Hi there

I am not Chilean but I have been living in Chile for 5 years so I am going to give you a few tips.

For me the great surprise when I moved to Chile was that I was told not to put up my tent to sleep when I traveled. The reason was that you might get robbed or worse during night. In Chile you should suspect anything from anyone.

So I don´t know how you are going to travel but when I travel by motorcycle in Chile now I do things like drive far off into the desert until I cannot see or hear the highway anymore and there I make my tent for the night. Because if I can be seen from the highway or from local houses then I have no place safe to sleep.

The second thing I want to advice you about is to take care of your girlfriend. She runs a serious risk of getting assaulted if she walks alone after dark. Unshamed stares at close distance, shoutings and whistling she will just have to live with. For some strange reason Chilean men are crazy about white women. Why I do not know as white women deviate from their own race.

Now for your map. You have marked off Valparaiso. My suggestion would be to take extra care there because Valparaiso has very ugly crime where you can get physically hurt if you walk out in the streets at night as foreigners. I would suggest don´t walk out at night in the streets there. Viña del Mar is safer. You could sleep there and just visit Valparaiso at day.

I see you plan to travel south in Chile also. I take it you will pass through Temuco also then. In that case I can suggest a place to rent a cabin for some days and in the same time learn to tame horses.
Domaracional.cl

And here just in case you would like to print out road maps of Chile.
Mapas Ruteros de Chile

Good luck!