The world is huge

Don't miss any of it

Travel news, itineraries, and inspiration delivered straight to your inbox.

By proceeding, you agree to our Privacy Policy and Terms of Use.


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).

Don't Miss a Trip, Tip, or Deal!

Let us do the legwork! Sign up for our free newsletter now.

By proceeding, you agree to our Privacy Policy and Terms of Use.

We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.

Top Fares From