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    Everything You Need to Know to Plan the Perfect Trip to Cuba

    Photo: Trisa Taro

    By Trisa Taro.

    Cuba is one of the most vibrant and wonderfully frustrating places you’ll ever visit. Its growing—but lagging—connectivity and stunted infrastructure are part of the many reasons that exploring the beautiful country will be an adventure of a lifetime! Not to mention the strikingly dilapidated facades and untouched landscape are a photographer’s dream. 

    Photo: Trisa Taro / View across the beautiful city of Trinidad

    For Americans, traveling to Cuba seems like an exotic fantasy. Thanks to the diplomacy of former President Obama, gateways to Cuba are now open and more accessible than they’ve ever been to US citizens. And airlines and travel agents have jumped into the now-open market—which means it’s easier and more affordable for you to travel to Cuba! Despite these recent developments, finding clear information and getting answers to your planning questions isn’t as easy. Luckily, we’ve got you covered. Here is everything you need to know to plan the perfect trip to Cuba:



    As of September 2016, eight U.S. based airlines offer non-stop flights to Cuba. Flights originating in the U.S. currently depart from New York, Atlanta, Miami, and Orlando. These non-stop flights service to nine cities in Cuba including Havana, Camagüey, Holguín, and Santa Clara. As tourism expands—and it’s expected to—you can anticipate more flight routes to become available.

    Visa Procedures

    Getting a visa for Cuba (referred to as a Cuban tourist card) is easier than you think! Traditionally, you would book your flight and then apply for your visa either through a third-party operator, a travel agent or directly with a Cuban embassy. If you were flying via Mexico or Canada, you could purchase your tourist card at the airport or on the plane.

    Now that you can fly directly from the States, U.S. airlines also allow you to purchase your tourist card at the boarding gate before your departure. So you don’t need to worry about getting one before you fly! The cost of the tourist card is $50 but can vary based on which airline you fly so check ahead of time.

    The tourist card is valid for a single entry for a period of up to 30 days. Upon arrival in Cuba, a portion of your tourist card is retained by immigration authorities and you hold on to the remaining portion until it’s collected at the airport prior to your departure. It’s important that you don’t lose the second half of the tourist card because you won’t be allowed to leave the country without presenting it at passport control!

    Photo: Trisa Taro
    Photo: Trisa Taro
    Photo: Trisa Taro

    About OFAC Certification and “People-to-People” Licenses

    Legally speaking, U.S. citizens are not permitted to travel as tourists to Cuba. U.S. law restricts travel to Cuba to 12 authorized travel categories, each requiring travelers to meet certain requirements. The categories include: family visits; official business of the U.S. government, foreign governments, and certain intergovernmental organizations; journalistic activity; professional research and professional meetings; educational activities; religious activities; public performances, clinics, workshops, athletic and other competitions, and exhibitions; support for the Cuban people; humanitarian projects; activities of private foundations or research or educational institutes; exportation, importation, or transmission of information or information materials; and certain authorized export transactions.

    So how are most people getting to Cuba? Answer: under the travel category “Educational activities and people-to-people exchanges”. The category is relatively broad, only requiring people traveling under this category to have “a full-time schedule of educational exchange activities that will result in meaningful interaction between the travel and individuals in Cuba.” Traditionally, this is why Americans traveling to Cuba would have to go as part of organized, sanctioned trips (usually called people-to-people exchange tours).

    Now, you can travel under the “Educational activities and people-to-people exchanges” category without an organized tour group. You can go solo, with a friend, or your own group so long as you technically fulfill the category requirement. You are supposed to have a prepared itinerary and keep receipts of all your engagements (museums, business cards, etc.) in the event that OFAC chooses to audit you—which is nearly unheard of. But, of course, better safe than sorry.

    When you arrive at the airport before your flight, you’ll be required to sign a form certifying that you are traveling under one of the 12 travel categories and specifying which you are traveling under.

    Medical Insurance

    In addition to the tourist card, you’ll also need to obtain Cuba-specific medical insurance. Luckily, airlines have also helped streamline this process. Most include a temporary policy within the cost of your ticket. Delta, for example, automatically includes a medical insurance surcharge of $25 in the cost of each passenger’s fare. The boarding pass will serve as evidence of the insurance policy should any emergency medical services be required during the trip. If you are able to obtain your medical insurance through your airline, be sure to hold on to your boarding pass during your entire stay in Cuba.


    According to most travel sites, high season for Cuba is November to March when the weather is dry. The flip side is that crowds are heavy and prices are a bit steeper. If you’re going during Christmas or New Year, definitely book in advance. Low season comes in May and June when there’s a risk of hurricanes. Shoulder season in April and October still offers decent weather at lower prices and with fewer crowds.


