The first thing you should understand about this topic is that it is not allowed by the U.S. Department of Treasury/OFAC regulations. The second thing you should understand is that it is up to you to decide if you fall within guidelines of being a tourist or non-tourist.
If you fly to Cuba on a charter flight (usually from Miami), you must submit a signed Travel Affidavit to the airline, which files it away–it is not routinely forwarded to any government agency. There are several charter airlines, and each has its own affidavit. I have used one particular form for over a decade, beginning in the middle of the Bush Administration. The key items on the form I signed indicate I “will not engage in recreational travel, tourist travel, travel in pursuit of a hobby, or research for personal satisfaction only.” When a traveler signs this form, it doesn’t mean he or she can just ignore the regulations. They were presumably written originally to encourage Americans to go to Cuba “with purpose,” which seemed like a good idea 30 years ago during the Cold War. They were also written to placate the extremely volatile and bitter Cuban-American community in Miami. It was felt that, with this form, serious travelers would still be able to legally travel to Cuba, but it would also scare away the vast majority of Americans who just wanted to visit. It worked.
This non-tourist requirement has not been over-enforced for practical reasons. How can any agency “prove” that you visited Hemingway’s Countryside Villa as a “tourist,” rather than as somebody simply interested in this world-acclaimed author (i.e., you traveled “with purpose”). If you walk around Havana listening and dancing to Cuban music, who decides if you are a tourist, or if you are a music critic? YOU do. It is important to understand that travelers visiting Cuba “with purpose” are not ignoring the regulations—they are embracing them.
The guidelines are probably a pain in the butt to the Office of Foreign Assets Control (OFAC), a division of the U.S. Department of Treasury. They have much more serious issues and countries to deal with, such as those countries remaining on the U.S. List of Nations Sponsoring Terrorism—Sudan, Syria, and Iran. One of their biggest challenges today is dealing with a country which was removed from this list in 2008—North Korea. (I think this best represents the level of foreign policy expertise in the administration of our last president.)
There are many humorous anecdotes regarding the interpretation of these laws. Two years ago our group of health care researchers bumped into some other Americans visiting Cuba on a large, commercial tour, traveling on a Specific License. They had just arrived; we were departing Havana the next day for Varadero. We chatted about Cuba and told them that we were leaving “for the beach” the next day. I’ll never forget the look on the face of one of the women as she said loudly, “we were told we can’t GO to the beach!”
I eventually figured out what this probably was all about. Earlier that year, the Specific License of her tour company was not renewed in a timely manner. Travelers expecting to spend some time in Cuba were notified that they would not be able to go until the Specific License was renewed. They had to cancel their flights to Miami and their hotel reservations in Miami. There was much speculation that the license was not renewed because the U.S. Government was trying to harass companies taking travelers to Cuba. Eventually, the license was renewed, and trips started-up again.
Although it is not yet clear exactly what happened, a much more likely scenario was that the Treasury Department simply got behind in processing renewals. After all, it takes hundreds of employees at multiple levels and hundreds of thousands of pages of documents to issue a license that simply says that a company may continue to do what it has been doing for the past decade. If you’ve ever worked for any level of government (I have), you understand how a relatively simple assignment can expand exponentially to involve way too many highly-paid bureaucrats.
So about this time, Senator Marco Rubio (R) of Florida made his famous pronouncement to the effect that “American tourists are abusing the regulations–they just can’t go to Cuba, have fun, and lie on the beach at Varadero!” That apparently had a lot to do with the company de-emphasizing tourism and re-focusing on “purposeful travel.” They probably believed that their Specific License was subject to being suspended.
Meanwhile, those of us traveling on General Licenses were visiting Cuba “with purpose.” We had to stay somewhere, so we happened to book accommodations at the beach for part of our expedition. While there, we spent at least 8 hours every day engaged in purposeful activities. We were not ignoring the regulations or doing something “sneaky.” These are codified laws and regulations that apparently only our congress can change. And yet, I frequently speak with travelers who somehow still believe it makes more sense to travel to Cuba through Mexico without a license. On returning to the U.S., they plan to claim they were only in Mexico. This approach creates stress, it is pointless, and it is not a smart thing to do. Surely they can figure out a reason to travel to Cuba “with purpose.”
By the way, if you travel to Cuba with a General License through Mexico or Canada, you would only have to show it (if asked) upon returning to the U.S. No customs agent has ever asked to see mine, even though I’ve always held it in my hand along with my passport. There are no standard forms–they all look different. Years ago I included with my license a dozen or so pages downloaded from OFAC/Department of Treasury. My paperwork looked very official (because it was). These days my General License consists of just two pages—a copy of my Travel Affidavit, and another page that I create that states my dates and purpose of my travel.
So–go to Cuba “with purpose.” You can travel on your own or in a group using General Licenses. You can also travel with larger commercial operations using Specific Licenses. There are many excellent companies that are very experienced in Cuba travel. They tend to be more expensive, but they offer a wide variety of wonderful tours. The main complaint I’ve heard about them is that they were too structured and didn’t allow enough free time. If you travel with your own General License in a group and participate in group activities, it is up to you to determine the best way to research your topic.