Santiago + Wine + Valparaíso + the Andes — 5 Days

Activities

1. 09:00 Plaza de Armas & the colonial Centro 2h30

   Start in the 1541 colonial heart — Plaza de Armas with the Metropolitan Cathedral, the Casa Colorada, and street life. Nearby, La Moneda presidential palace (where the 1973 coup unfolded) and the Museo Chileno de Arte Precolombino, the region's finest pre-Columbian collection (~CLP 7,000 / $8).

   Cost: Free (Pre-Columbian Museum ~CLP 7,000 / $8) TIP: Do the Centro by day — it empties and feels less safe after dark. Keep your phone secured against snatching in the crowds. La Moneda's courtyard is free; the Pre-Columbian Museum is closed Mondays. A walkable, history-rich start.
2. 12:00 Mercado Central — seafood lunch 1h30

   Lunch at the grand 19th-century iron-framed fish market. Donde Augusto and the stalls serve caldillo de congrio (Neruda's beloved eel soup), machas a la parmesana, and ceviche. Grab a famous empanada de pino from Emporio Zunino on the corner.

   Cost: CLP 12,000-25,000 ($13-27) per person TIP: The market touts are pushy — settle on a restaurant and confirm prices before sitting. Caldillo de congrio and machas a la parmesana are the orders. Emporio Zunino's empanadas (CLP 2,800-3,800) are a quick add-on. Cash plus cards.
3. 14:30 Lastarria & Cerro Santa Lucía 1h30

   Wander the boutique Lastarria quarter — cafés, wine bars, museums, and the leafy Cerro Santa Lucía, a small hill-park with viewpoints in the middle of the city. A relaxed, atmospheric stretch and a good coffee or Emporio La Rosa ice-cream break.

   Cost: Free (ice cream CLP 2,800-5,000) TIP: Lastarria is the most walkable, characterful part of central Santiago — good for a slow afternoon. Cerro Santa Lucía's terraces are free. Emporio La Rosa on the corner does acclaimed rose and native-fruit ice cream. Easy by Metro (Universidad Católica).
4. 16:30 Cerro San Cristóbal — funicular & city panorama 1h30

   Take the historic funicular (~CLP 3,500 / $4) up the 300m hill to the white Virgin Mary statue and Santiago's best panorama, with the Andes behind. A cable car runs the ridge; paths descend through Parque Metropolitano toward Bellavista.

   Cost: ~CLP 3,500 ($4) funicular TIP: Time it for late afternoon into sunset (around 7:30pm summer, 6pm winter), when the Andes glow gold. Go on a clear day — winter smog can flatten the view. Funicular up, walk or cable car down toward Bellavista for the evening.
5. 19:30 Bellavista, La Chascona & Sky Costanera sunset 2h

   Descend into Bellavista, the bohemian Neruda quarter. Tour La Chascona, Pablo Neruda's quirky house-museum (~CLP 8,000 / $9). Then head to Sky Costanera, the deck atop South America's tallest building, for the sunset skyline (~CLP 12,000-15,000).

   Cost: La Chascona ~CLP 8,000; Sky Costanera ~CLP 12,000-15,000 TIP: La Chascona closes in the early evening, so see it before sunset, then do Sky Costanera or save the deck for another clear evening. Sky Costanera (Tobalaba Metro) is best at golden hour on a clear day. Bellavista comes alive for dinner and nightlife after.
6. 21:30 Dinner — Chilean classics in Bellavista 2h

   Dinner at Galindo, a Bellavista institution in an old adobe house, for pastel de choclo (sweet-corn-topped pie) and cazuela, or stay in Lastarria for a wine flight at Bocanáriz and a pisco sour at Chipe Libre.

   Cost: CLP 15,000-30,000 ($16-32) per person TIP: Galindo's pastel de choclo is the classic order; the terrace fills early. Chileans dine late (9-10pm). Bellavista's bars buzz Thursday-Saturday — fun but keep your wits late at night. Use Uber/Cabify to get home. Cards accepted.

Meal Recommendations

Activities

1. 09:00 Depart for the wine valley 1h

   Head to the Maipo Valley (Carmenère and Cabernet, ~45 min south) or the cooler Casablanca Valley (Sauvignon Blanc and Pinot Noir, on the Valparaíso road). A guided tour ($80-120) with transport, two wineries, tastings, and lunch is easiest since you'll be drinking.

   Cost: Tour $80-120 (incl. tastings & lunch) TIP: A tour removes the drink-and-drive problem and includes transport. Concha y Toro in Maipo is reachable by Metro to Las Mercedes plus a taxi if you'd rather go independent. Book winery tastings ahead, especially in autumn (Mar-May) harvest.
2. 10:30 First winery — tour & tasting 2h

   Tour your first estate — for Maipo, Concha y Toro (Chile's largest, home of Casillero del Diablo) is the famous, polished option; Cousiño-Macul and Santa Rita are more historic. Walk the vineyards with the Andes behind, see the cellars, and taste several wines.

