What You Need to Know to Get to Cuba

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¡Hurra! Cuba, the island less than 90 miles south of Florida, is now open to US citizens again!

But don’t book your flight just yet. While the US and Cuba have re-established diplomatic relations, it’s not quite as easy as simply hopping on a plane and returning to a place once admired for its beautiful beaches and party atmosphere – Cuba is still a closed communist country, and you’re going to have to work a little.


First, a little history: Cuba, prior to Fidel Castro’s 1959 revolution, had become little more than a vast tourist destination for the wealthy. Money did not trickle down to the locals, and Castro referred to the country as the “brothel of the Western hemisphere.” His successful takeover of the country led to a decades-long standoff with the US, which did not care for Castro’s cozy relationship with the U.S.S.R. – or Castro’s decision to nationalize everything from oil refineries to banks, many of which were once owned by US interests.


The crisis came to a head in 1961 and 1962, when a failed CIA-backed Bay of Pigs invasion and an attempt to introduce Soviet missiles on the island brought the US and the Soviet Union to the brink of a nuclear exchange. Tensions cooled, sanctions from the US took over, and Cuba and the US largely ignored one another for decades – until July 2015, when diplomatic relations were restored and embassies re-opened.


But sanctions, and the privations of a communist economy, have left Cuba’s development frozen in time, and a journey into a country that has had little participation in the rest of the world’s development since the 1960s is catnip for a certain kind of traveler. Three million people visit Cuba every year – but prior to the sanctions being lifted, just 140,000 of them were Americans.


As of right now, only a certain kind of American traveler can visit. Here’s what you should know before you even attempt to go:

Is it now legal to hit the Cuban beaches for a getaway vacation?

Nope. General tourist travel is still disallowed, and you can be fined or put in jail.

What is new?

Rather than requiring a license and a specific reason for going (like research, or working), travelers only need a tourist visa and a signed affidavit from a travel provider indicating your reason for going. You’ll want to keep records and receipts for five years afterward.

Who can go?

You must fit into one of 12 categories in order to go to Cuba, and you’re the only one who has to decide what applies to you (believe it or not, at the moment it’s kind of an honor system). (Here’s a PDF of all of the ins and outs, from the Treasury Department: https://www.treasury.gov/resource-center/sanctions/Programs/Documents/cuba_faqs_new.pdf ]

These categories are:

  • Visiting family
  • Humanitarian projects or to provide support to the Cuban people
  • Official business of the US government, foreign governments and certain intergovernmental organizations
  • Journalistic activities
  • Professional research
  • Educational activities by persons at academic institutions
  • People to people travel
  • Religious activities
  • Public performance, clinics, workshops, athletic or other competitions and exhibitions
  • Authorization to provide travel services, carrier services and remittance forwarding services
  • Activities of private foundations, research or educational institutes
  • Exportation of certain Internet-based services

So how do you get a visa?

For about $25, you can get the visa through travel agents that specialize in the country like Cuba Travel Services or ABC Charters. You can also go through CheapAir.com to book your flight only, and they will help you get your visa.

Another option is hiring a fully-organized tour through companies like HavanaVIP Tours , which has a number of educational and historically-based guided tours that will not only introduce you to the area, but help with providing a reason for your visa. But bear in mind: You really can’t skip out on the tour – if you’re found to have spent a lot of time outside your stated reason for going, you’re in just as much trouble as if you hadn’t obtained a visa in the first place.

There is another way!

Yes: You can skip some of the hassle of going to Cuba by not flying directly. If you catch a flight from Canada, Mexico or the Bahamas, you won’t need to obtain your visa in advance – you can get it at the gateway country’s airport during your layover.

How much will this cost?

At last check, May flights from New York City’s JFK airport to Havana started at around $800. Naturally, flight prices will vary, and you’ll want to have someplace to stay once you’re there, so keep an eye on your budget.

Note: This information should not be taken as complete legal authorization for a Cuba journey; it is provided here for entertainment purposes only. Consult a travel operator for specific information on how you can make your own trip happen.

Randee Dawn is a contributor for InsureMyTrip and can be found at randeedawn.com and @RandeeDawn on Twitter.

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