Going on a Patagonia cruise in December and will layover on the way too and from in Santiago.

On the way back I'm looking like I'll have a day or so in Santiago.
I don't mind just booking at room at the airport Holiday Inn, but I think I'd prefer to get out into the city.
Anything worth seeing or doing for a day or two? Departing flight doesn't leave until after 10PM.

Also if anyone has a hotel recommendation in Punta Arenas for two nights. My Latam flight from Santiago to PUnta Arenas arrives very late so I've padded an extra day into my itinerary on the way down just in case there are any hiccups

Sounds like a great trip!

I'd prefer to stay in Santiago and just confirm/pay for a late checkout with the hotel vs staying near the airport to be closer to everything but either option works. A lot of the flights to the states depart late in the evening so this is common down there. My favorites are the Mandarin Oriental and the Singular Santiago.

Happy to help if you're looking for recommendations!

Punta Arenas Hotel Recs:
- La Yegua Loca
- Hotel Almasur
- Hotel Jose Nogueira

In Punta Arenas, hotel Cabo de Hornos on the square is about as good as it gets. And definitely hit the Shackleton Bar (also on the square).

In Santiago, the Ritz Carlton and W Santiago both have great rooftop bars and are in a nice walking neighborhood with lots of great restaurants.

Santiago has 5 wine valleys. I try to do one every time I go. You might be able to combine a trip to the Casablanca region and then carry on to Valiparasio. It is a nice port city.
Or you stay in the city, go to the market which has fabulous seafood. Santiago also has a decent subway system as well.

Don't have a recommendation for a hotel in Punta Arenas but can recommend you stop at whatever place is available and order a few "Completos." They're all over Chile and they're really good.

Jealous always wanted to visit Chile.

Love Santiago. Visit Boca y Nariz wine bar. Great spot.

They are a bunch of hyper green ESG socialists and routinely protest in front of the US Embassy in Santiago…but other than that they are friendly and it is a great country.

I've rarely visit a place and have zero desire to go back. I have zero desire to go back to Santiago. I'm sure you can find something to entertain you for a day or two, but that was the most boring city I've been to in Latin America.

Concha Y Toro Winery!

The devil lives in the cellar there!