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.
Landing at 2:35 AM. Sleep. Meet up for dinner at Mestizo.
Park setting, good food, easy first night. No rush.
I'll work from Café Forastero and wander Barrio Yungay. Dinner at Liguria when you're off.
Barrio Yungay · Santiago's oldest neighbourhood
Classic Santiago bistro — pisco sours, ceviches, home by 10. Chill night before the weekend.
Cerro Alegre · where we'll be
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~90 minutes from Terminal Alameda. Arrive early afternoon, drop bags on Cerro Alegre.
Classic Cerro Concepción terrace, port view, slow service — exactly right for arrival day. Then actually rest at the hotel until 5:30.
The Friday peak. Light over the painted houses, the Pacific out to the west, funiculars running.
Cerro Alegre boutique hotel's restaurant. The terrace is the whole point — port lights coming on as we dine.
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.
No alarms. Coffee with a view. One more walk, Neruda's house, a long lunch, then the bus home.
Whatever we missed yesterday, in different light.
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.
Good terrace, relaxed kitchen, two hours minimum. The last meal in Valpo before the bus.
Home by 6. Empanadas in, wine, bed early. Sunday needs energy.
Embalse el Yeso · Cajón del Maipo · 2,500m
Up to Embalse el Yeso, the glacial lake in the Cajón. A driver for the day. 10 AM start, home for dinner.
Cajón del MaipoNo early alarm. The road closes for winter by late May — this is the last window.
Turquoise glacial reservoir ringed by snow peaks. Autumn color on the drive up.
I'll pack it. Bread, cheese, fruit, thermos. Thin air, cold wind, quiet.
Thermal pools. Warmth after the altitude.
You earned horizontal time. You have work tomorrow.
Light solo day for me. Chill dinner together.
One of the best museums in South America. Then wander.
Wine bar in Lastarria — 250 Chilean wines, small plates, old restored house. The right pace for a Monday.
Daytime solo. The night is Demencia — the nicest dinner.
Sprawling flea market, antiques, food stalls.
Benjamín Nast's place. Playful, creative Chilean ingredients. The best meal of the trip.
Cold May night, quiet streets.
Morning coffee optional. Afternoon flight.
Short goodbye.
Park setting, easy first night
Classic bistro, pisco sours
Cerro Concepción terrace, port view
Terrace over the port, lights at dusk
Long lunch on the cerro
250 Chilean wines, Lastarria
Benjamín Nast · best of the trip
I'll handle bookings — the Valpo stay, Fauna, Demencia, Sunday's driver. Tell me if you want to swap anything.