Using rewards miles to fly to Cuba

Dear Cashing In,
My wife and I have some points in a few different reward programs. What is the best way to use those points to fly to Cuba? – Richard

Dear Richard,
One of the biggest travel stories in the past year, especially for those who are into adventurous destinations, is the opening up of Cuba. Although the small island nation is just 90 miles south of Key West, Florida, it might as well have been halfway around the world for U.S. travelers.

For decades, the U.S. government’s Cold War era restrictions on Cuba made it difficult to gain approval to travel there, and there were no regularly scheduled commercial flights. Americans had to provide a worthwhile reason to visit (with documentation) and either take a charter flight or travel through another country to get there.

In 2016, the trip became easier when the Obama administration eased some of the travel restrictions and began allowing U.S. airlines to fly to Cuba. There are still travel hassles: You can’t go there merely for tourism, credit cards don’t work, Internet access is shaky and the country lacks many modern conveniences. See the U.S. State Department’s travel advisories for Cuba for details.

But the widespread availability of flights makes travel to Cuba a possibility in a way that has not existed in most of our lifetimes. And for those who travel a lot or have a travel rewards credit card, the good news is that there seem to be plenty of award seats available.

Rewards options
It is tough to answer your question directly, without knowing how many points you have in what programs. But a quick check of those airlines that are flying to Cuba show that there are a lot of award options.

For instance, American has flights to Havana most days in the winter and spring from many cities connecting through Miami or Charlotte for 15,000 American miles each way. Citi and Barclaycard both offer credit cards with big sign-up bonuses, which would give you enough miles to get to Cuba and back.

Southwest is economical miles-wise, too. For instance, to get to Havana from Oakland, you have to change planes in Denver and Fort Lauderdale, but it can be done for about 12,000 miles each way. If you live in Florida, it’s an even better deal: about 2,000 miles each way (though the trip is priced as low as $59). Chase offers Southwest cards with sign-up bonuses, and you can also transfer Chase Ultimate Rewards to Southwest.

Those two seemed to have the most award availability to Cuba with the fewest number of miles, but that could change, depending on where you live and when you are traveling.

With most of the airlines, you can book online, although you have to fill out some extra forms. For example, you need to state a valid purpose for traveling there. Some of the more commonly approved reasons are participating in educational or religious activities, visiting family and conducting journalism or professional research.

Feliz viaje mi amigos!

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