My Spanish is serviceable, but not fluent by any stretch. That said, I've never had any issues in S.A. I've been to Chile 5 times in the past 10 years and I can't wait to go back soon. Generally, everyone I've met in Chile has been super nice. I spent two days for work about 10 years ago at a copper mining camp about 400km NE of Santiago up in the Andes and although none of those workers spoke so much as a single word of English, they were incredibly welcoming and just wanted to share grilled meat and cheap wine. It was awesome. Valpo is a really unique and cool city (albeit an exhausting place to walk around) and Santiago is just a really nice big city. It's one of the cleanest big cities I've been to (Buenos Aires, while awesome, is one of the dirtiest). And as tiger mentions, there are a ton of really accessible wine regions that are starting to put out some really good wines. One of the owners of our local wine shop is from Santiago and he hooked us up on our last visit with some visits to some otherwise private wineries and it was incredible.