Santiago de Chile 5-Day Itinerary: Downtown, Valparaíso and Wine Country

About 800 meters on foot from Plaza de Armas, La Moneda Palace has been the seat of the Chilean government since the early 19th century, originally built as a colonial mint. The changing of the presidential guard happens every other day in the inner courtyard, and the civic square in front of the palace often hosts free cultural events and performances.

The underground La Moneda Cultural Center, with a separate entrance, runs temporary art exhibitions that are free most days, worth checking the schedule before heading over.

Plaza de Armas has been Santiago's founding point since 1541, surrounded by the Metropolitan Cathedral, the Central Post Office and the National History Museum. The cathedral, with a neoclassical facade and baroque interior, is the seat of the Archdiocese of Santiago and holds one of Chile's richest silver altars.

The square is also where street performers, traditional shoeshiners and roasted peanut vendors gather, a good snapshot of downtown Chilean life in the late afternoon. Set aside about an hour here before walking to the next stop.

A short staircase climb leads to the top of this volcanic-origin hill right in the middle of downtown, with fountains, gardens and a replica medieval castle built in the 19th century. It's a quick 15 to 20 minute stop, but the lookout at the top delivers one of the best views over downtown Santiago with the Andes in the background, especially near late afternoon.

Valparaíso is about an hour and a half by car or bus from Santiago and has been a UNESCO World Heritage Site since 2003, thanks to its hills covered in colorful houses and zigzagging streets. Century-old funiculars, like the Concepción and Reina Victoria lifts, are the traditional way up Cerro Concepción and Cerro Alegre, now filled with street art, cafés and informal viewpoints tucked between the houses.

It's worth spending the whole morning walking these two hills without rushing. Those who want more can round it off at La Sebastiana House Museum, one of Pablo Neruda's three houses in Chile, with a bay view from the fourth floor where the poet used to write, a short walk from the main circuit.

About 15 minutes from Valparaíso, Viña del Mar is Chile's most traditional beach town, with urban beaches, tall buildings along the shore and the Flower Clock, a working clock from 1962 planted with live flowers, built for a World Cup. Castillo Wulff and the Presidential Castle, two early 20th-century seaside mansions, round off an easy stroll along the waterfront.

The afternoon works well here before heading back to Santiago: the promenade is flat and easy to walk, with seafood options cheaper than in Santiago, given how close it sits to the fishing port.

San Cristóbal Hill is Santiago's second-tallest hill and its most complete lookout point, surrounded by Metropolitan Park and topped by a 14-meter statue of the Immaculate Virgin, raised in 1908. The funicular that climbs from the Bellavista neighborhood takes about 8 minutes and is the most traditional way up, though a cable car from Pedro de Valdivia Norte also runs.

On clear days, the view from the top stretches to the snow-capped Andes behind the entire city. Set aside at least two hours counting the funicular line, the ride up and time at the viewpoint.

Bellavista is the bohemian neighborhood at the base of San Cristóbal Hill, with rows of old houses painted in bold colors, murals and the city's biggest concentration of casual bars and restaurants. It's also home to La Chascona, the house Pablo Neruda built for his wife Matilde Urrutia, now a museum with gardens spread across different levels and objects the poet collected on his travels.

It's worth wandering Constitución and Dardignac streets, the heart of the neighborhood, before or after visiting La Chascona.

Lastarria is a small, culturally dense neighborhood, home to the National Museum of Fine Arts, with a neoclassical facade, columns and a glass dome, running since 1910 inside Forestal Park. A quick look at the facade and the surrounding bookshops and cafés fits into 20 to 30 minutes between other stops of the day.

A short walk from Lastarria and Plaza de Armas, the Municipal Theatre of Santiago has been Chile's main opera and ballet house since 1857, with a classic facade worth a photo even without catching a show. A quick 10 to 15 minute stop on the way between neighborhoods.

The Maipo Valley is the closest wine region to Santiago, about 40 minutes from downtown, internationally known for its Cabernet Sauvignon. Traditional wineries like Concha y Toro, in Pirque, run guided tours through their historic cellars and the Casa del Diablo, tasting included, with no need for your own car since most tours arrange transport straight from downtown.

A half-day tour, including transport, the visit and tasting, usually runs 3 to 4 hours, leaving the afternoon free for the rest of the day.

Back downtown, Sky Costanera is the observation deck on floors 61 and 62 of Gran Torre Costanera, the tallest building in South America at 300 meters. The 360-degree view shows all of Santiago ringed by the Andes, including San Cristóbal Hill seen from above.

Late afternoon, close to sunset, is the busiest and also the most beautiful time to go, worth buying tickets online in advance to skip the line.

In the Vitacura neighborhood, Bicentenario Park is a 30-hectare urban park along the Mapocho River, far calmer than the historic center, with lagoons home to free-living Chilean flamingos, bike paths and picnic areas. It's the ideal way to close out a busier itinerary: a quiet morning walk before heading to the airport.

The park sits about 25 minutes from Arturo Merino Benítez International Airport, a comfortable option for anyone flying out in the afternoon or evening on the last day.

A ten-minute walk from Bicentenario Park, still in Vitacura, the Ralli Museum is the one almost nobody puts on the itinerary and should. Entry is free, and the collection holds Dalí, Chagall, Miró and a strong room of contemporary Latin American art, spread through high-ceilinged galleries around a courtyard.

It works as a closing stop precisely because it is quiet: on a weekday it is often nearly empty, the visit takes an hour, and it sits on the way back to the airport. Just check the opening hours first, because it closes on Mondays and for the whole of February.