Traveling to Cuba With Points and Miles

Learn how you can explore the Caribbean island without breaking the bank.

With stunning beaches and a vibrant culture, Cuba is considered a top vacation destination for travelers all across the world. But due to tight travel restrictions that date all the way back to the 1960s, most U.S. tourists haven’t had the chance to experience all that the Caribbean island has to offer. At least until now.

For the first time in decades, in June 2016, the U.S. Department of Transportation awarded approval for six U.S. airlines to travel to Cuba’s capital city, Havana. President Obama’s visit to Cuba in early 2016 – the first by a sitting U.S. president in 88 years – has helped open up travel between the two countries. As a Canadian, I’ve already had the pleasure of visiting Cuba’s beautiful beaches and taking in their great music and culture. Check out a few tips I’ve found on covering part of the cost of your trip with loyalty points and miles.


Daily flights from Fort Lauderdale, New York, and Orlando have made JetBlue the carrier with the most routes to Cuba’s capital. If you’re considering booking a flight to Cuba with JetBlue, try charging the cost of airfare to a travel rewards credit card. A JetBlue Plus or JetBlue Business card can help you earn half off in-flight movies, cocktails and food, a free checked bag for you and up to three friends on the same reservation and 10 percent back when you redeem points you’ve accrued during the trip.

The Citi ThankYou Premier Card can also bring you big savings, including three times the points on airfare, hotels and public transportation.

But even without a travel rewards credit card, JetBlue TrueBlue members can take advantage of amazing deals on flights to and from Cuba. JetBlue’s inaugural trip to Cuba on August 31st costs $204 or just 7,000 points round trip. That’s a value of more than two cents per award mile! It’s hard to beat that kind of deal, especially when you consider that demand is sure to be sky high.

American Airlines

For those of you in Miami, American Airlines may be the go-to carrier for flights to Cuba. The U.S. Department of Transportation recently awarded American four flights between Miami and Havana each day. Since the two cities are separated by less than 350 miles, AAdvantage program members won’t have to redeem too many loyalty points to reach their final destination. Cuba is located in American Airline’s Caribbean region, meaning you’ll usually be able to find an economy seat for 15,000 miles compared to 20,000 or even 30,000 miles for flights to South America and Europe.

You can also earn an extra 5,000 miles for every 20,000 Starwood points you convert into AAdvantage miles, opening the door for even more savings.

Although it may be tempting to book your vacation right this minute (trust me, I know the feeling), you should take a few minutes to review the travel limitations that come with redeeming rewards points and miles for a flight to Cuba. For example, before boarding your flight you’ll need to sign an affidavit stating the reason for your trip. This can include anything from a family visit to an educational adventure. Just be sure to think it through before arriving at the airport.

Delta Airlines

Delta is gearing up to accommodate thousands of awards travelers with daily flights from three different airport hubs – Atlanta, Miami and New York. For around 35,000 SkyMiles, you should be able to snag a round-trip ticket with Delta. While the airline has yet to offer any special deals on flights to Cuba, that doesn’t mean you can’t rack up a few extra miles and points along the way. By signing up for the Gold Delta SkyMiles credit card, you’ll enjoy priority boarding on all flights and earn twice as many miles for every dollar you spend on airfare with Delta.

Best of all, there are no foreign transaction fees. So go ahead and order a cocktail (or two or three) once you finally make it to the beach!

For the first time in decades, U.S. tourists have the chance to experience all the sights and sounds of Cuba. Try out the tips I’ve outlined above to make sure you get to explore the Caribbean island without breaking the bank.

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