Arrive in Santiago (looks like Qantas just started flying there non-stop from Sydney), check it out for a couple of days on public transportation (although some neighborhoods now have nice bike infrastructure) and then ride to Viña del Mar/Valparaiso. If you're into wines, there are many vineyards on the way to Viña, but only a few open to tourists. Look for the ones that grow the carménère variety. Follow the coast south from Viña. Remember that Chile is a narrow but very long country so if you're on a schedule you may have to fly to get to various locations to see certain cool natural attractions. If there is one place not to miss is the Carretera Austral (which is also in my plans.) This is in southern Chile. You can detour in several places end up in the Argentinean side and from there catch a flight to Buenos Aires and on to Uruguay. A friend of mine is currently riding in South America on a motorcycle. He's also into cyclotourism. After seeing half of South America he gives the highest marks to Chile for road conditions and scenery. He also speaks highly, believe it or not, about Colombia also for scenery, people and bicycle friendliness. I had heard about other cyclists having a positive experience there, too. CGOAB has a blog about this Australian/Dutch family going around the world on tandems. They seem to have liked that country very much, too.
Last edited by Chris Pringle; 04-28-12 at 02:49 PM.