One of the United States' most backward international relationships is, curiously enough, with a country less than a hundred miles away. If an American wants to visit or even communicate with Cuba, they have to follow a whole host of regulations from the Treasury Department's Office of Foreign Assets Control, and a couple of very lax requirements from the Cuban government. Here are the basic guidelines:

Who can go to Cuba

Cuba doesn't really care who you are or what you're doing. The U.S., however, will shit a brick. There are basically six kinds of individuals who are automatically allowed to go with proper documentation:

  1. Government or IGO officials traveling on official business
  2. Journalists with bona fide press credentials (a business card or company ID) traveling on official business
  3. Professional researchers traveling to do research
  4. Students (secondary, undergraduate, or graduate) traveling under their school's license
  5. Individuals traveling to visit Cuban family members in emergency situations (death, illness, etc.)
  6. Individuals fully hosted by the Cuban government
That last category requires some clarification. Any U.S. national can travel to Cuba, provided that they don't spend any money while they're in the country (they are also prohibited from paying for air travel on the Cuban airline Cubana, although other airlines are OK). They may bring back books or other media, but not most manufactured goods (that includes rum and cigars). All expenses have to be documented and shown to U.S. Customs.

The penalties for breaking these regulations are ridiculous: up to 10 years in prison and $1 million in fines.

In addition, a person can apply for a "Special License" from the U.S. government if they want to travel to Cuba and fall into one of the following categories:

  1. Businesspeople traveling to investigate business opportunities
  2. Freelance journalists
  3. Couriers of licensed humanitarian donations
  4. Human rights-related NGO employees
  5. Athletes traveling for a competition
  6. Clergy
  7. Educators traveling to teach
  8. Individuals traveling to appear at a public exhibition (this includes musicians, artists, trade show vendors, and the like)
Actually getting there

First, you need a visa. Cuba doesn't have an embassy in the United States, but it does have a Cuban Interests Section in Washington, D.C. that can issue official visas. If all you need is a tourist visa, then you can simply get one from a designated travel agent, or from an airline counter overseas.

The next step is booking your plane travel. If you go to Travelocity and ask for a flight from New York City to Havana, you'll get a message that says "There are no fares offered between the selected cities." Which is true: you can't just book a ticket directly from the United States to Cuba on your own, even if you have all the docs required to go.

Option number one is to contact an OFAC-designated travel agent, which can book you on a direct flight from the U.S. to Cuba. These actually do exist: most leave from Miami on Gulfstream International Airlines, although there are now a few flights from JFK on TACA as well. However, the flights are designated as charter flights, meaning that their seats are basically wholesaled out to agencies which can then resell them to individual customers.

Option number two is to connect through a third country. Most people who do this buy a ticket from the U.S. to Mexico City or Cancun, and then buy another ticket from there to Havana. This can actually be done through online reservations services, although it's pretty expensive (at least $500 for Miami-Cancun-Havana round trip on Mexicana). This method also allows the traveler to get around many of the federal regulations: in fact, if you enter Cuba on another country's passport, you really aren't subject to any U.S. regulations at all (besides the typical rules on U.S.-Mexico travel).

If you have your own airplane (or boat, for that matter), you are allowed to take it to Cuba. However, you (and all of your passengers) still have to follow the regulations like everyone else.

Unless you have a waiver from the OFAC, you can't spend more than $166 a day in Cuba. When you return, you can bring back up to $100 in merchandise, including up to 100 cigars (yay!), provided that it's all for personal use and that you don't bring back more than $100 in merchandise within any six-month period.

Again, it's important to note that all the rules are on the U.S. side. Cuba really doesn't care as long as it's getting tourist dollars. In fact, the Cuban government has already given three U.S. airlines (Continental Airlines, United Airlines, and US Airways) rights to fly directly from Cuba to most major American cities.


  • U.S. Treasury guidelines at
  • U.S.-Cuba Trade and Economic Council,

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