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Itinerary help in Chile

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My sister and I are going to Argentina (primarily Buenos Aires) and Chile in late February and early March for my sister's 60th birthday. We have just over 2 weeks in total. Our plan is to spend approximately 7 days in Chile.

Based on our early research we are thinking of spending about 3-4 days in Santiago (presuming one day trip from there) and then a couple of nights in Valparaiso. Where else would any of you suggest in central Chile that would be worth a day trip or a couple nights outside of these two locations?

My current thoughts (with admittedly not enough research) would be either to spend time south of Santiago (winery tours,etc.) or north of Valpo. Is La Serena worth a visit? Is the Elqui Valley worth a night or two to enjoy the scenery and perhaps a visit to an observatory (keeping in mind that my sister has a bad knee and can't do much in the way of hiking)? Is it worth going to Isla Damas to see the Humboldt penguins etc.?

Any ideas are welcome!

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