most incredible views in Santiago.

Day 3: Valparaiso, Viña del Mar & Casablanca Valley

Visit a winery in Chile's beautiful Casablanca Valley
Visit a winery in Chile's beautiful Casablanca Valley

After breakfast, you'll depart from your hotel in Santiago and drive about an hour west towards the coast. Your destination is the Casablanca Valley, which is home to many top wineries. Here you'll take a tour, tasting, and enjoy lunch at the wonderful Casa del Bosque Winery.

After lunch, you'll continue the short distance to the coast and the cities of Valparaiso and Viña del Mar. First up is the port city of Valparaiso, a UNESCO World Heritage Site famous for its colorful hillside neighborhoods, winding stairways, and abundance of street art. It's a throwback to a time when electric trollies coasted along the waterfront and funicular elevators carried people high into the hills. On a city tour, you'll visit some famous sites, such as Plaza de la Victoria and the Naval Academy, and ride a funicular high into the hills where panoramic vistas of the bay await. A real highlight is visiting the former home of Chile's Nobel Prize-winning poet, Pablo Neruda. 

Afterward, you'll drive a short way to the adjacent town of Viña del Mar, which couldn't be more different in terms of style than its neighbor. Whereas Valparaiso is a retro artistic haven, Viña is a modern seaside hotspot abounding with sleek shopping centers and upscale restaurants. After touring around the city and waterfront, you'll return to Santiago in time for dinner.

Day 4: Departing Santiago

Sunset over Santiago
Sunset over Santiago

It's time to say farewell to Chile. In the morning, you'll transfer from your hotel to the airport in Santiago for your flight back home. ¡Buen viaje!

Map

Map of Santiago & Valparaíso Exploration - 4 Days
Map of Santiago & Valparaíso Exploration - 4 Days
Deborah
Written by Deborah Hayman, updated Mar 18, 2019