   Cost: Included in tour (~CLP 20,000-35,000 if solo) TIP: Concha y Toro's 'Casillero del Diablo' (Devil's Cellar) legend is touristy but fun; smaller estates feel more authentic. Carmenère — once mistaken for Merlot, rediscovered in Chile in 1994 — is the signature Maipo grape to taste here.
3. 13:00 Lunch among the vines 1h30

   Lunch at the winery restaurant or a nearby spot — grilled meats, Chilean dishes, and of course the estate's wines, often on a terrace facing the vineyards and the mountains.

   Cost: Included or CLP 15,000-30,000 ($16-32) TIP: Vineyard lunches pair local wine with hearty Chilean cooking. Pace the tastings — Chilean reds are generous. Take photos of the Andes-backed vines, a classic Maipo image.
4. 15:00 Second winery & return 3h

   Visit a second, often smaller boutique estate for a contrasting style and tasting, then return to Santiago by late afternoon. In Casablanca, the cool-climate whites (Sauvignon Blanc) and Pinot Noir are the highlight.

   Cost: Included in tour TIP: A second, smaller winery balances the big-name first stop. Buy a bottle or two at the cellar door — Chilean wine is excellent value at source. Back in the city for a relaxed evening.
5. 20:00 Evening in Lastarria — wine bar & dinner 2h30

   Round off a wine day in Lastarria — a flight at Bocanáriz comparing valleys you didn't visit, or a pisco sour at Chipe Libre, then a relaxed dinner. Or splurge on Boragó (Vitacura) or Ambrosía (Providencia) if booked ahead.

   Cost: CLP 20,000-45,000 ($21-48) per person TIP: Bocanáriz's flights are a perfect coda to a winery day. Boragó (No. 23 World's 50 Best 2025) and Ambrosía both need reservations well ahead. Lastarria is walkable and safe in the evening. Cards accepted.

Meal Recommendations

Activities

1. 08:30 Travel to Valparaíso 1h45

   Head about 1.5 hours west to the Pacific coast. The cheapest route is an intercity bus from Pajaritos or the main terminal (Turbus, Pullman), CLP 3,000-4,500 ($3-5) each way; a guided day tour ($70-90) adds Casablanca wine en route.

   Cost: Bus CLP 3,000-4,500 each way / tour $70-90 TIP: Buses are frequent and cheap; a tour bundles transport, a guide, and often a Casablanca winery stop. Sit on the right for coastal views nearing Valparaíso. Allow a full day to do the hills justice.
2. 10:30 Valparaíso cerros, funiculars & street art 2h30

   Explore the UNESCO World Heritage port's hills (cerros) — Concepción and Alegre are the prettiest — riding the century-old funiculars (ascensores) up steep slopes lined with brightly painted houses and world-famous street art and murals.

   Cost: Funiculars ~CLP 500-1,000 each; murals free TIP: Cerros Concepción and Alegre have the best-kept color, cafés, and viewpoints. The funiculars are an experience in themselves. Wear good shoes for the steep, cobbled lanes, and watch your phone and bag — Valparaíso has petty theft.
3. 13:00 Lunch with a harbor view 1h30

   Lunch on the hills — Valparaíso has excellent seafood and creative bistros with sweeping port views. Fresh fish, ceviche, and a Casablanca Sauvignon Blanc, looking out over the cranes and colorful rooftops.

   Cost: CLP 12,000-25,000 ($13-27) per person TIP: The Concepción/Alegre restaurants have the best views and food. Seafood and cool-climate whites are the move on the coast. A relaxed midday break before the afternoon.
4. 15:00 La Sebastiana — Neruda's hilltop house 1h30

   Visit La Sebastiana, Pablo Neruda's whimsical Valparaíso house-museum (~CLP 8,000 / $9), perched on a hill with panoramic windows over the bay — full of his nautical collections and one of three Neruda houses (with La Chascona and Isla Negra).

   Cost: ~CLP 8,000 ($9) TIP: The bay views from La Sebastiana are the highlight, alongside Neruda's eccentric collections. Pairs with La Chascona seen on Day 1 for the full Neruda picture. Audio guides explain the rooms well.
5. 17:00 Viña del Mar coast & return 3h

   Optionally hop to neighboring Viña del Mar — beaches, the flower clock, and the casino — for a contrasting, modern seaside feel, then return to Santiago in the evening (about 1.5-2 hours).

   Cost: Local transport CLP 500-1,500 + return bus TIP: Viña is a short metro-train (Merval) or bus from Valparaíso — beachy and polished versus Valparaíso's gritty charm. Confirm your return bus time; evening services are frequent but fill up. Back in Santiago for a final night.

