Part the Second: Getting to Cuba

Because it’s so difficult for an American company to do business with Cuba, it can be quite an ordeal to find a flight from the U.S. If you’ve got all your Treasury ducks in a row, though, it is possible.

Believe it or not, there are plenty of run-of-the-mill, passenger flights out of Miami. From what I’ve been able to gather, most of them are filled with Cuban-Americans visiting their families. They can only get a visa for 21 days total in a year, though, and flights around Christmas are usually full. If you’re thinking about going to Cuba when it’s all chilly and cold up north – what better time? – then you better plan ahead and buy your tickets in September.

Gulfstream Air, Tico Travel, and Marazul Charters are some likely candidates to get you started. We used Tico Travel on our first trip and while they got us there and back, we had some hitches that made the trip more worrisome that it needed to be (although they made right with everything in the end.) Gulfstream is a company owned by Continental Airlines and we used them on our second trip. If things go well, expect to pay roughly $350 round trip from Miami to Havana. If plans blow up in you face, you can still get there for $9014!

Let me explain.

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