Especially for travelers departing from the United States, going to Cuba isn't necessarily the easiest choice for a vacation. That said, it's still an ideal destination for the culture, excellent weather, and seaside lounging it offers.
But you have to be prepared when planning a trip to Cuba. In fact, travelers must have specific documents with them when they travel. If you don't follow the rules, you can't get in—so it's crucial that you plan ahead.
Along with standard items like having space in your passport for the appropriate stamps, here's everything else you need to bring to get into Cuba.
Non-U.S. Medical/Travel Insurance
While the United States has its own rules for citizens visiting Cuba (like where you can and cannot spend money), Cuba's pretty strict on its side, too. For example, all travelers must have medical insurance that's valid in Cuba—and U.S. insurance doesn't apply.
Wherever you have citizenship, you must either purchase travel insurance before departing your home country or get it at the airport in Havana. Per the U.S. Department of State, many plane tickets include the cost of insurance, too. Read the fine print carefully to find out whether your ticket covers this. You can purchase a policy for a few dollars per day that will meet the requirement and keep you from getting kicked out of the country.
A Valid Cuban Tourist Card (AKA A Cuba Visa)
First of all, Cuba is super serious about immigration and tourism. You must follow their rules or risk being arrested or imprisoned. The United States also has rules for its citizens on what you can and can't do in Cuba, so you need to be aware of that, too. And pleading ignorance on any of either country's rules won't help; you can still wind up in jail if you make the wrong moves.
So, the first step is to get your Cuban Tourist Card, AKA a Cuba Visa, before departing for the country. In some cases, you can purchase one through your airline, or at the airport. But to avoid any issues upon arrival, go ahead and apply for your card online in advance of your trip. You can use a service that processes your visa to make things easier (though there's a cost for such services).
The other option is to contact the Cuban Embassy in Washington, D.C. since you can't get a Cuban visa at any other U.S. embassy. Either way, your tourist card will only be valid for 30 days, with a maximum extension of 30 additional days. Depending on where you get it (via the airline or another source), it can cost anywhere from $75 to $85, with processing fees.
Enough Cash To Cover Your Expenses
While there's no hard and fast rule as far as cash goes, it's worth noting that Cuba isn't friendly to U.S. debit and credit cards. You can expect that your cards won't work at all while visiting Cuba, so it's crucial that you bring cash along for all your expenses. You must declare anything over $5,000 USD upon arrival, but make sure you have cash in hand to convert to Cuban pesos (CUC).
Keep in mind that the government in Cuba charges 10 percent on conversions for U.S. currency. The fee doesn't apply to electronic transactions or for travelers with other currencies. That said, it might be worth swapping your USD for another country's currency first before arrival, so you can avoid that fee. But do your math carefully to make sure you're getting a good deal!
A Cuban Passport, If You're A Cuban-Born U.S. Citizen
Yep, even if you're a U.S. citizen who was born in Cuba, you must use your Cuban passport for entering and exiting the country, says the U.S. Department of State. Basically, you're treated as a Cuban citizen the entire time you're there. This is a special note that only applies to a select few, but it's worth noting because even if you were only born in Cuba and have never returned as an adult, you'll still be held to this requirement.
A Return Ticket For The Trip Home
Because Cuba has tight restrictions on immigration and tourism, you can't buy a cheaper one-way ticket for your trip. You already need to declare the purpose of your visit and your interest in Cuba, so you don't want to cause problems by grabbing a one-way ticket and looking like you're planning to overstay your welcome.
So, make sure you have your roundtrip ticket in hand upon arrival in Cuba. That way, you can prove you don't have nefarious intentions and that you'll dutifully return home after (even if you don't want to leave!).