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Chile itinerary for August for English only speakers

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I am planning to be in Chile in August for about 2 weeks with my husband. I would like to do Easter Island for 4 or 5 days, the San Pedro de Atacama area, Santiago, Valparaiso and some wine country exploration. What is the drive from Valparaiso to the Colchagua Valley Wine area like? We like to rent a car when possible and use local guides. Where would this work for us and when would it be better to do local tours? Can anyone recommend local guides for these areas? How difficult is it if we don't speak Spanish? Finally, what kind of weather can we expect? Any responses to my many questions would be helpful. Thanks

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