Meal Recommendations

Activities

1. 08:00 Into the Andes 2h

   Head east into the mountains. In the warmer months, the Cajón del Maipo canyon (1.5-2 hours southeast) for alpine scenery; in winter (Jun-Sep), the ski resorts (Valle Nevado, El Colorado ~1.5-2h; Portillo ~2.5-3h). A guided transfer/tour avoids the switchback mountain driving.

   Cost: Cajón del Maipo tour $60-100 / ski transfer $40-80 TIP: Let a tour or transfer handle the hairpin roads (chains are required on the ski road in winter). Cajón del Maipo runs roughly Oct-Apr for hiking; ski season is Jun-Sep. Decide by your travel month — the seasons are flipped here.
2. 10:30 Embalse del Yeso & canyon scenery (summer) — or skiing (winter) 3h

   In summer, reach the turquoise Embalse del Yeso reservoir, framed by Andean peaks — a spectacular high-altitude lake and the canyon's signature sight. In winter, hit the slopes at Valle Nevado or Portillo, skiing with the Andes all around.

   Cost: Reservoir free (in tour) / lift ticket ~$50-90 TIP: Embalse del Yeso is the postcard image of Cajón del Maipo — the road in is rough, hence a tour. Skiers should bring or rent gear at the resort; altitude (3,000m+) can be felt. Either way, layer up — mountain weather shifts fast.
3. 14:00 Hot springs or mountain lunch 2h30

   In summer, soak at the Termas Valle de Colina hot springs higher in the canyon, or lunch at a mountain spot. In winter, lunch at the resort base before an afternoon run or the ride down.

   Cost: Termas ~CLP 15,000 ($16) / resort lunch varies TIP: The Termas Valle de Colina terraced thermal pools are a Cajón del Maipo highlight (bring a swimsuit and towel). At the ski resorts, base lodges have restaurants. Watch the time for the descent before dark.
4. 18:00 Return to Santiago + relaxed dinner 3h

   Wind back down to the city by early evening. After a mountain day, a relaxed Chilean dinner in Lastarria or Providencia — pastel de choclo and a glass of red, or a comforting cazuela.

   Cost: CLP 15,000-30,000 ($16-32) per person TIP: Mountain days are tiring — keep dinner easy and local. Liguria in Providencia is a lively bistro for exactly this. A pisco sour or a glass of Carmenère caps the day. Cards accepted.

Meal Recommendations

Activities

1. 09:30 Museo de la Memoria y los Derechos Humanos 2h

   A powerful, free museum documenting the 1973-1990 dictatorship and its human-rights legacy — essential context for understanding modern Chile and the politics you've sensed around the city. Sobering but deeply worthwhile.

   Cost: Free TIP: Free admission; allow 1.5-2 hours. It's moving and confronting. Reachable via Quinta Normal Metro. A meaningful counterweight to the wine and mountains, and it makes the rest of the trip make more sense.
2. 12:00 Barrio Italia or Bellas Artes wander 2h

   Explore a neighborhood missed earlier — trendy Barrio Italia (design shops, patios, craft beer, cafés in old houses) or the museum-and-café district of Bellas Artes by Parque Forestal, with the Museo Nacional de Bellas Artes.

   Cost: Free (shopping/coffee extra) TIP: Barrio Italia is great for browsing independent design and antiques over coffee. Bellas Artes pairs a fine-arts museum with park strolling and Emporio La Rosa ice cream. A relaxed, local-feeling last morning.
3. 14:00 Final lunch — a completo or market seafood 1h30

   A last Chilean meal — a loaded completo at Dominó or Fuente Alemana, or a final seafood lunch at Mercado Central or La Vega. The cheap, iconic flavors to remember the trip by.

   Cost: CLP 4,500-25,000 ($5-27) per person TIP: A completo italiano is the quintessential cheap Santiago bite. Fuente Alemana's giant sandwiches are a fitting send-off. Keep it light if you've a long flight ahead. Cash plus cards.
4. 16:00 Souvenirs + airport (SCL) 2h30

   Pick up Chilean wine, pisco, lapis lazuli (Chile's blue stone), or copper crafts, then head to Arturo Merino Benítez Airport (SCL) — about 15km northwest — by official transfer van, the airport bus, or Uber/Cabify.

   Cost: Bus CLP 2,000-3,500 / transfer CLP 8,000-12,000 / Uber varies TIP: Lapis lazuli jewelry and good-value Chilean wine are characteristic gifts (declare wine within allowances). Allow extra time for SCL on long-haul departures; the official Transvip van or a pre-booked Uber is cleanest. Avoid touts inside the terminal.

Meal Recommendations