Q&A How to Travel to Cuba in 2019 – What Has Changed with US Travel to Cuba and What Has Not


Old_Havana_Cuba_sidestreetAs a Cuba expert with nearly a decade of trips to Cuba under my belt and one book, I have seen many phases to travel to Cuba. Since 1963, travel to Cuba for US citizens has been restricted. Depending on who was the Commander in Chief, travel has gone through easements as well as tightening of the reins. Over the decades, the largest normalization of relations between the two countries and relaxation of travel to Cuba was under President Obama in 2014-2017. However, those changes quickly were reversed by the current President Trump as soon as June 2017 when self-guided people-to-people tours were reversed. Slowly but surely, the administration has been pulling on the reins hard with an announcement by National Security Advisor, Bolton, on April 17th, 2019, announcing the elimination of all non-family visits travel to Cuba. Over the last two months, we had heard no rules nor regulations, but as of June 4th, travel to Cuba for Americans has changed, but NOT as much as the news has you believe. The BIG point is Americans can still travel to Cuba. There have been some major changes, but primarily it affects tour agencies running people-to-people tours as well as the cruise lines.

In a Q&A format, I hope to explain where we stand with travel to Cuba for Americans as of June 5th and October 25th, 2019. (Plus, more changes January 10, 2020)

Havana_Cuba_classic_Cars_bacardi_buildingCan US Citizens still travel to Cuba?

Yes, absolutely. There are still 11 ways to legally travel to Cuba via flights from the USA. The most popular category is Support of the Cuban People. You fill out your travel affidavit with the airline that you are flying to Cuba by checking the Support of the Cuban People box. You purchase your Cuban tourist visa from the airline or its provider. (As of October 25th, 2019, commercial flights from the US to Cuba will be suspended on December 10th, 2019 with the exception being flights to and from Havana. However, there will be charter flights, most leaving from Miami to other Cuban cities. As of January 10th, 2020, charter flights from the US to Cuban cities, other than Havana, will be suspended as of March 10, 2020. The only flights direct from the US to Cuba will go to Havana only.)

Then, you will need to keep a record of your full-time 7-8 hours a day of activities that show support of private businesses like BNBs, restaurants, artists, drivers, and democracy. You can do this through a travel journal, your note function in your smartphone, but also with pictures. You will need to keep these records for five years so that in the case that you are audited by the U.S. government that you would be able to prove your legal travel to Cuba.

What has recently changed as of June 5, 2019?

The quick version of the changes to travel to Cuba for US citizens is that people to people tours are no longer a legal way to travel to Cuba nor are cruise lines able to travel to Cuba. For the tours hosted by people-to-people licensed agencies, there is a grandfather clause. If there was one financial transaction before June 5, 2019, for the people-to-people tour it would be legal; however, the same is not the case with cruises. As of June 5, 2019, no cruise from the US to Cuba will be able to travel to Cuba, directly or indirectly.


What has changed as of October 25th, 2019?

Commercial flights will continue to fly to and from the US to Havana; however, as of December 10th, 2019, all other commercial routes to Cuba will be suspended.  There will be charter flights servicing many of the other major Cuban cities like Santiago de Cuba, Camagüey, Holguin, and more in and out of Miami.

Why these recent changes to travel to Cuba?

In order to get the real answer, I think you may have to tweet President Trump, but I’ll give you what I’ve read from the pundits in laywoman’s terms. Basically, the current administration is trying to financially hurt the Cuban government for its ties with Venezuela and its President Maduro. This tightening of travel restrictions is part of a portfolio of changes that are aimed at weakening the “troika of tyranny: Cuba, Venezuela, and Nicaragua.” The hopes are to get the United States’ backed President Guido into office in Caracas and implement regime change across the region.

Author_Heidi_Siefkas_of_Cubicle_to_Cuba_walking_in-Old_Havana_CubaIs it safe to travel to Cuba?

Yes, Cuba is one of the safest countries that I have traveled to in my life. I have escorted thousands of people across the island with next to no problems. As with any budding tourist destination, there is a risk of petty theft; so, zip your purses and backpack. However, in general, the crime rate is very low as the penalties are so high; plus, guns and drugs are not a problem.

Dusk_from_Morro_Havana_CubaWhen is the best time to travel to Cuba?

NOW, is the time to go and witness the beautiful culture and country yourself. Cuba needs American visitors. We are so close with so many similarities: independent spirit, salsa, baseball, y más. There are direct flights from the US on multiple carriers all year round. (After December 10th, 2019, only US to Havana flights will continue. However, charter flights from Miami will service other Cuban cities.) The high season is November through March when temperatures are mild. However, I have traveled to Cuba in every month of the year. Please note: you may find deals in the summer as well as the shoulder season when booking your accommodations, tours, and more.

Author_Heidi_Siefkas_in_Classic_Chevy_Belair_in_Revolution_Square_Havana_CubaIf you would like to travel to Cuba, NOW is the time!

Contact me so that I can introduce you to my trusted partners, agencies, tour operators, and casas in the States and Cuba. If you are interested in going to Cuba with me, I will be leading a Support of the Cuban People tour in October 2020 to Santiago and Baracoa.  (canceled per 1/10/2020 changes)

If you have other questions about travel to Cuba, here are some resources:

Cuba posts from Havana, travel tips, adventure travel destinations, and even recipes

My travelogue about Cuba: Cubicle to Cuba

If you have other questions, please leave a comment.

As always, here’s to looking up!


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