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traveling in Chile

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My husband and I would like to travel to Chile for around 3-4 weeks this Dec. sometime around the 27th 2012. We are 65 yrs. of age and like to travel on our own. We are from Colombia and we speak Spanish.

Please give us an idea of where to land from Toronto. Also which city would you recommend to start out trip and tell us about the weather in such city, We like to hike. Also if you have a couple of names for a budget -medium hotels and your favorite restaurants. Places to go and if you could possible help to prepare an itinerary.

Your comments and suggestions are very welcomed!

Muchas gracias!