Santiago Chile 5 Day Itinerary

Five days based in Santiago de Chile is enough to run this region’s whole loop once: a light city anchor, a full day in Maipo wine country, a full day up in the Andes, a full day out at the coast, and a last day at a second, cooler-climate wine valley on the way back from the sea. If centro, the cerros, and Bellavista are the actual draw, our Santiago 5 day itinerary covers the city on its own terms instead of using it as a launchpad. Prices run in Chilean pesos, CLP, roughly 925-950 to the US dollar in 2026. Santiago itself sits at a flat 520 meters; the only altitude that matters all week is El Yeso’s 2,500.

Book these before you go:

Day Focus Travel time Rough daily cost (CLP)
1 Centro, plus Sky Costanera for orientation On foot and metro 40,000-55,000
2 Concha y Toro, Maipo Valley wine 45-60 min each way to Pirque 75,000-95,000
3 Cajon del Maipo, El Yeso Reservoir About 90 min each way 55,000-70,000
4 Valparaiso, Vina del Mar, La Sebastiana About 90 min each way by bus 45,000-65,000
5 Casablanca wine, Isla Negra About 60-75 min each way 70,000-90,000

Day 1: A Light City Anchor

Keep day one short on purpose, the rest of this week goes outward. Walk Plaza de Armas and the cathedral in the morning, free, then La Moneda’s exterior on Plaza de la Constitucion for the changing of the guard if the schedule lines up (it alternates by month). In the afternoon go up Sky Costanera , the observation deck on floors 61 and 62 of the Gran Torre, the tallest tower in South America, for the view that frames the whole week: the Andes to the east, where Cajon del Maipo and El Yeso sit, the Maipo and Casablanca valleys further out, and the coast beyond them. Adult entry runs roughly CLP 18,000-20,000.

Day 2: Concha y Toro and the Maipo Valley

Concha y Toro in Pirque is 45 to 60 minutes from central Santiago and the easiest wine-country stop this region has: a historic estate, the Casillero del Diablo cellar experience, and four tastings on the premium tour, roughly CLP 76,000 with transport included. Confirm current tour times directly at conchaytoro.com before booking through a reseller. Santa Rita sits close enough to pair as an afternoon extension if the day allows, but one winery done well beats two rushed ones on a trip with four more days to cover. This is the same Maipo day that anchors our 2 day itinerary ; five days just means you are not stuck stopping there.

Day 3: Cajon del Maipo, El Yeso Reservoir, and the Andes

This is the day that makes basing yourself in Santiago worth it over a city-only trip. Cajon del Maipo runs about 90 minutes up from the city into real Andes scenery, hot springs along the way, and the turquoise El Yeso reservoir at roughly 2,500 meters, the one stretch of this whole week where the altitude is worth noticing on a short walk. Full-day tours with transport and a picnic run roughly CLP 41,000-70,000pp and leave the hotel early, 5 to 6:30am, to beat both the crowds and the afternoon cloud buildup around the peaks. Stack this day onto the two above and you have our 3 day itinerary in full.

Day 4: Valparaiso, Vina del Mar, and La Sebastiana

Turbus and Pullman Bus run from Terminal Alameda every 15 to 30 minutes starting around 6am, roughly 90 minutes each way for about USD 8-15. Valparaiso’s hillside streets, covered in murals and stitched together by century-old funiculars, are the actual reason for the day; La Sebastiana , Pablo Neruda’s house above the port, is worth the detour on the way through. Vina del Mar next door is calmer and beach-oriented, an hour is plenty unless swimming is the point. Catch a bus back by 5 or 6pm, the later departures thin out fast and a missed one turns into an expensive taxi. Stop here and you have our 4 day itinerary ; day five below adds one more valley on top.

Day 5: Casablanca Wine and Isla Negra (or Pomaire, If the Wine Has Worn You Out)

Casablanca sits on the road back from the coast, a genuinely different, cooler-climate valley from Maipo, built around Sauvignon Blanc and Pinot Noir rather than the reds Concha y Toro poured on day two. Pair it with Isla Negra, the third and most dramatic of Neruda’s houses, built into the rocks above the ocean, roughly CLP 11,000, since it sits directly on the same coast road and costs nothing extra in travel time. If two wine days in one week feels like one too many, swap in Pomaire instead, the pottery town west of the city, but only with a tour or a rental car; the public transit route through Terminal San Borja and a Melipilla-bound bus eats 5 to 6 hours round trip for what a car covers in half that.

Casablanca or Pomaire on Day Five?

Casablanca wins for most travelers on this itinerary because day two already proved the wine angle works, and Casablanca’s cooler-climate whites are different enough from Maipo’s reds to justify a second wine day, with Isla Negra riding along for free on the same road. Pomaire only wins if wine specifically, not day trips generally, is what has worn thin by day five, and even then it needs a tour or a car to be worth the awkward transit out.

Should Valparaiso Be a Day Trip or an Overnight?

Honestly, an overnight suits Valparaiso better. Its steep, tangled streets and street art read differently at golden hour and after dark than in the middle of a coach-tour afternoon. A five day itinerary built around Santiago as a base rarely has a spare night to give it, though, so this plan keeps it a day trip. If Valparaiso is the actual priority, cut Casablanca on day five and stay over instead.

Do You Need a Car for This Itinerary?

No, and renting one adds more hassle than it saves across five day trips heading in four different directions. Tours with transport handle Cajon del Maipo and Casablanca, the bus covers Valparaiso better than driving into an unfamiliar coastal city would, and Concha y Toro tours run the same way. A car only earns its cost if Pomaire replaces Casablanca on day five, since that is the one leg public transit genuinely struggles with.

Before You Go

This is Santiago de Chile, the capital, not Compostela and not Cuba, and the currency is the Chilean peso, not the Argentine peso next door. Seasons run reversed from the Northern Hemisphere: January is summer, July is winter and ski season in the same Andes visible from El Yeso, and Santiago’s own winter brings a valley-basin smog that thins out the Andes views from the city itself, even while the mountains stay clear. Chile carries a US State Department Level 2 advisory, and the UK Foreign Office describes muggings as frequent in both Santiago and Valparaiso, increasingly with weapons. Avoid any demonstration near Plaza Italia, especially Friday evenings, and book taxis or rideshare rather than hailing one on the street after dark. If two, three, or four days is closer to the real budget, this same trip scales down cleanly, see the 2 day , 3 day , or 4 day versions. For a sixth or seventh day, see the 7 day itinerary instead.