Santiago de Chile skyline with the Andes
May 6 — 13 · Eight days

Santiago &
Valparaíso.

Three peaks. The rest stays open.

Valparaíso · Fri–Sat Cajón del Maipo · Sun Demencia · Tue

Weekdays split: you work, I'll roam. Evenings we meet up. Three things anchor the week: a Friday–Saturday in Valparaíso, a Sunday up to the Andes, and Tuesday at Demencia.

🌤
Santiago
18–20°C
🌙
Nights
7–13°C
🌧
Valpo
Sat may be wet
🏔
Cajón
Near freezing
Three peaks
Cerro Alegre, Valparaíso
Peak one
Valparaíso
May 8–9 · the cerros
Embalse El Yeso
Peak two
Cajón del Maipo
May 10 · 2,500m
Fine dining, candlelit
Peak three
Demencia
May 12 · the closer
The week
May 6 Wednesday Arrival
2:35 AM landing No plans til evening

Landing at 2:35 AM. Sleep. Keep the first night traditional and close: dinner at Confitería Torres in Isidora.

Park at dusk, Santiago
First night, low lift
Restaurant at night
Traditional Santiago dinner
Midday · solo
Lunch: Fuente Mardoqueo Las Condes

If I'm up and functioning, this is the move: a classic Chilean sandwich lunch near the base. Order a Barros Luco and keep the rest of the day loose.

Evening · together
Dinner: Confitería Torres Isidora

Old-school Chilean staples, easier from Los Condes, and better value on a low-energy first night than doing a full polished dinner.

May 7 Thursday You work
Solo daytime Dinner together

I'll work from Café Forastero and wander Barrio Yungay. Dinner at Liguria when you're off.

Barrio Yungay, Santiago

Barrio Yungay · Santiago's oldest neighbourhood

Lunch · solo
Ciro's Bar de Isidora

Quick fuente de soda lunch near the base. Caldo de tronco or pierna de cerdo, then keep moving.

Evening · together
Dinner: Liguria

Classic Santiago bistro — pisco sours, ceviches, home by 10. Chill night before the weekend.

Cerro Alegre, Valparaíso

Cerro Alegre · where we'll be

May 8 Friday · your day off Peak one · Valpo
Bus to Valpo Golden hour Terrace dinner Live music maybe

Morning bus to Valparaíso. Afternoon to settle. Golden hour on the cerros, dinner up the hill, and a bar with live music if we're feeling it.

Cerro Alegre, Valparaíso
10–11 AM
Pullman bus to Valparaíso

~90 minutes from Terminal Alameda. Arrive early afternoon, drop bags on Cerro Alegre.

Afternoon
Lunch at Café Turri, then a pause

Classic Cerro Concepción terrace, port view, slow service — exactly right for arrival day. Then actually rest at the hotel until 5:30.

5:30 PM · golden hour
Walk Cerro Alegre → Cerro Concepción

The Friday peak. Light over the painted houses, the Pacific out to the west, funiculars running.

Dinner · 8 PM · target
Fauna — terrace over the port

Cerro Alegre's iconic terrace restaurant. Port lights coming on as we dine, drinks flowing, no rush.

11 PM · if we have the energy
Brighton or La Piedra Feliz

Brighton: live Latin music on a black-and-white tile terrace. La Piedra Feliz: salsa room, tango room, dance classes if we want to jump in. Skip if we're tired.

May 9 Saturday Valpo · slow
No alarms Neruda's house Long lunch Bus home

No alarms. Coffee with a view. One more walk, Neruda's house, a long lunch, then the bus home.

Cerro Concepción, Valparaíso
Cerro Concepción · morning
Valparaíso port view
Funicular · if we didn't ride one
Morning · slow
Coffee on the terrace, then Cerros Alegre + Concepción again

Whatever we missed yesterday, in different light.

Late morning
La Sebastiana — Neruda's house

Short Uber to Cerro Florida. Five-story clutter and the best view in the city from the top floor. 45 minutes inside, then back. Optional.

1:30 PM · lunch
La Concepción — unhurried, on the cerro

Ranked #4 in Valparaíso, World's 50 Best listed. Terrace with port view, relaxed kitchen, two hours minimum. The best possible last meal in Valpo before the bus.

~4 PM
Bus back to Santiago

Home by 6. Empanadas in, wine, bed early. Sunday needs energy.

