Ways to Go
Since the U.S. is the only country in the world prohibiting its residents to visit Cuba, this page is geared toward U.S.travelers. For regulations regarding travel for U.S. citizens, including changes since Obama’s December 17, 2014 announcement to normalize relations, see the U.S. Treasury Department website.
Authorized Independent Travel
Probably because it’s buried amid the bureaucratic language of a dense government document, many people are not aware of the Treasury Department’s General License. This authorization allows professionals and students conducting research in their fields to travel to Cuba without requesting official permission. What this means is that if you are, for example, an artist or a musician or even a zoologist and you meet with others working or studying in your field, which can be as simple as going to galleries, attending concerts, or visiting and speaking with the employees at the zoo, you are legally permitted to travel to Cuba without a tour group. Period.
Bring business cards, slides of your artwork, CDs of your music, photocopies of published writings in your field, etc. or evidence of your enrollment in a university program in case you are questioned by immigration upon your return to the U.S.
Unfortunately, a General License does not allow you to fly directly to Cuba on one of the legally-sanctioned charter flights, but via the Dutch-run website www.cubajunky.com you can purchase your flight to Cuba (from a third country) ahead of time. Cubajunky also has information if you want to pre-book a casa particular, a private house that rents out rooms to travelers and where you can stay—and often have homemade meals—with a family. If you want to meet Cubans and experience the realities of everyday life in Cuba, I highly recommend this option over staying in a hotel.
If you cannot find any way to fit into any of the broad categories of people authorized for a General License, traveling to Cuba in protest of the embargo (this is what Pastors for Peace does) is always an option, and one that comes with more backup support than many people realize.
Technically, what’s illegal is not the travel but the unconstitutional prohibition against it. As such, there are many lawyers willing to work (quite often pro-bono) on your behalf should you be stopped upon your return to the U.S. (neither Cuba nor any third-country you need to pass through will stop you from entering Cuba) and later receive a letter leveling a fine against you. For more information, contact the Center for Constitutional Rights (http://ccrjustice.org/).
Authorized Group Travel
Below are organizations that have received permission from the U.S. Government to take groups to Cuba. Not surprisingly, since these are package tours, the cost will be triple to quadruple (or more) what it would be if you traveled on your own. But these tours do offer a legal way to go to Cuba and, with the permission they grant you, often you can stay on legally on your own after the tour ends. Check with your tour operator to verify this, but this is how I first went to (and stayed on) in Cuba. Global Exchange is generally the most affordable of the operators listed below, but some of the other operators offer specialized tours that are not offered by Global Exchange. I will update this section regularly as I learn of new trips—please feel free to contact me with any I should add. Good luck and happy planning!
Center for Cuban Studies
For a more comprehensive list (too extensive to include here), check out the Latin American Working Group: