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two passports

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I have citizenship in and passports from the U.S. and Canada. My question involves traveling on one passport or the other. I plan to go to Costa Rica on my U.S. passport but I may want to go to Cuba, for which I will need my Canadian passport. Will this cause problems going from one country to the other? What disadvantages and advantages might I have with two passports and how could I best use this? Thank you.

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