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How to Travel to Cuba Legally from the U.S.


It’s 5:00 a.m. at Miami International Airport as I file into Sun Country’s check-in line for my charter flight to Havana. Through my bleary, sleep-deprived eyes, I notice something striking. While I’m pulling a small roller-board suitcase, most other passengers are pushing large carts stacked high with shrink-wrapped plasma TVs, bicycles, and ottoman–sized wads of clothing. Their reasons for traveling to Cuba are different than mine: They come to see and assist family, and I to quell a curiosity that’s been building collectively in the U.S. since the trade embargo went into effect in 1960.

Yes, for U.S. citizens, legal travel to Cuba is now possible. However, you’ll face its complexities before you ever touch down in Havana. And while the rules continue to evolve as president Obama eases restrictions, here’s the latest on what you need to know for planning a trip (at least for the moment).

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