How to Travel to Cuba, It’s Easier Than You Think, I Just Did (2026)
I've been to Cuba twice, and it's one of the most beautiful experiences I've had while traveling. Both trips remain burned into my memory.
The first time, I went on a whim just to experience the island. I ended up meeting two amazing German guys, and we traveled the island together.
The second time, I went to fact-check what the mainstream media was saying about the island. Both times were beautiful experiences.
Traveling to Cuba can seem or feel more intimidating than it actually is.
The first step is checking the State Department guidelines (https://travel.state.gov/content/travel/en/international-travel/International-Travel-Country-Information-Pages/Cuba.html) and the Office of Foreign Assets Control (OFAC) guidelines (https://ofac.treasury.gov/sanctions-programs-and-country-information/cuba-sanctions).
The 12 authorized categories are family visits, official government business, journalistic activity, professional research and meetings, educational activities, religious activities, public performances and athletic competitions, support for the Cuban people, humanitarian projects, activities of private foundations or research institutes, exportation or importation of information or informational materials, and authorized export transactions.
The most common and best category for independent travelers is "Support for the Cuban People," which requires you to engage in a full-time schedule of activities that support contact with Cuban citizens, rather than spending time at state-run resorts or facilities. I have never been asked for a schedule or travel diary by U.S. Customs, but it's best to have a quick itinerary and maybe some receipts to prove you didn't stay at a government-run resort.
To avoid these procedures, I have heard of people flying to Mexico City and then on to Cuba, but I don't think that's really necessary, as it is very easy to just follow the guidelines.
You do need to buy a $100 Cuban visa and then fill out a traveler card to enter the country. https://cubavisaservices.com/ is great for this, as the visa is an e-visa, essentially just a visa number. You then take that number and complete the form at https://dviajeros.mitrans.gob.cu/inicio.
This is where it gets a little unusual, you have to tell Cuba you are a tourist, even though you are traveling under the "Support the Cuban People" category. You then enter the visa number you paid for into the D'Viajeros form, print it off and bring it with you( I always print off a couple and keep them in my bag just in case).
Flights to Cuba depart mainly from Miami International Airport with American Airlines, it’s a very quick flight, roughly 40 minutes to an hour.
You don't need to worry about power outages at the airport, as it is somewhat modernized and runs on generators. Even when the island experienced a total grid collapse, the airport remained uninterrupted.
As a U.S. citizen, booking accommodation is often best done once you arrive. However, I have heard of people calling ahead to reserve a room or booking through Airbnb.
Personally, I prefer to be a bit more flexible when traveling to a third world place and not prepay for a place and get stuck there. Having the option to move between different casas while you're there is really nice, as you can easily explore and switch places.
Bring cash, and a bit more than you think you'll need. I spent roughly $400 a week on both trips, and I brought double that just to be safe. They do not accept credit cards and there are no ATMs, so plan accordingly.
If you enjoy nightlife and drinking, bring a little extra, as drinks at some of the nicer places can get expensive. That said, beers at local spots are often the same price as a bottle of water.
Most places accept dollars and euros, and exchanging to Cuban pesos as needed is also possible. You can pay in any currency at most places, they may just give you change in a different one. For example, if you pay in dollars, you might receive Cuban pesos as change.
I never found that vendors short-change you or try to scam you in these transactions, it's genuinely not part of the culture. You may also notice that, depending on the exchange rates at the time, you can save a couple of dollars by choosing to pay in dollars rather than Cuban pesos, or vice versa.
Food can be as cheap as $2 at a local spot, usually just a house with a handwritten menu outside, or around $8 on average at a regular restaurant. Some restaurants are more upscale and charge $10 to $20 a meal, so it pays to explore and shop around.
Getting around Havana itself is easy and cheap. Bicycle taxis will take you most places for $5 to $10, and you can haggle on price unless you're given a fixed rate. 700 pesos, for example, is the standard fare for a colectivo(that I recieved recently), a shared taxi that stops at different points along the route to drop passengers off. They can feel a little intimidating at first, but they're chill and perfectly safe.
For getting out of Havana, say, to somewhere like Viñales, the best approach is to find other travelers and split a taxi.
It's cheaper, and you might just make some friends along the way. A chance encounter at a bus stop once turned into a shared taxi to Viñales and a group of people who became genuine friends. The bus system is another solid option, and the buses themselves are generally good quality.
The key is to buy your tickets in advance, as they sell out fast, especially given Cuba's ongoing fuel shortages, which at times leave only 3 buses operating at the bus stop I went to recently.
Booking accommodation in Cuba is simpler than you might expect. You can call ahead and reserve a spot at a casa particular, a private home that rents out rooms, or simply show up and find one when you arrive.
That spontaneity is very much in the spirit of Cuban travel. Budget around a maximum of $50 a night if you want something nice, though a comfortable casa particular in Havana typically runs about $30.
If you're happy with the bare minimum, it's possible to find a room for as little as $5 a night. Taxis to and from the airport will run you around $60, so factor that into your planning as well.
Above all, don't be afraid to go off the beaten path. Stay local, eat local, and lean into the casa particular experience, it's genuinely unlike anything you'll find elsewhere in the world.
The warmth and hospitality of the people who open their homes to you is something that stands apart, even having traveled through Mexico, China, Colombia, Spain, Vietnam, Mongolia, Costa Rica, and Panama. Cuba is truly unique, and it is absolutely worth the trip.
Kai Tutor | The Societal News Team
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