Is it still legal to visit Cuba? - August 2019


Is Travel to Cuba Legal?

Updated August 25th, 2019

I lead group trips to Cuba and for three years, "Can I still travel to Cuba legally?" has been the most frequent questions that I get. Travel restrictions for U.S. citizens seem to be constantly changing yet the information put out by our government is consistently confusing.

Here's the low-down on legal travel to Cuba:

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Cuba Travel Policy from Obama to Trump

In December, 2014, President Obama announced moves to normalize relations with Cuba but on June 16, 2017, Donald Trump announced a directive to roll back Obama's progressive tourism and trade initiatives with Cuba. Technically, the long-standing "tourism" ban to Cuba was never lifted under Obama, it just was never enforced and steps were taken to make it easier for Americans to travel to Cuba for educational, cultural, and “support for the Cuban people” purposes. Trump's administration, however, has a VERY unfriendly stance toward Cuba and has threatened to enforce the ban on what they consider "tourism". Trump also enacted a “restricted list”, banning U.S. companies from doing business with and U.S. citizens from engaging with Cuba's military-linked entities, which control much of the island's tourism industry from hotels to buses.

What does this mean? It means it's illegal for an American to hire a Cuban tour company or take a Cuban tour bus or stay in a hotel in Cuba that is partially owned by the Cuban military. Hotels seem to be the largest concern and source of confusion since EVERY SINGLE hotel in Cuba is at least partially owned by the Cuban government and many are also partially owned by the Cuban military. Again, ALL hotels are partially owned by the Cuban government, but not necessarily by the Cuban military but you would never know which is which just by looking at the hotel. Will customs interrogate you about where you stayed in Cuba upon return to the US? Probably not. Will the US government follow up? It's too soon to tell.

One of my group tours to Cuba

One of my group tours to Cuba

Vinales Valley, Pinar del Rio

Vinales Valley, Pinar del Rio

Classic cars and classic scenery

Classic cars and classic scenery

In April 2019, Donald Trump tightened restrictions further by expanding the “restricted list”, further limiting Americans’ ability to stay in Cuban hotels, rent cars, or spending money at any establishment even partially-owned by the Cuban military. Tour operators will be audited by the U.S. government to ensure that their itineraries are in adherence with the new policy – but it's not yet clear how aggressively travel will be monitored or the audits enforced. Trump's rules will make travel to Cuba much more expensive and prescriptive but it won't change your ability to engage with locals, enjoy a beautiful country and lively culture, and have a wonderful trip.

Additional restrictions were enacted in June, 2019 to eliminate the people-to-people visa category and to prohibit cruise ships traveling to Cuba. As reported by the Washington Post, these changes also stipulated that U.S. citizens will now be allowed to sue any entity or person found to be “trafficking” in property (hotels, cruise lines, etc.) that was expropriated from U.S. citizens after the 1959 Cuban Revolution. Basically, Fidel took over the cruise ports from private families during the Cuban Revolution so technically, money from the cruise ports goes to the Cuban government and Trump doesn’t want that. Presidents Obama, Bush, and Clinton had all suspended that right, on the grounds that it would interfere with trade and national security. Apparently Trump disagrees with his three immediate predecessors. Cruse ships are scrambling to adjust routes while airlines are declaring that they will no longer accept “people to people” visa reservations.

These restrictions are also supposedly an effort to punish Cuba for its support of the Venezuelan government, which recognizes President Nicolás Maduro. The Trump administration (along with most Western countries) recognize the opposition leader, Juan Guaidó, as Venezuela's legitimate interim president.

Considering bypassing these rules and traveling to Cuba via Mexico or Canada? Think again. If you try to hide your trip to Cuba upon returning to the U.S., you will be violating federal laws and can face serious punishment.

Read on to learn more about how to travel to Cuba LEGALLY…


Legal Group Travel to Cuba

According to the Treasury Department, which licenses Cuba travel, a "traveler's schedule of activities must not include free time or recreation in excess." In 2017, Trump eliminated an individual travelers' ability to select the "people-to-people" classification on their travel form, which was the category chosen by most Americans who planned their own trips to Cuba under Obama in 2016 and 2017. However, he still allowed for group people-to-people trips, run by tour agencies and cruise ships.

The Obama Administration broadened visa categories to allow American travel to Cuba that wasn’t officially "tourism." On June 5th, 2019, Donald Trump eliminated the “people to people” travel category for groups (remember, he had only eliminated this category for individuals previously). The remaining 12 visa categories are still in place, but many do not apply to the average traveler, such as visiting family in Cuba, attending a professional research meeting, or performing at a a sports event or artistic exhibition. You can still travel to Cuba as part of a group trip with an officially licensed tour operator as long as they are using one of the approved visa categories

Again, independent travelers are barred from traveling under a privately or self-organized “people-to-people” trip but can still travel to Cuba as part of a group trip with an officially licensed tour operator that uses another visa category.

Solo Travel to Cuba

"Can I travel to Cuba alone?" is another question I get a lot. Technically, solo travel to Cuba is still an option, you just have to do it right. As an enthusiastic solo traveler who has traveled to Cuba alone at least half a dozen times, I will tell you that it can be done but given how unfriendly the Trump administration is toward Cuba and it's threats to prosecute, it' too soon to know if people will actually be prosecuted (which could include a hefty fine and/or jail time). I've worked with many solo travelers and independent groups to help them plan their own adventure to Cuba to ensure their trip is fun, safe, and legal!

Americans can still travel to Cuba on their own, you’d just be responsible to research all the current rules (and frequent changes), plan your trip accordingly, and keep supporting documentation for 5 years in case the US government requests it. Contact me if you would like help planning your own solo trip to Cuba.

EscapingNY helped me plan my own solo trip to Cuba, providing great tips for staying within my budget, and narrowing down the worthwhile places to visit based on my interests. As a result, I felt a lot more confident traveling alone and had a successful trip because of it. I recommend EscapingNY to anyone needing a trustworthy guide outside of a travel book.
— Marisa Stern, Detroit, MI
EscapingNY organized a fantastic itinerary for our family of 5 that included excellent lodgings, meals, and activities. We had so much fun in Cuba! Having a knowledgeable, engaged, organizer handling all the details and checking in with us and our hosts and drivers throughout the trip allowed for a more relaxed trip and gave us piece of mind as parents.
— Eric F, Rhineback, NY
Me in Santiago, Cuba, 2018

Me in Santiago, Cuba, 2018

The happiest car in Cuba

The happiest car in Cuba

Gibara, Holguin

Gibara, Holguin

Travelers interested in solo travel to Cuba should also consider other potential challenges, such as limited WiFi and Internet, a mostly non-English speaking population, and Cuba's two currencies, which often confuse tourists and, unfortunately, sometimes result in their being swindled. Travelers who speak Spanish will have a strong advantage but those who don't speak Spanish may have difficulty getting around and communicating in general since most Cubans do not speak English and little to no signage is offered in English. Non-Spanish-speaking solo travelers to Cuba can absolutely still have a great trip, they likely will just end up paying more and seeing less since they'll likely be at the mercy of the new English-speaking "friends" they meet, who inflate prices and get a commission on every single house, car, meal, and activity they help you coordinate.

So, what visa category do most solo travelers use?


“Support for the Cuban People” visa category

The "Support for the Cuban People" category has been very popular with both individuals and groups traveling to Cuba but the US government uses extremely vague language and does not describe specifically what is included and prohibited under this category. I’ve seen a lot of bloggers out there who visited Cuba for a week proclaim that all you have to do to fall under this category is to stay in an AirBnB and eat at a paladar. Actually, the US Government doesn’t specifically mention those as legal examples and even if they do comply with the vague “Support for the Cuban People” visa category, they don’t fulfill the required “approved full time schedule of activities.” Perhaps I should mention here there’s a lot of additional challenges with AirBnB in Cuba.

A US Treasury FAQ sheet on Cuba explicitly states that “travel to Cuba for tourist activities” is not permitted. While the overall language is vague and lacking, it definitively states that any traveler to Cuba using the “Support for the Cuban People” visa must engage “in a full-time schedule of activities that enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities and that result in meaningful interactions with individuals in Cuba” and that “traveler’s schedule of activities must not include free time or recreation in excess.”

It's unsure how long it will take for the new policies to take effect but your safest bet is to book through a tour company that has experience organizing trips to Cuba and managing visa categories and approved itineraries. No more booking your own flight and AirBnB and spending the days at the beach and nights as you please. While some people do this, “vacations” to Cuba aren’t technically legal (and haven’t been for decades!) so it’s possible solo travelers will have issues with the US government should they not properly adhere to the US government’s vague guidelines.

Havana, Cuba

Havana, Cuba

Me at the beach in Trinidad, Cuba

Me at the beach in Trinidad, Cuba

One of my group tours to Havana

One of my group tours to Havana

Restrictions on the Cuban People

In addition to imposing restrictions on American travel to Cuba, Trump also placed significant restrictions on Cubans and Cuban Americans, such as limiting how much money Cuban Americans can send to relatives still living on the island. Remittances—previously unlimited in frequency and amount under the Obama administration—are now capped at $1,000 per person, every three months.

Neither the U.S. Embassy in Havana nor the U.S. Department of State in Washington, D.C. process Cuban visa applications and many Cubans (who already have limited financial means) are forced to travel to a third country, such as Guyana, to process their visa before traveling to the United States.

The Trump administration also eliminated the Cuban 5-year visa, forcing Cubans to make a complicated and expensive trip to a third country (like Mexico or Panama) every time they wish to visit the U.S. As a result, Cubans are stuck with the B2 visa, which only allows a single entry for a three-month period. This is a particularly hard blow to Cuban entrepreneurs who rely on frequent trips to the United States to source products for their businesses that they can’t find on the island, from hair care products to baking supplies.

Trump even went as far as blocking a deal that Major League Baseball had that would have enabled Cuban baseball players to play on major league teams in the United States without defecting from Cuba, which can involve a dangerous journey at the hands of human smugglers.

Join a Group Trip to Cuba

Interested in visiting Cuba legally? Contact me to learn more about my 2019 Group Trips to Cuba!