You will be able to get by. English is not widely spoken in Chile, but people will try to understand you and help.
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it not rare to find someone speaking in English in Viña del Mar
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Let me put it like this... Been there 3 times, my Spanish is at a 3 year old kid's level and I didn't have any real problems. As a rule I can say one word sentences, with an occasional two word. There are enough people who speak enough English to make it fairly easy to do most anything you want. The worse case I had, was wanting to return to a particular restaurant I had visited before. The cab driver understood I wanted to eat but couldn't understand my directions... so he simply pulled the cab over, told me to "wait" and asked several people on sidewalk who spoke 'English'. By the third person he had a translator for us, only to discover the restaurant had closed. My biggest suggestion is to carry your hotel's name, address & phone number with you. Think of it as a "If lost return to". Have fun.
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You can but you always get more out of travelling it you take a lanmguage course beforehand. www.cactuslanguage.com do language courses in Santiago de and Pucon as well as other places in S America. I took one of their courses in Costa Rica and it was great!
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If you need a guide just go to www.chiletours.freetzi.com
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