My two girlfriends (early thirties) and I want to explore Chile and Argentina soon. Is there a best time to go? Fun cities with adventure? Most beautiful, relaxing place? Best sites to find most affordable tickets both to these places and within South America? Any other tips on what to see/do would be much appreciated!!! We would likely have about 2 weeks of travel time. Thanks!
If your looking for authentic experiences you should reach out to a startup called LocalAventura based in both Argentina and Chile. They can set you up with tours from local experts like winemakers, international photojournalists, mountaineers etc. Right now their company is still growing a lot so a lot of their tour guides aren't yet listed on their website but since they are so small they really care about helping people out individually. You can set up a time to speak with the co-founder and they will plan a customized trip just for whatever your needs are. It's worth reaching out. Try emailing firstname.lastname@example.org, it's worth it believe me.
There is a lot to see in both countries and there is a lot of information about them online, but the best advice I can give you about travelling in Argentina is to bring Dollars (cash) since its value in the blue market (in the streets) is much higher than the official rate and it can save you a lot of money. It's rather safe to change on the streets (in the major cities you will hear people calling "cambio" and you can change there) and in some cities you can change in restaurants/kiosks and even hostels. Yet the southern you go the lower the rate is so if you're planning on going to the south cahnge enough cash in Buenos Aires or whereever you go from...
It depends what you like to do but I'll never forget seeing the Torres del Paine National Park. It was absolutely one of the most beautiful places I've ever seen.