5 days in Chile: Santiago, Valparaíso hills & Casablanca wine

Two days in Santiago's centre, Bellavista and Cerro San Cristóbal, a Casablanca Valley winery day on the road to the coast, then two days on Valparaíso's hills, funiculars and port. Best October to April; harvest season is March–April.

1. Day 19:45 am – 10 pm · 7 stops
2. 9:45 am 1

   Changing of the guard at La MonedaSantiago

   The presidential palace and Plaza de la Constitución in front. The changing of the guard runs every other day, at about 9:50 on weekdays and 10:50 on weekends and holidays: check the schedule the night before and arrive 15 minutes early (2026 trip report). The public areas are free; interior visits need online pre-registration.

   8 min walk · 650 m
3. 10:45 am 2

   Plaza de Armas and the cathedralSantiago

   The founding square, ringed by the Catedral Metropolitana, the National History Museum and the old Correos building. Walk there along the painted pedestrian Paseo Bandera, a five-minute detour that 2026 itineraries recommend. Free.

   3 min walk · 150 m
4. 11:30 am 3

   Museo Chileno de Arte PrecolombinoSantiago

   A compact, beautifully lit collection of textiles, ceramics and gold from across the Americas; about an hour is enough. Open Tuesday to Sunday 10:00–18:00 (last entry 17:30), closed Mondays. Foreign adults pay roughly CLP 14,000–16,000; confirm at the desk.

   8 min walk · 600 m
5. 1 pm 4

   Seafood lunch at the Mercado CentralSantiago

   The 1872 iron fish market is the classic Santiago seafood lunch. Reports agree: skip the touts and big restaurants in the middle, where a platter for two runs about CLP 50,000, and eat at the smaller stalls round the edge or one street over. Order a paila marina or machas a la parmesana.

   13 min walk · 1000 m
6. 3:15 pm 5

   Up Cerro Santa LucíaSantiago

   The hill where Santiago was founded, now a terraced park with fountains and a fort at the top. Steep zigzag paths but big views over the city to the Andes on a clear day. Usually open about 9:00–19:00; free.

   7 min walk · 500 m
7. 4:45 pm 6

   Lastarria and the Museo Nacional de Bellas ArtesSantiago

   The grand fine-arts museum sits in Parque Forestal, steps from Barrio Lastarria's bookshops and cafés; entry is free or nearly so. Both a 2026 trip report and the Argentine press's Santiago guide send you here for the calmer side of the centre.

   5 min walk · 400 m
8. 8 pm 7

   Chilean wine by the glass at BocanárizSantiago

   The Lastarria wine bar that food writers and a 2026 trip report both name: a long list of Chilean carménère and sauvignon blanc by the glass, with small plates to share. Book for a table; a couple of glasses and plates come to about CLP 35,000.

9. Day 210 am – 10 pm · 6 stops
10. 10 am 8

    Museo de la Memoria y los Derechos HumanosSantiago

    A sober, essential account of the 1973–1990 dictatorship, recommended by Santiago guides for anyone wanting to understand modern Chile. Free entry; allow 90 minutes. Check the opening days before you go.

    8 min by train or taxi · 4.2 km
11. 12:30 pm 9

    Lunch in BellavistaSantiago

    Bellavista's restaurant courtyard, a short walk from La Chascona. A 2026 trip report puts mains at CLP 12,000–18,000 and craft beer at CLP 6,000–8,000.

    4 min walk · 350 m
12. 2 pm 10

    La Chascona, Neruda's Santiago houseSantiago

    Pablo Neruda's ship-like house tucked under the hill, built for Matilde Urrutia. Open Tuesday to Sunday 10:00–18:00, closed Mondays and a few national holidays; CLP 9,500 for foreign adults (2026). Buy online in high season.

    3 min walk · 200 m
13. 3:30 pm 11

    Funicular up Cerro San CristóbalSantiago

    Ride the funicular from the top of Pío Nono to the Virgin statue for the classic Santiago-and-Andes view; round trip about CLP 6,000–8,000. The funicular runs daily; the teleférico across the park usually closes Mondays. Clear mornings after rain give the best mountain views.

    8 min by train or taxi · 3.0 km
14. 6:30 pm 12

    Sunset from Sky CostaneraSantiago

    The 300-metre observation deck on South America's tallest building. Go about 45 minutes before sunset, skip it on smoggy or cloudy days; about CLP 18,000–20,000 on site (2026).

    8 min by train or taxi · 1.7 km
15. 8:30 pm 13

    Dinner at LiguriaSantiago

    A loud, much-loved Santiago bistro-bar near metro Manuel Montt; travellers who lived in the city call it the place they went back to most. Order pollo al pil pil or osobuco with a pisco sour.

