We were cycle touring in Chile back in 2012, so this write up is a bit out dated, but it will still give you a good idea what to expect.
Google map is pretty good though don’t take it for granted. OpenStreetMap is lacking but is getting better. Paper maps don’t agree with each others. Some are up to date, other has random details. So pack a few and ask around.
From what we have seen the tarmac roads are good with a wide hard packed gravel shoulder. The “el ripio” are generally good, though can be in places rather nasty to cycle on.
Oh be prepared for the dust and lot off.
Compared to the Argentinians the Chileans are much more friendlier drivers. They will slow down on the ripio when passing, will pass with much more space and even give way at pedstrian crossings. If they should toot their horns it is a friendly hello beep.
Like Argentina Chile suffers from the “not my department, not my job and can’t be asked” attitude when coming to the part of giving you information about your onwards travels. Especially when they have the “official” hat on for their company or town. Don’t even think about asking what is going on in Argentina and how to get there from Chile, they will not give you any information. The tourist information offices, campsite or hotels we have tried to contact via email are rarely answering these email. Though when you get an email you get good information. But be prepared to get random info, from what you have heard form other travellers, tourist information or even the company that is doing the services your are inquiring about.
Ask someone “is there a bus from A to B? The reply will be “yes” and that is it, until you ask for more. The service is not like the I-sites in New Zealand, where the answer would be something like – “yes there is but I think they have stopped for the season, so you have to either go via C or D, let me call for you”
Though that said, when you meet a Chilean without any hat on, they will go out of their way to help you. With information, drive hundreds of kilometres out of their way to help you or put you up for the night with full board without any question or demands regarding payment.
One thing we learnt here was to ask, ask and ask again and when when you get 4-5 answers that are the same you go with that answer, though with a grain of salt.
Going into Chile you will be checked for contaminated goods, such as dairy, meat and fresh fruits. Which makes planning ahead a few days while touring a bit hard, when you want fresh veggies with you, know that there aren’t any shops for miles and you have to cross the border.
So make sure that you have none with you as you pass the border, and do remember to tick the box on the form saying that you are carrying “contaminated” food, because if you should have forgotten some garlic, like we did, they can’t give you a massive fine. Though we have crossed twice in to Chile now and only ones had a full pannier search.
We have heard up to three hours and more wait at the crossings, when they really check over a bus and every bag they can find.
You will get a few forms to fill in and they will check and stamp your passport, again do learn your passport number because you will get to used, not only at the border crossings. And don’t lose the paperwork they give you, you will needed it as you cross the next border.