Embalse El Yeso — turquoise glacial lake

Embalse el Yeso · Cajón del Maipo · 2,500m

May 10 Sunday Peak two · Andes
Private driver 2,500m altitude Glacial lake Picnic

Up to Embalse el Yeso, the glacial lake in the Cajón. A driver for the day. 10 AM start, home for dinner.

Cajón del Maipo
10 AM
Driver picks us up

No early alarm. The road closes for winter by late May — this is the last window.

Midday
Up to 2,500m — Embalse el Yeso

Turquoise glacial reservoir ringed by snow peaks. Autumn color on the drive up.

~1:30 PM
Picnic at the lake

I'll pack it. Bread, cheese, fruit, thermos. Thin air, cold wind, quiet.

Afternoon
Baños Morales on the way down — optional

Thermal pools. Warmth after the altitude.

Evening
Home by 6–7. Order in, done.

You earned horizontal time. You have work tomorrow.

May 11 Monday You work
Museum solo Old-school lunch

Light solo day for me. Museum, then a real old-Santiago lunch.

Museo Chileno de Arte Precolombino, Santiago
Arte Precolombino
Historic Santiago restaurant evening
Ana María · Monday lunch
My day
Museo Chileno de Arte Precolombino

One of the best museums in South America. Then wander.

Lunch · solo
Ana María

The museum-day lunch. Caldillo de congrio, plateada, or the most traditional daily special on the board.

May 12 Tuesday Peak three · Demencia
Classic lunch solo Best dinner Walk home slow

Solo lunch first, then the night is Demencia — the one real splurge.

Lunch · solo
El Hoyo

Beloved, loud, and classic. Lengua con puré if you're in, pernil or cazuela if you want the safer lunch version.

Dinner · Tuesday · target
Demencia

Benjamín Nast's place. Playful, creative Chilean ingredients. The best meal of the trip.

After
Walk home the long way

Cold May night, quiet streets.

May 13 Wednesday Out
Slow morning 10:55 PM departure

Morning coffee optional. Last day in Los Condes, then the airport for a late-night flight.

Morning
Black Mamba or wherever's close

Short goodbye.

10:55 PM · flight
LATAM LA 6060 to JFK

Departs Santiago on Wednesday, May 13, 2026 at 10:55 PM and arrives at JFK on Thursday, May 14 at 9:00 AM.

Reference

Booking status

Tap a status to cycle it. Saved only in this browser.

Flights

Outbound is LATAM LA 6060 on Wednesday, May 13 at 10:55 PM, arriving JFK Thursday, May 14 at 9:00 AM.

Santiago base

Staying at La Gloria in Los Condes.

Valpo stay

Hotel Boutique 17 is still the planned stay, but the live docs needed a status pass.

Fauna

Target slot is Friday, May 8 at 8 PM.

Demencia

Target slot is Tuesday, May 12 at 8 PM.

Cajón driver

Still needs a clear yes/no status for Sunday, May 10.

Liguria

Thursday dinner if you want a reservation instead of walking in.

Valpo buses

Still shown as flexible, but worth locking if you want exact timing.

Friday nightlife

Brighton or La Piedra Feliz only if the night still has legs.

Meals in order
Wed · arrival
Confitería Torres Isidora

Traditional first night, close to Los Condes

Thu · Santiago
Liguria

Classic bistro, pisco sours

Fri · Valpo lunch
Café Turri

Cerro Concepción terrace, port view

Fri · Valpo dinner
Fauna

Terrace over the port, lights at dusk

Sat · last Valpo meal
La Concepción

Long lunch on the cerro

Mon · lunch
Ana María

Old-school Santiago lunch, classics first

Tue · the closer
Demencia

Benjamín Nast · best of the trip

Practical
Base
La Gloria · Los Condes
Santiago home base for the week
Weather
Cool week, cold nights
Valpo looks cooler; Saturday may bring rain
Valpo bus
Pullman — Terminal Alameda
~90 min each way
Cash
Markets only
Card everywhere else
Valpo nightlife
Brighton · La Piedra Feliz
Both 2 min from Hotel Boutique 17
Departure
Wed May 13 · 10:55 PM
LATAM LA 6060 to JFK

This version keeps the public site high-level: status lives here, while confirmation numbers, exact addresses, and driver details stay off-page.