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US to Costa Rica

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My question comes in a couple of parts.

1) Has anyone recently had any trouble with the 90-days policy on US citizens entering Costa Rica? I will be there for slightly over 90 days, but will leave via bus (not plane) within that time to visit Panama through a school-related trip. The programs keeps telling me that they've had no problems with the policy, but I'd like to double check.

2) It's been a while since I've traveled out of the country. If I have a stop on my way out, how much time should I make sure I have during my layover? Will I have to deal with any customs-sort of activity during my layover?

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