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Cuba Flights, Visas and Health Insurance

These are the most common questions we get and it's tough to navigate as a consumer because the landscape constantly changes. Here's the deal...

Landing Lanes and Growing Pains

Since September of 2016 commercial airlines have been allowed to fly direct from the US to Cuba. The allowance is for 10 flights a day to 9 international airports in Cuba and 30 flights a day to Havana. We haven't seen flights increase by an order of magnitude yet but we are well on the way and the things we have seen have shown us that it is going to be a rough transition.

Just the last time we passed through we noticed:

  • At baggage check we had to stand in one line to check in with the HAV baggage system and another to check in (on a laptop) with the airline.
  • The baggage claim on one carousel was installed backwards so that as soon as bags slid onto it they were sent behind the rubber flaps.
  • The gate agent displayed the boarding group on a screen (we were flying Southwest and they board by letter and number) but never advanced it as the plane filled.

We also overheard a conversation between workers about the negotiations between the Cuban government and the airlines about who was going to pay for the improvements necessary to bring their infrastructure into the 21st century. Apparently the Cuban government thought that the US based airlines should foot that bill.



Since September 2016 the booking process has been largely normalized. Now US travelers can go to their airline of choice and book online instead of using the clunky, slow to respond and opaque charter services. In addition to booking directly with the airline several price comparison sites have begun listing direct and connecting flights from various airports via various airlines to Cuba.

Airlines that offer service to Cuba:

These flights depart from:

  • ATL
  • CLT
  • EWR
  • FLL
  • JFK
  • LAX
  • MCO
  • MIA

The following services offer cost comparison (most have many features in common so we'll list one way each of them stands out from the others):

  • Cheapair - Their 'Price Drop Payback' feature means you'll be refunded if the price of your flight goes down between the date of purchase and departure.
  • CheapOair - Have a look at their special offers for flights under $199, first-class flights, red-eye flights and more.
  • Kayak - If you are flexible with your itinerary they allow you to search a range of dates and nearby airports to find the best deal.
  • Hipmunk - Care more about the ease of your itinerary and get overwhelmed by too many choices? This site might be right for you.

AeroMexico also has competitive flights from many US airports to Havana though you'll likely be changing planes in Mexico.



All of the above providers have taken steps to facilitate the visa application process. We have seen them contract with Cuba Travel Services (CTS). You'll receive an email after purchasing your flight that explains each provider's particular partnership but they are all similar.

After you've purchased your ticket you have the option of ordering your visa from CTS online in advance for $50 plus a service fee or purchasing it at the airport for a slightly smaller service fee where CTS will wheel a kiosk up to your gate. If you choose the latter option you are advised to check-in for your flight a full two hours before departure to leave time to purchase your visa.

Either way you'll sign an affidavit declaring which of the 12 general licenses you're traveling under. Unless you are part of a special group your category is 'Educational: People to People Cultural Exchange'. Visa's are good for 30 days with the option to extend them once for an additional 30 days in country.


Health Insurance

It is still a nominal requirement that all US travelers purchase Cuban health insurance for the duration of their trip. We ask about it each time we travel and the doctors at baggage claim typically respond with 'Did the immigration official ask you for it when they stamped your visa?' in answer to our questions.

The truth is that the airlines have also contracted with ASISTUR (Cuban agency that provides this insurance) to cover you during your travels but they are shy about stating such likely due to the amorphous language from the US Department of Treasury's Office of Foreign Assets Control (OFAC). But, with a receipt of purchase for your plane tickets and boarding passes (keep physical copies of these) you should have access to the Cuban medical system should you need it.

We carry an additional form from the ASISTUR website that we present to medical providers when the need arises just to make sure there are no surprises. We also counsel our clients to purchase emergency repatriation insurance to cover the cost of that eventuality.

Tips and Tricks

  • Try and get on the 1st flight into HAV. You are going to spend 45 minutes at baggage claim. If you're there with 3 other flights it'll be more like 2 hours
  • Pack snacks and water in case you miss a meal at the airport. There are no cafes in the baggage claim areas.
  • Be creative with your itinerary. Instead of flying in and out of HAV try one of the other 9 international airports in Cuba. Holguin (HOG) is a compact and modern airport with none of the problems and congestion that HAV has.

Any Questions?

We are not just a tour operator, we are here to facilitate connections between US travelers intent upon making genuine connections to the Cuban people. If you're going it alone but want to travel well we'll be glad to to help.

  • Want richer copies of our forms?
  • Need help planning your itinerary?
  • More questions about the ins and outs of Cuban airports?

Do not hesitate to ask!

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