Can an American Travel to Cuba? Are We Going to get Fined, Deported or Thrown in Jail?

Cuba was not originally on our travel plans. Our plans and goals in retirement are to travel the world slowly, spending weeks and months at a time in a particular location. Our initial plan called for 55 days in the Dominican Republic, 30 days in Paraguay, a 16-day cruise to Spain and two and a half months in Spain and Western Europe before returning to the USA for a couple of months and then most likely off to South East Asia for a couple of years.

However, a number of people have told us that we, “Need to visit Cuba before it opens up to Americans and changes forever.” We met a fellow world traveler in Punta Cana who is from New Zealand. She had visited Cuba many times in the past and urged us to travel to Cuba soon.

“It has already changed quite a bit in the past few years with a huge influx of tourists from around the world,” she told us. She also said that we could get a two-hour direct flight from Santo Domingo to Havana. So we decided to change our travel plans and take a four or five day trip to Havana while we were in the neighborhood.

Here is where it gets tricky for American citizens or residents. Since May of 1960 the United States has had a trade embargo with Cuba. This includes travel to Cuba by American citizens or resident for tourism purposes. This embargo is one of the longest running embargos in the world. I know this sounds strange to many people in countries other than the USA. Many of our Canadian friends and family have made numerous trips to Cuba. It is a popular and relatively inexpensive vacation spot and the all-inclusive beach resorts near Havana are filled with Canadian and European tourists. On paper, a US citizen travelling to Cuba for tourism can face a fine of up to $10,000!

[Note: I am a naturalized US Citizen. I was born and raised in Canada, married my American wife in 1982, emigrated to the United States in 1989 and became a US Citizen in 2006. Some people have told me, “You don’t have to worry about all this US-Cuba embargo stuff, just travel on your Canadian passport!” Although I could travel on my Canadian passport, that doesn’t really matter. The rules apply to US citizens, I am one, and to US residents, I am one of those too, even though I am Canadian by birth.]

Relations between the USA and Cuba are normalizing. In July of 2015 the US Embassy reopened in Cuba after being closed for over 55 years. President Obama is scheduled to visit Cuba in March 2016, the first time in 85 years that a sitting US president has visited Cuba.

According to the US Treasury’s Office of Foreign Assets Control (OFAC), Americans are prohibited from spending money in Cuba unless they meet one of twelve exemptions. Some of these exemptions are: journalism, religious activities, “people to people exchanges”, humanitarian reasons, education, visits to relatives, etc. These restrictions are still in effect, however, a big change happened in January of 2016. Prior to January 2016, to legally travel to Cuba, an American had to apply to OFAC and be approved to travel to Cuba. Now all the same restrictions are in effect, but you don’t have to apply and be approved by OFAC. I guess technically you may have to “prove” that you were going to Cuba for purposes other than tourism if asked, but you don’t have to get permission before hand.

In 2015, about 140,000 Americans visited Cuba, a small percentage of the over 3 million visitors to Cuba annually. This is a small number especially considering that the US is only 90 miles away from Cuba.

Today, even if you meet one of the twelve exemptions, it is still tough for an American to get to Cuba. At this point in time, there are no scheduled airline flights from the USA to Cuba. In order to get from the US to Cuba you must either take a charter flight from an approved general licensed tour company. (These tours start at about $2000 per person plus airfare) The other way is to “sneak” in from another country. For example, get on a flight from Canada, Mexico, Dominican Republic, etc. This is about to change; major US airline carriers are now applying to start regularly scheduled flights from the USA to Cuba.

So, the long and the short of it is that I feel we meet the OFAC requirements in a number of ways:

• Journalism – I have this blog now, I am a journalist, right?
• Religious – we have found a home based church group and plan to attend
• “People to people exchange” – as always when we travel, we want to meet and talk to the people as much as possible and find out about their lives.

This trip breaks a lot of our travel rules, plans and budget:

• We are only going to be in Cuba for five nights, versus months.
• We are going to be staying in hotels versus Airbnb rentals.
• Can’t use points for hotels or frequent flyer miles for our travel.
• Only bought our tickets and reserved our hotel a couple of weeks in advance.

However, we think it will be well worth it. It was an opportunity that presented itself due to us being in the Dominican Republic and it is not likely that we will be in the region again for years. We will get to see Havana and meet the people before it gets overrun with McDonalds, Starbucks and Holiday Inns. Stay tuned for more on our Havana adventures!