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driving from California to Costa Rica

I am planning on driving from California to Costa Rica to bring a car down to a friend who is a Costa Rican citizen. What should I know? How safe is this? What can I do ahead of time to make this as hassle free as possible. I am familiar with Costa Rica as I lived there for a while but am not too familiar with Mexico, Nicaragua etc. I'm thinking the safest and most scenic rout is the PanAm. I am fluent in spanish but am obviously American. Is this likely to be a problem in any country?

i was also thinking that there may be a company that caravans Gringos through this area. Any ideas? I'd rather not go with a company but will consider it if I feel safety is going to be an issue.

Any information and tips would be greatly appreciated.

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