Hi. We have 14 days in Chile. I was looking at existing posts and working with ChatGPT and came up with this itinerary. I know I am skipping Calama and Punta Arenas are, however, we were in similar area in Argentina (Salta, etc.) So that we don't too many flights we decided to cut it out.

Please let me know if this seems right. What we can change, etc.
FYI we are not serious hikers - beginners level is perfect for us.

Day 1 (Dec 8): Arrival in Santiago
* Arrive in Santiago, transfer to hotel.
* Light city walk: Plaza de Armas, Cerro Santa Lucía.
* Evening in Lastarria neighborhood.

Day 2 (Dec 9): Santiago
* Full day in Santiago:
* Morning: Mercado Central & Bellavista.
* Afternoon: Cerro San Cristóbal or Museum of Memory.
* Dinner with a view (Sky Costanera tower).
* Overnight in Santiago.

Day 3 (Dec 10): Valparaíso & Viña del Mar (Day Trip)
* Drive 1.5 hrs to Valparaíso.
* Explore hills, street art, funiculars.
* Afternoon stop in Viña del Mar.
* Return to Santiago for overnight.

Day 4 (Dec 11): Santiago → Punta Arenas → Puerto Natales
* Direct flight Santiago → Punta Arenas (~4 hrs).
* Scenic 3-hr drive to Puerto Natales.
* Evening at leisure along the fjord.

Day 5–8 (Dec 12–15): Torres del Paine National Park
* 4 full days for hikes & sightseeing:
* Easy: Salto Grande, Lago Nordenskjöld.
* Excursion: Boat trip to Grey Glacier.
* Base mostly in Puerto Natales (or split 1–2 nights inside the park).

Day 9 (Dec 16): Puerto Natales → Punta Arenas
* Drive back to Punta Arenas.
* Penguin tour (Isla Magdalena).
* Overnight in Punta Arenas.

Day 10 (Dec 17): Punta Arenas → Puerto Montt → Puerto Varas
* Direct flight Punta Arenas → Puerto Montt (3 hrs).
* Short 30-min drive to Puerto Varas.
* Lakeside stroll at sunset.

Day 11–13 (Dec 18–20): Lake District
* Explore Osorno Volcano, Lago Todos los Santos, Petrohué Falls.
* Day trip to Chiloé Island (Castro’s stilt houses, UNESCO churches).
* Optional kayaking, hiking, or just relaxing by the lake.

Day 14 (Dec 21): Puerto Varas → Santiago
* Direct flight back to Santiago.
* Wine tasting in Maipo Valley, Cajón del Maipo (mountain gorge), or more city time.

Day 15 (Dec 22): Departure
* Fly home from Santiago.

Thank you

Three observations:

1. I would check out the currents situation in Valparaiso. Much as we loved our time there, there were some very serious fires in 2024 and I ma not sure how well it has recovered.
2. Santiago is our least favourite city in South America. I would only spend as much time as is absolutely necessary there.
3. We did look at a trip down to Patagonia last year but decided against it as the travel logistics were quite punishing. another factor was that I was unable to hike as much as I would have liked due to an injury, so that limited activities in TdeP. I did look at staying in Puerto Natales but that seemed to involve a trip of two hours each way which was too much. I am looking again for late 2026 but feel we would need a month so as to spread out the travelling.

AI is great for designing itineraries but experience has shown me that you do need to interogate it quite closely, especially around issues of time spent in transit ..

That's a great plan for 14 days - you're able to get the best of Chile without packing it all in. I'd consider cutting a day from Santiago and spending it inside Torres del Paine, you will want to wake up to those mountains! I think you will be fine if you're going to hike as long as you decide to take trails like Salto Grande, or Grey Glacier boat tour, those are great beginner to intermediate options for hiking.
If you want to learn more about what it's like to actually complete the W Trek (in case you don't complete it) this Explorer's Passage guide summarizes the challenges of each section in a real sense.

Other than that, this looks awesome - a nice and easy flow, no unnecessary flights, with nice pacing.

I just came to this forum as a new user and found your question. We travelled through all of Chile about 8 times, everytime for 5 weeks, so I think I can help a bit:
Valparaiso: we fled after 1 or 2 hours, because all the city was to run down and so dirty, also we got warnings about a lot of crime.
Day 4: I would not call the drive from PA to PN "scenic". It is a drive through agcricultural land.
And I'd suggest staying all your days inside TdP. By staying in PN you'd waste every day about 2 hours oneway by driving in and out.
Day 9: have a plan B, because so often the afternoon tour to the Penguins are cancelled becaus of strong winds.
Day 11-13: a daytrip from Puerto Varas to Chiloe Island would be a very long and strengeous day. The drive to Castro is about 4 hours, oneway. And you have to take the ferry, therefore you also have to count the waiting time.
BTW: as domestic flights are prone for beeing late or even cancelled you always need a Plan B.

Did you hear about the terrible news on O-trek?
Because I am not allowed to post a link, you'd look at the Newspaper "BioBio.Chile.de"