16. Day 39 am – 5:15 pm · 5 stops
17. 9 am 14

    Drive Route 68 to the Casablanca ValleySantiago

    Casablanca sits 75–80 km from Santiago on Route 68, the road to Valparaíso, about 1h15 by car. Rent a car or hire a driver for the day so nobody has to drive after tastings; a first-hand report found a driver with a van for under US$100 a day for a group.

18. 10:30 am 15

    Organic tour and tasting at Viña EmilianaCasablanca

    One of the world's largest organic and biodynamic vineyards, with gardens and animals; every Casablanca report includes it. Tours run around 10:30 and 14:30 and need booking a week ahead; a classic tour with a 3–4 wine tasting runs about CLP 15,000–20,000.

    13 min by train or taxi · 13 km
19. 12:30 pm 16

    Lunch at Tanino, Casas del BosqueCasablanca

    The vineyard restaurant that winery tours and travellers both pick for lunch, with terrace seating over the vines and blankets on cool days. Pair the house sauvignon blanc with seafood or meat; book ahead on weekends.

    14 min by train or taxi · 14 km
20. 3 pm 17

    Tasting at Casona VeramonteCasablanca

    A big Route 68 winery with a hacienda-style casona; travellers short on time just do a tasting here, while full visits add a viewpoint hike or vineyard cycling. Book on the winery's site.

21. 4:15 pm 18

    On to ValparaísoCasablanca

    Another 45–60 minutes down Route 68 to the coast. Sleep on Cerro Alegre or Cerro Concepción so the next two days start on foot.

22. Day 49:30 am – 9:30 pm · 6 stops
23. 9:30 am 19

    Ascensor El Peral up from Plaza SotomayorValparaíso

    Start at Plaza Sotomayor and ride the century-old El Peral funicular from Plaza de la Justicia up to Cerro Alegre, as Chile's tourism board route does. The fare is a few hundred pesos.

    3 min walk · 100 m
24. 10 am 20

    Paseo Yugoslavo and Palacio BaburizzaValparaíso

    The art-nouveau mansion at the top of El Peral now holds the city's fine-arts museum; the Paseo Yugoslavo terrace outside has one of the best bay views on Cerro Alegre.

    3 min walk · 250 m
25. 11:30 am 21

    Paseo Gervasoni and Cerro ConcepciónValparaíso

    Cross to Cerro Concepción for the Paseo Gervasoni lookout over the port and the red-roofed Lutheran church nearby. Free; this is the heart of the UNESCO-listed historic quarter.

    5 min walk · 400 m
26. 1 pm 22

    Lunch on Cerro AlegreValparaíso

    The two hills are packed with small cafés and set-lunch places with terraces; pick whichever has a free table with a view.

    4 min walk · 300 m
27. 2:30 pm 23

    Murals of Paseo Dimalow, Paseo Atkinson and the Piano StaircaseValparaíso

    Wander the street-art lanes and stairways that the official two-day route strings together: Paseo Dimalow, Paseo Atkinson's balconies and the Piano Staircase. A free tip-based walking tour covers the same ground if you want the stories behind the murals.

    3 min walk · 200 m
28. 7:30 pm 24

    Dinner at La ConcepciónValparaíso

    A long-running Cerro Concepción restaurant with a bay-view terrace, seafood and fish, and a 45-label wine list (Meteored Chile, 2025). Book a terrace table for sunset.

29. Day 510 am – 6:15 pm · 4 stops
30. 10 am 25

    La Sebastiana, Neruda's Valparaíso houseValparaíso

    Neruda's tall, narrow house stacked up Cerro Bellavista, with the best window over the bay. About CLP 9,500 including a 40–50 minute audio guide in English; Tuesday to Sunday 10:00–18:00, closed Mondays. A taxi from the flat takes 5–10 minutes.

    8 min by train or taxi · 3.8 km
31. 12 pm 26

    Seafood and sea lions at Caleta PortalesValparaíso

    The working fishing cove 20 minutes along the shore, where Chile's tourism board sends visitors for a seafood lunch with sea lions lounging by the boats. Simple fried fish and empanadas de mariscos.

    8 min by train or taxi · 3.4 km
32. 2:30 pm 27

    Bay boat ride from Muelle PratValparaíso

    The lancheros of Muelle Prat run short loops around the bay past the navy ships and container cranes, a tradition the city recognises as heritage. Agree the price before boarding.

    8 min by train or taxi · 2.2 km
33. 4:30 pm 28

    Bus back to SantiagoValparaíso

    Frequent buses run to Santiago in about 1h45 (or return the hire car); allow extra time on Sunday evenings when everyone heads back.