If you're accustomed to island hopping at the drop of a hat, understand that you will not be able to travel to Cuba at the drop of a hat. The best time to go to Cuba isn't simply a matter of weather, it's also a matter of when you will be permitted to enter the country. As a nation with a communist government, gaining entry into Cuba requires special permission. The details of entering Cuba are outlined below:
Travelers to Cuba must present a valid passport. To avoid having to update any travel documents during your stay, make sure your passport is valid for the entirety of your trip (ideally several months longer).
Tourist visas are also required for all visitors. Entering Cuba without government authorization — your 30-day tourist visa — is illegal, and can result in arrest and serious jail time. If that’s not the kind of wild trip you’re looking for, apply for a visa at the nearest embassy or consulate of Cuba.
Canadian citizens can enter Cuba without a visa if the trip is for tourism purposes, but they must have a visa for any business travel.
Vaccinations are not required to enter Cuba, though they are always recommended. An immigration officer will check for proof of medical insurance when you arrive. Cuba does not accept U.S. insurance policies. Call your insurance provider to see if you’re covered overseas, or apply for insurance with Cuba’s Travel Insurance organization, Asistur S.A.
U.S. Citizens need a special license to enter Cuba
It’s important to note that the U.S. government still does not sanction tourism to Cuba. Travel must fall into one of these 12 categories to be considered legal:
Official government work
Professional research (via a business)
Public performances (i.e., music, theater), workshops, exhibitions, athletic competitions, or aiding a clinic
Directly helping Cuban people
Research on behalf of a private foundation or a university
Exportation, importation, or informational exchange
Certain transactions (like export) may be considered for authorization.
To learn more about traveling to Cuba as a citizen of the United States, read "How to Legally Travel to Cuba As An American."
Traveling to Cuba with minors
To prevent child abductions, countries including Cuba have established entry and exit checkpoints. At these checkpoints the parent or guardian will need to provide documentation of his or her relationship to the child. This is not an official requirement of entry into Cuba, but it is recommended that travelers in question have those documents on hand, for an easier entry or departure, and to avoid potential hassles.
Register your trip
A recommendation from the U.S. Embassy in Havana: register with the American Citizens Services Unit before your trip. Visit the STEP (Smart Traveler Enrollment Program) website to register, or register in person at the very beginning of your visit at the U.S. Embassy of Havana. In a country where Internet isn’t exactly easy to come by, and your cell phone plan will not work, alerting the embassy to your basic travel plans can help your loved ones get in touch with you in case of an emergency, and help the U.S. Embassy find you and potentially rescue you in case of a natural disaster or civil unrest.
Canada offers a comparable service called Registration of Citizens Abroad, with a simple sign-up process to keep Canadians safe in their world travels. Both STEP and the Canadian program also offer travel alerts, so travelers can have up-to-the-moment advisories on security risks. This allows them to make informed decisions about their travel plans.
When you enter Cuba you must provide proof of your departure.
Do your research
This isn’t an official requirement, of course, but ensure that you know the rules that will affect you before your visit. OFAC (Office of foreign assets control) has certain regulations — for example, persons authorized to travel to Cuba may purchase alcohol and tobacco products while in Cuba
for personal consumption. Authorized travelers may also return to the United States with alcohol
and/or tobacco products acquired in Cuba as accompanied baggage for personal use. OFAC
considers “personal use” of an imported item to include giving the item to another individual as a
personal gift, but not the transfer of the item to another person for payment or other consideration. Find up-to-date information on the U.S. Treasury's website.
Read our extensive list of Frequently Asked Questions by travelers visiting Cuba. You can always ask an Anywhere expert to answer your questions and concerns via chat, phone call, or a travel planning request.
When you finally arrive in Cuba, you will (technically) have multiple options for getting around. However, much like gaining entry, this island nation is not without its quirks — it's also not as tiny as travelers seem to think it is when they actually try to traverse it. When traveling around Cuba, we recommend that you book private transportation. If you plan on flying whilst on the island, be sure to book your flights in advance, you do not have to pay a departure tax in Cuba anymore, it is now included in the cost of your airfare.