What Is It Like To Fly Southwest Airlines to Havana


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See what one of our readers thought about a recent visit to Cuba on Southwest Airlines. Below is their review:

At the Fort Lauderdale airport, it all seems a little backwards. The special ticket counter for flights to Cuba are downstairs – across from baggage claim.

When it comes to redeeming Rapid Rewards points, point redemptions are low – good value from Tampa and Fort Lauderdale however the taxes came to $47, In addition, you’ll need to buy a visa for $50 (using your credit card – this might be the last time your credit card is useful on your trip to Havana.)

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But before you check in with the Southwest Airlines agents, you need to visit a booth next to a baggage belt to buy the $50 single entry visa.

The process is easy, but strict. You are cautioned that you are not allowed to cross off anything you have written on the visa or it invalidates the visa. The agents selling the visa encourage you to take a picture of the sample visa, and then to take your time while filling it out. The questions on the visa are simple, but that part of the process is nerve wracking.

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With your visa in hand, you can proceed to the Southwest Airlines check in area. The first question the Southwest agent asked is do you have a visa? After showing them the blank visa, the Southwest agent showed me a laminated card with 12 official reasons a U.S. citizens are authorized to Cuba:

  • (1) family visits;
  • (2) official business of the U.S. government, foreign governments, and certain intergovernmental organizations;
  • (3) journalistic activity;
  • (4) professional research and professional meetings;
  • (5) educational activities;
  • (6) religious activities;
  • (7) public performances, clinics, workshops, athletic and other competitions, and exhibitions;
  • (8) support for the Cuban people;
  • (9) humanitarian projects;
  • (10) activities of private foundations or research or educational institutes;
  • (11) exportation, importation, or transmission of information or information materials;
  • (12) certain export transactions that may be considered for authorization under existing regulations and guideline

I chose number (5): educational activities. It was noted in my reservation, and then after swiping my passport, I was all checked in. They also gave me a card with basic information about Cuba along with a customs form, and a health declaration to fill out.

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Flights are short, but service is provided. And if you purchase Southwests on-board wifi ($8) or the texting package ($2) the service even works on the ground in Cuba.

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I sat towards the back of the aircraft on the short flight, and I saw another uniformed employee that was not part of the cabin crew. He was a Southwest Mechanic who explained that his assignment was to ride along just in case something maintenance related is discovered while the plane is on the ground in Havana.

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Upon arrival … money and the internet

Have you traveled to Cuba yet? Feel free to share your thoughts below! 

Editorial Note: Opinions, analyses, reviews or suggestions expressed on this site are those of the author’s alone, and have not been reviewed, approved or otherwise endorsed by any card issuer.

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Here at Points, Miles and Martinis, we love all things travel. We focus on topics relating to travel including destinations, airline, hotel, car rental and credit card reward programs. Our goal is to help people travel better. - See more at our About Us page.

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