Santiago &
Valparaíso.

Av. Presidente Kennedy 5413, open until 9–10 PM. Falabella first: adapter (ask for "adaptador universal" — Chile uses Type C/L) + umbrella. Then Jumbo: mote con huesillos (refrigerated drinks), Calaf cookies, Ambrosoli candies, manjar, deodorant.

Av. Nueva Costanera 4076, Vitacura — 15 min Uber. Covered terraza with blue lighting. Gaston Acurio's cevichería, #26 Latin America's 50 Best. She loves seafood — this is the right first dinner. Pisco sour, cebiche clásico, tiradito, grilled octopus. Reservation confirmed: 8:30 PM, Terraza.

Get it done properly before going out. Target done by 1 PM. No guilt about being inside — the afternoon has plenty.

Av. Matta 871, Barrio Yungay. The classic fuente de soda — Barros Luco on marraqueta, fluorescent lights, no tourists. One of Santiago's most old-school lunch counters. Pulling this forward from Tuesday clears that day up before Demencia.

Av. Presidente Kennedy 5413 — one stop covers most of the buyable checklist. Refrigerated drinks: mote con huesillos carton. Snack aisle: Super 8, Ramitas, Tritón. Refrigerated desserts: Manjarate. Baked goods: alfajores with manjar (Calaf). Candy: Ambrosoli. Pack the Valpo snacks separately — Super 8, Ramitas, and Tritón travel fine in a bag. Back home by 4 PM, pack for Valpo, rest.

Head toward Alameda. Closes at 9 PM so be seated by 8 at the latest — leave time for the walk.

Alameda 1570. Santiago's oldest restaurant, Est. 1879 — dark wood, white tablecloths, waiters who've been there forever. Order light so there's room for street food after. Order for her on arrival: borgoña (ask the waiter — red wine with strawberries, she needs no context). To start: locos mayo (abalone with mayo, very Chilean). Main: costillar asado (slow-roasted ribs) — share one between you. That's the right amount.

Av. Libertador General Bernardo O'Higgins 676 — 5 min walk east from Torres on the same street. "One more thing you have to try." Share one completo italiano — avocado, tomato, mayo, the works. Standing up, after the oldest restaurant in the city. The contrast is the point. Order: one completo italiano to share, ask for extra pebre if they have it.

Start slow — coffee with a view from the hotel terrace. Then ride Ascensor Concepción ($100, 7:00–21:30) up to Cerro Concepción. Walk immediately to Paseo Gervasoni — the classic panoramic terrace right at the top, sweeping port view, one of the best lookout points in the city. Take it in, then start walking toward Bellavista. On the way, keep an eye on Pasaje Gálvez at Templeman — there's a small plaza with a slide embedded next to a staircase, a Valpo quirk, worth doing once.

Different cerro from Friday's Alegre/Concepción walk. Bellavista is the most famous street art hill in Valpo — massive three-story murals, quieter than the tourist cerros, genuinely impressive. 20–30 min walk from Cerro Concepción. Completely different register from Friday's golden hour walk.

Walk down to the lower city. Plaza Sotomayor first — the Navy HQ blue palace and War of the Pacific monument are right there, 10 min to take it in, genuinely striking. Then cut to Mercado El Cardonal (Av. Argentina 80) — working market with counter spots doing empanadas de pino and mariscos for ~$2–3 USD. Knock out the taste checklist empanada here: order an empanada de pino, get a seafood one if they have it. Raw port energy, nothing touristy about it. Then ride Ascensor El Peral back up — runs 7:00–21:30, costs $100, lands you directly at Paseo Yugoslavo on Cerro Alegre, a 2-min walk from La Concepción. Three funiculars across two days, all different.

El Peral drops you at Paseo Yugoslavo — Palacio Baburizza is right there on the left, the pale yellow art nouveau mansion that houses the fine arts museum. Worth 2 minutes to look at the exterior even if you don't go in, it's one of the most beautiful buildings in Valpo. Then 2 min walk to La Concepción: ranked #4 in Valparaíso, World's 50 Best listed. Terrace with port view, relaxed kitchen, two hours minimum. Order the caldillo de congrio if it's on the menu — Neruda's dish, correct place to have it. The best possible last meal in Valpo before the bus.

Don't rush lunch — but be out by 3:30. Walk down the cerro at a comfortable pace, call an Uber from the lower city. Terminal de Buses Valparaíso is 20–25 min away. Be there by 4:45 PM for the 5:15 bus — that's your hard deadline.

Locked back to Terminal Pajaritos. ~90 min ride, home by 7:15 PM. Time to decompress and get ready before Chipe Libre.

Barrio Bellavista — República del Pisco concept, pisco cocktails from Chile and Peru, good food, Saturday night energy. Emily doesn't need a wine program — she needs great cocktails and a fun room after a beautiful Valpo weekend. This is the right call. Book ahead.

Santiago's historic iron market hall — built in 1872, one of the most beautiful market structures in South America. Raw, chaotic, extraordinary at this hour before the tourist lunch crowd arrives. Seafood stalls, produce, the smell of the place. Solo, backpack optional, 45 min. On the way north toward the cemetery.

One of the most extraordinary cemeteries in the world — vast marble cities of the dead, Neruda and Allende buried here, overwhelming sense of scale. Opens at 8 AM, free entry. One hour minimum. Nothing else in Santiago hits quite like this on a solo morning.

Bandera 361 — one of the best pre-Columbian collections in South America. Textiles, ceramics, gold work across civilisations from the Andes to Mesoamerica. 1.5–2 hours. Best museum in Santiago, no contest.

The correct museum-day lunch. Caldillo de congrio, plateada, or whatever the daily special is on the board. Old-school, no tourists, exactly right after a heavy morning.

No agenda. You've had a full morning — walk, stop somewhere for a coffee, let the afternoon be unstructured before the evening.

The legendary Chilean sandwich spot. Share a chacarero and a Barros Luco on marraqueta. No reservation needed, no ceremony — the perfect low-key night between Sunday's full city day and Demencia tomorrow. Open until 9:30 PM.

The city's main produce market — raw, chaotic, extraordinary. Breakfast from one of the stalls inside: cazuela, empanadas, fresh juice. Get sopaipillas if a vendor has them hot — fried pumpkin dough with pebre, the quintessential Chilean street-food moment, and La Vega is where it happens correctly. Backpack is completely fine here. One of the most alive things Santiago does and most visitors never see it.

Last slow walk in the city. No agenda — coffee, a bookshop, sit somewhere and watch the street. Let it wind down naturally.

Somewhere with reliable WiFi and low noise. Café Forastero if you're in Yungay, or any Lastarria café you've already been to and know works. Order something, settle in early, be ready by 2.

Done.

Santiago's best antique and design street. Interesting shops, good cafés, nothing urgent. A clean final neighbourhood to end on — visually different from everything else on the trip.

No reservation, no plan. Sandwich, a café con leche, something simple. Let the city finish on its own terms.

~45 min from central Santiago, potentially longer in evening traffic. Aim to be at the airport by 7:30–8:00 PM for a 10:55 PM international departure — LATAM wants 2.5–3 hours for international check-in.

Departs Santiago Wednesday May 13 at 10:55 PM. Arrives JFK Thursday May 14 at 9:00 AM.