Recommendations for rides out of Santiago, Chile
 

I am currently working in Palmer Station, Antarctica. My KLR will arrive in the port of San Antonio, Chile, around 1 October, 2013.

I will have a female companion as a riding partner for about three weeks. She's completely new to motorcycle travel, so our days will be short, with more of a focus on off-bike activities and walking tours when not moving place to place. We will be renting gear for her to be properly kitted out for safety and comfort.

We are currently thinking of some coastal town exploration north of Santiago, then turn east toward Maipu and wine country. If possible to comfortably cross the Andes toward Mendoza, Argentina in October, I think that would be a fun destination. We're into wine and food exploration. :scooter::palm:bier

What other high-points does the community remember from 1000km radius of Santiago?

The "Cajon del Maipo" valley east of Santiago is quite nice, should be warm enough to explore a bit higher up by October.
I would obviously do Viña and Valparaiso, take the smaller roads, you can avoid all tolls and therefore all boring motorways, a bit tricky, but worth it for the ride.
The trip over to Mendoza is pretty awesome, but make sure you pick the right weather for it, you don't want to get snowed in on a m.c. at 5000m.
The valleys further north will be great in October, there is a great trip you can do which parallels the Panamerican highway to the East and you can get several of the Valleys in, very popular with the small legion of Chilean riders, it will take you through Combarbala, Monte Patria, Ovalle, Vicuña and even up to Pisco Elqui. 150 odd kms East of Vicuña there are some pretty cool thermal baths where you can hang out in the middle of the Andes with a spectacular view of the snow capped mountains, great ride up and you won't see a soul, not many locals know about it.
Have fun, but take care of your bike, Chileans will not bat an eyelid at putting your bike on the back of a truck.