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Traveling to Cuba as a tourist is still technically illegal.
Going and returning is easy -- Cuba wants your dollars and U.S. Customs just wants to make sure you're not coming back with a suitcase full of Cohibas.
And for the most part, the one U.S. agency that theoretically cares -- the U.S. Treasury Department's Office of Foreign Assets Control, or OFAC -- hasn't made busting Americans who illegally spend money in Cuba for "tourism" purposes a priority.
There are exceptions for journalists, professional research and certain business reasons, as well as educational, religious and humanitarian activities.
President Obama made it even easier in March when he loosened restrictions to the point that there virtually aren't any restrictions at all. Obama declared that individuals could now create their own "people-to-people" experience, rather than having to go on an organized tour
For all intents and purposes, that was a game changer. If you want to go to Cuba, there's really nothing stopping you.
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Bear in mind, I'm not advocating that you go to Cuba illegally as a tourist. Far from it, I think you'll get much more out of the trip making it a legitimate people-to-people tour. You'll also have the peace of mind knowing that you did things on the up-and-up in case OFAC ever comes knocking.
I've been to Cuba three times in the past year and will probably make at least one more trip before the year is over. My first two trips were made under the OFAC exception for journalists and the most recent trip under the people-to-people exception, though it could have qualified under the journalist exception, as well.
There are only a few benchmarks that will determine whether your trip is a legitimate people-to-people experience as opposed to a Cuban vacation. First, OFAC requires that you keep a written record of everything you do during your trip -- who you talk to, what you talk about and when you talked to them. The letter of the law requires that you not have any "free time" in your schedule for things like suntanning on the beach or sightseeing.
OFAC even provides some examples of what does and doesn't count. They're worth reading. You can find them here. Basically, you need to have substantive, educational discussions with Cubans about their lives, their work and their aspirations, among other topics.
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This isn't hard to do. I've never had a problem striking up conversations with Cubans and almost everyone I've met has had plenty to say. However, can you do that for 8 hours each day?
My most recent trip was also the first one where I led a group of fellow photographers for a week-long people-to-people photo workshop. We spent a day at a farm where we talked about the farm's production and a new farm-to-table arrangement it has with one of the many new private restaurants popping up in Havana. During our week, we photographed and talked with dancers, boxers, jazz musicians, baseball players and models. We talked with local business people, students and residents of Havana's poorest neighbors.
During my three trips to Cuba, I've met several Americans who were in Cuba for legitimate reasons and others who were obviously there illegally as tourists.
I recently read a story about a photographer who went to Cuba with a bag full of school supplies so that he could claim the "in support of the Cuban people" exception. I doubt that would pass muster with OFAC.
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But my guess is that within a couple years, barring a Trump presidency, none of this will matter because all the travel restrictions will be lifted.
For now, getting to Cuba is the easy part.
Doing it legally as an independent traveler takes a little more work but in the long run will be much more enriching, albeit a little less fun, than spending the week lounging on the beach drinking piña coladas.
Joe Newman runs Focused Photo Adventures, which helps photographers arrange people-to-people experiences in Cuba, as well excursions to other locations.
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