Getting into Cuba

Travelling to Cuba as an American

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So you want to go to Cuba? Although the outright ban on Americans travelling to Cuba has been relaxed somewhat, getting there is not as simple as booking a flight and packing your bags.

The Straight and Narrow Path

Americans have only two options if they want to travel to Cuba legally: either book a trip through a tour operator licensed by the US State Department, or apply for a licence themselves. The licensed tours are themed, the itineraries are strict and there are guides, drivers and translators there to make sure you don’t slip away and enjoy Cuba on your own. All the rules and hand-holding can take some of the adventure out of the experience, particularly if it’s your first trip to Cuba. Going to the beach, dancing, drinking and other “purely recreational activities” are all prohibited. A licensed tour is not the best way to experience the “real” Cuba, but for first-time visitors nervous about breaking US government regulations, they at least offer the opportunity to see this wonderful island.

You can also apply for your own licence, but getting approved is almost impossible unless you clearly meet the requirements set by the State Department: i.e., if you’re a journalist, researcher, aid worker or student with a very legitimate reason to visit Cuba. Don’t expect to fake your way into getting a licence and then using it as your ticket to a good time on the island. You’ll be expected to sign an affidavit on your return listing contacts, places you’ve been and so forth.

Honestly, the number of rules and requirements the State Department puts on legal American travellers to Cuba makes the United States look like the Communist dictatorship, and not the other way around.

Going it Alone

As of January 2015, Cuban customs officials stamp all passports, except those of unlicensed American travellers. Of course, Cuban customs officials won’t know you don’t have a licence, so you’ll have to tell them. Don’t worry: they don’t mind. Tourism is Cuba’s main source of foreign currency and the government is careful not to do anything to interrupt the flow of travellers and their Euros, Dollars and Yen.

If you’re an American travelling to Cuba on your own without a licence, simply ask the customs officer not to stamp your passport. Practice saying “No stampa, por favor,” before you land. Millions of Americans have already visited Cuba without getting their passports stamped. This practice is gradually going to become less common as the US and Cuba continue to normalize relations, but for the time being it’s how most Americans visit Cuba. The customs officials will ask where you’re staying, so be sure to book a room at an inclusivo or a casa particular ahead of time and keep the address handy. Inclusivos are all-expenses-included resorts; casas particulares are much cheaper, privately-run apartments, and there are plenty of booking services for both online.

The threat of fines and jail time is a deterrent that keeps many Americans from trying to visit Cuba on their own. But that threat is rarely – if ever – enforced. There hasn’t been a single case of an American going to prison simply for visiting Cuba, although a handful have paid hefty fines.

Travelling to Cuba

Because of the embargo, US airlines cannot fly to Cuba, and US travel agents are barred from booking any flights to Cuba, regardless of the carrier or the nationality of the traveller. So how does an American get to Cuba? Have no fear: the “Mexican layover” is here.

When travelling to Cuba simply book your flight in person or online through a travel agent outside the US from a non-US departure point. Cancun is a popular transfer point, hence the term “Mexican layover,” but any country will do. If you’re truly paranoid – as some first-time American visitors to Cuba are – consider paying in cash to avoid having the travel charges show up on your credit card. Sorry, you can’t use your frequent-flyer miles for a trip to Cuba.

Before you book with Cuba’s national airline, Cubana de Aviacion, you should know that some of its planes date from the Soviet-era and are not exactly the latest and the greatest—to say the least. I was flying from Cancun to Havana on my very first trip to Cuba when smoke started billowing out of the ceiling. After a quick double-take and a short moment of panic, I noticed that no one else on-board (mostly Cuban-Americans bringing money and presents to their families) seemed the slightest bit worried—just annoyed by the smoke and the smell. That’s when I really began to appreciate a signature feature of the Cuban people: their ability to take failing infrastructure in stride. Don’t worry: there are plenty of other (non-US) airlines with more modern planes that make the same trip every day.

Landing in Havana

Because of the embargo, US-issued credit cards do not work in Cuba—yet. American travellers still have to carry cash or travellers’ checks, which poses something of a risk and makes them a target for the odd pickpocket. Muggings are extremely rare in Cuba, but pickpockets will single out Americans because they are known to carry cash. Violent crime is extremely uncommon, however, thanks to the authoritarian government’s harsh sentences and a pervasive police presence. With that in mind, travellers should try to keep their opinions about the Castros and Communism to themselves. Freedom of speech is still highly restricted in Cuba, and criticizing the government is a serious offence, even for foreigners.
Travellers don’t need to worry about getting thrown in jail for making an off-hand remark, but there are risks. I briefly came under suspicion while navigating customs. When asked the age-old question, “What is the purpose of your trip to Cuba?,” I stupidly replied, “to study the history of your country.” That was enough to earn me some extra time in the airport while customs officers searched my bags and translated some old school handouts I had on me. After confirming that I wasn’t a spy or smuggling classified documents, I was free to go and enjoy one of the Caribbean’s most beautiful and charming countries. Travelling to Cuba as an American isn’t easy, but it’s well worth the effort.

Related Article: If you’ve ever wondered how to sail to Cuba from America, there’s more information here.

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