Cuba: Traveling Off the Radar

For American travelers, Cuba remains one of the last tantalizing forbidden travel destination spots in the world. While Americans may not want to visit some other countries, they can go almost anywhere with relative ease. Officially, though, Cuba is off the American traveler's map. or so it seems.

The laws regarding Americans' travel to Cuba are complex, requiring patient scrutiny, a high tolerance for bureaucracy, and a long wait for those who wish to visit Cuba under officially sanctioned pretenses, which are shrinking exponentially each year.

For those Americans who are committed to the idea of traveling to Cuba and who are willing to avert the hoop-jumping of doing so legally, a trip to Cuba can be surprisingly easy. By using a third country as your point of entry to Cuba, you can visit the not-so-forbidden country with minimal risk. Throughout the history of the decades-old embargo, which does not prohibit travel but rather the expenditure of money in Cuba, Americans have been using Mexico, Jamaica, Canada, the Dominican Republic, Costa Rica, The Bahamas, and Panama—to name just a few “gateway” countries—as the jumping off point for Fidelandia. Mexico, in particular, does a brisk business in providing flights for Americans en route to Cuba, with multiple daily trips departing from Cancun and Mexico City and landing in La Habana.

What it takes for the curious and committed American with a serious interest in Cuba is some travel smarts provided by other travelers who have taken the route before. Here is some advice of seasoned U.S.-Cuba travelers with experience circumventing the travel sanctions. While conditions will vary depending on many factors-some of which are beyond your own control-following these tips will smooth your passage.

Understand the law. Even though you're skirting the law, it's critical that you understand it. First, it's crucial that you know what the penalties are if you are indeed sanctioned and whether those are worth the risk required based on your own circumstances. It's equally important, though, to read the law carefully and understand your rights (visit http://www.treas.gov/offices/enforcement/ofac/ programs/cuba/cuba.shtml). In the unlikely event that you're confronted at US Customs and Immigration and asked whether you're returning from Cuba, have an answer prepared. Visit online travel forums and familiarize yourself with the experiences of other U.S. travelers who have made the trip to Cuba using gateway countries.

Choose your gateway with care. There are many factors that determine what gateway country is best for you. The price point of the ticket from the third country to Cuba is likely to be your main consideration, and it will help if you look at a few gateway countries and track price trends for a couple of months prior to your trip. Flights to Cuba from any gateway country and on any airline are notoriously unreliable (delayed or cancelled), so consider gateway countries that offer the maximum number of flights and flexibility. Otherwise, you're likely to find yourself spending extra travel dollars on the unplanned expense of lodging in the gateway country. Also examine which airlines offer service between the gateway and Cuba. The more airlines providing service, the more attractive the gateway will be, as flight schedules are more likely to fit your transit needs.

Prepare your paperwork. and your pesos. U.S. laws regarding the use of passports for border
crossings have changed in the past year, and it is not quite as easy to travel to Cuba now as it was two years ago. It is still possible, though, and the more identification you carry with you (passport, birth certificate, driver's license), the better off you are, and the more prepared you are with pesos, the more likely you'll be to facilitate your border crossing process. When traveling from the U.S. to Mexico, for example, you will need to show your passport to U.S. and Mexican officials, and you will have your passport stamped upon entry to Mexico. You will also have your passport stamped upon exiting Mexico on your way to Cuba, though Cuba will not stamp your passport. Upon return to Mexico, your passport will be stamped again, but a $20 bill folded into the passport and delivered with a polite request upon exit and re-entry to Mexico in transit can often avoid stamping. When you re-enter the U.S., you simply say that you visited Mexico.

Understand ticketing processes. You can not use a U.S. credit or debit card to make flight reservations to Cuba, even if you are purchasing the ticket from a gateway country's airline (such as Mexicana or Air Jamaica) by phone or over the Internet. You can, on occasion, get lucky and ask a phone agent to hold a reservation for you, but more likely than not, you will need to purchase your ticket once you have landed at the airport in the gateway country. Again, do your homework. Know what airlines offer flights, on what days, and at what times. Time your flight arriving from the U.S. accordingly, and proceed to the counter of the gateway airline with cash to purchase your Cuba ticket. You will also need $15 for a tourist visa, which the airline will sell to you with your ticket.

Entry and Exit Requirements in Cuba: When entering Cuba, you should have the name of a hotel or casa particular prepared to offer up to Cuban immigration officials, who can decide at whim whether to verify your reservations and, in the event you don't have them, compel you to make them before leaving the airport. Be sure to hang onto your tourist visa, as you'll need it upon exiting Cuba, and don't forget to set aside 25 CUC (the Cuban currency) for the required exit tax, which you'll pay at the airport on your day of departure.

As with any trip, the more you know, the more prepared you'll be, but nothing will compare to your own first experience. If you do decide to travel to Cuba, you'll be joining a group of passionate travelers whose first trip was not their last, and you'll build your own list of tips for traveling off the radar.