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How to get to Valparaiso and Santa Cruz from Santiago

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I am in the stages of planning a trip to Chile. I'm not sure when we are going or for how long, but I know we want to go to Santiago, Valparaiso and Santa Cruz, but I'm not sure how we should get to Valparaiso and Santa Cruz. We definitely do not want to drive ourselves.

How expensive would it be to hire a taxi or private driver?

I have read that there are buses. How easy and safe are these to take if we don't speak Spanish? We will only have one roller bag and one shoulder bag each.

To get to Santa Cruz, we wouldn't mind taking a tour from Santiago (either day trip or overnight). We plan on taking a wine/food tour once we get there anyway.

Any recommendation you have will be greatly appreciated.

Thank you, Inor

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