Growing up in Europe, Cuba was always one of the top vacation spots for many (more adventurous or more value-oriented) travelers around me. During some winters, it seems a quarter of the population of many European cities descend onto Cuba.
The special role Cuba has played in American history certainly warranted a strong response, but 50 years later it seems silly to restrict the travel rights of 300 million Americans (who have done nothing wrong) when it comes to Cuba. Now that I have an American passport, these same sanctions apply to me. So what can Americans do now when traveling to Cuba legally?
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So what has changed?
President Obama finally was able to recognize this publicly and lifted some of the Cuba sanctions. The White House issued this statement last week. Wider changes to lift the sanctions and to make travel available without restrictions needs a decision by Congress, which will likely not pass it anytime soon.
Here is what the White House wants to do:
General licenses will be made available for all authorized travelers in the following existing categories: (1) family visits; (2) official business of the U.S. government, foreign governments, and certain intergovernmental organizations; (3) journalistic activity; (4) professional research and professional meetings; (5) educational activities; (6) religious activities; (7) public performances, clinics, workshops, athletic and other competitions, and exhibitions; (8) support for the Cuban people; (9) humanitarian projects; (10) activities of private foundations or research or educational institutes; (11) exportation, importation, or transmission of information or information materials; and (12) certain export transactions that may be considered for authorization under existing regulations and guidelines.
This corresponds to the Comprehensive Guidelines for License Applications to Engage in Travel-Related Transactions Involving Cuba. Such a license can be obtained with a good amount of paperwork (most forms can be filled online though).
So far the travel restrictions remain in place, but changes may come to relax the requirements for the license, making it much easier for more people to obtain.
How do I get to Cuba?
Once you have your license, you can hop on one of the many daily (charter) flights from Miami to Cuba. On my last visit to Miami I was surprised by the sheer number of airlines operating the route, including American Airlines.
What about legal tour travel?
There's a number of tour operators that organize Cuba tours, much like the North Korean tours, with little room to stray from the group. insightCuba is one of the companies running such a tour; they also wrap up the paperwork for you.
It's not cheap though – budget $250-300 per person, per night, sharing a room, with a minimum of 6 days on the island.
What is the cheapest way to go to Cuba?
The cheapest way is to ignore the rules and take the risk of being fined when coming back.
Cuba does NOT restrict tourist visits by Americans, but is currently stamping all passports (they would not do that on request before).
Non-American frequent flyer programs (such as Avianca LifeMiles) and many others can book trips using miles to Cuba. Cash tickets from Mexico or the Bahamas are usually in the $200 range.
Make sure that you are traveling on TWO tickets, otherwise the immigration officer will see your point of departure right away.
While enforcement of the sanctions on individual travelers has been lax in the past, this can change any day and you never know what mood your immigration officer will be in. Expect a lengthy 'secondary screening' at the minimum and several thousand dollars in fines if the officer decides to pursue the case.
Cuba is an awesome destination, but it's worth waiting a couple more years until most sanctions are ready to be lifted. There are just so many other great destinations without a legal risk out there.