Rules About American Travel to Cuba Have Changed Yet Again

havana cuba
Photo by Karel Miragaya

Cuba has become like that significant other you can never quite seem to break up with. They push you away, only to pull you back. Then you push away, but they reel you back in again.

For decades, U,S. citizens couldn’t go to the island nation. Then, in 2015, President Obama relaxed restrictions on American travel to Cuba so some of us could.

Now, some of us still can, but not as many as before. The bottom line is that President Trump would like to make it very difficult for you to get to Cuba. The Washington Post reports he’s looking “to steer economic activities away from the Cuban military, intelligence and security services … and encourage the government to move toward greater economic freedom.”

But, what does this mean in practical terms? Let’s unpack it for American travelers.

First, while “tourism” to Cuba is technically restricted by the embargo, Americans can still legally visit. There’s an entire niche within the travel industry — including cruise lines, commercial flights, big-name hotel brands, Airbnb, and dozens of tour providers — with an active, vested interest in accepting and working with American travelers to facilitate their visits to the island. However, under the new regulations, planning a visit to Cuba now requires a few additional hurdles.

The caveats are more like speed bumps than insurmountable roadblocks of red tape. In broad terms, individual visits to Cuba will, for the most part, no longer be allowed. Visitors must be able to prove to the U.S. government’s satisfaction that their itinerary includes meaningful daily interaction with locals in an effort to directly bolster the Cuban economy through private enterprise (and not the Cuban military). The U.S. government’s interest here is that American travelers are not patronizing businesses owned by the Cuban military. Unfortunately, the list of banned businesses — including many restaurants and hotels throughout the country — is extensive and not always clear. The only easy way to satisfy this is to plan your trip with a group tour as they ensure that your entire itinerary is above board.

If group travel tours aren’t your thing, it’s still possible to book an individual trip to Cuba. You must first fall under one of the 12 authorized categories of travel to Cuba. For the everyman, the only viable categories are as a journalist (for, say, bloggers), or for educational or religious activities (both of which are vaguely defined). However, individual travel to Cuba under even these three categories can be tricky. On your return to the U.S., you’ll need to prove to Customs and Border Patrol that you had daily, meaningful interactions with Cuban locals. What this means in practical terms is almost impossible to define. Individual travelers will be much more heavily scrutinized in this regard. To dodge any potential conflict by unknowingly staying at a government-owned hotel, travelers are best served by crashing at casa particulares. Most of these are basic Airbnb rentals that involve renting a room or an entire apartment directly from a Cuban citizen.

It’s worth noting that anyone with existing travel plans to Cuba will not need to cancel their trip. Although the new regulations went into effect in November, administration officials have confirmed that the revised ban will not impact anyone who’s already booked a flight, cruise, or tour.

Feature image by Karel Miragaya.