    Like most countries, Cuba has a variety of accommodation options for you to choose from. Luxury hotels, mid-range hostels, economical homestays—the works. If you really want to immerse yourself in the Cuban culture and lifestyle, opt to stay in “casas particulares.”

    Casas particulares are private homestay options akin to your typical Airbnb private room rental. In addition to being kind to your wallet, staying in a casa gives you a far more interesting and personal view of the country. Casa owners are sure to make you feel like family. You can book ahead of time (more and more owners are beginning to advertise on sites like Airbnb), helping to guarantee you get the quality and comfort level you want—or inquire as you go. It’s easy enough to walk from casa to casa and ask about availability. You’ll be able to spot casas by the blue and white signs on the doors of the buildings, marked “Arrendador Divisa.”

    Photo: Trisa Taro / The outside of a local casa in Trinidad

    Throughout our trip, we saw people backpacking around town looking for a place to stay for the night. It’s important to keep in mind, however, that during peak or holiday seasons, availability may be limited and it might be better to call or book ahead.


    In general, 2-3 days in each city is a good place to start. Depending on how much you want to see and do, you could stay a bit longer. If you want to try and hit two or three major cities, we’d suggest at least a week or else you might feel rushed and not have enough time to really soak everything in.


    Within cities, taxis and pedi-cabs (called bici-taxis) are the easiest way to get around. Negotiate a price before getting in!

    To get from one city to the next, for example from Havana to Cienfuego or Trinidad, the best and most reliable way to get around is by bus or car hire. In some cases, you may be able to fly between cities, but flights are often pricey and don’t save you that much time. Unless you’re going from one end of the island to the other, you may be better off with ground transportation.

    Photo: Trisa Taro / View of the local bus station in Trinidad

    Víazul is the main long-distance bus company used by visitors. Schedules are regular, the buses are air-conditioned, and bookings can usually be made in advance at the company offices located within the city bus stations. For popular routes (e.g. Trinidad to Havana or Havana to Viñales) you’ll want to book as far in advance as possible because seats usually sell out. Fares are reasonable and run anywhere from 10-15 CUC for short haul trip (2-5 hours), and 20-35 CUC for long-haul trips (i.e. 5+ hours).

    For added flexibility, comfort and efficiency, hiring a car with a driver is a great way to get around. Car hires can be private—where it’s just your party and the driver—or shared, where you combine your party with others to fill all the spots in the car/van. Obviously, a private car hire is more expensive, but the cost of a shared car hire is comparable to bus fares.

    Photo: Trisa Taro / Riding in our shared taxi from Cienfuegos to Trinidad
    Photo: Trisa Taro / Riding in our shared taxi from Cienfuegos to Trinidad

    In our experience, to go from Havana to Cienfuegos on our shared car hire was 25 CUC per person and got us there 2 hours faster than the bus would. To go from Cienfuegos to Trinidad was 15 CUC per person; and Trinidad to Havana was 30 CUC (it was slightly cheaper because we were in a large group van with 6 other people). The cars and the drivers vary by quality and the price you’re quoted before isn’t always indicative of the quality of the car or the driver, so if you can, it’s best to organize these ahead of time through your casa owner, who can recommend a reliable one.


    There’s so much to do in Cuba. Between museums and historical centers, you’ll have plenty to keep you occupied during the day. But don’t stress too much about planning everything you’re going to do. Part of what makes Cuba so interesting is its natural beauty, striking architecture, and vibrant atmosphere. You’ll likely spend most of your time wandering the streets, whether that’s the music-filled alleys of Havana or the cobblestone lanes of Trinidad. Embrace the Cuban lifestyle and be ok with going where the wind takes you!

    Photo: Trisa Taro / The sights of beautiful Trinidad, Cuba – known for its untouched colonial architecture
    Photo: Trisa Taro / The sights of beautiful Trinidad, Cuba – known for its untouched colonial architecture

    If you’re keen to learn more about the sights and attractions, you’ll want to grab a travel guide! Because of the limited internet connectivity in Cuba, you’ll rely pretty heavily on your guide book—it’s one of the few places where you see people carrying them everywhere they go! 


    Cash & Exchanging Money

    You’ve probably heard that Cuba has two currencies, but don’t worry, it sounds more confusing than it is. For basic purposes, all you need to know is that Cuba operates on a double currency system: convertible pesos (CUC$) and Cuban pesos (MN$). As a visitor, you will use exclusively CUC and all prices are listed in CUC unless otherwise stated. Some travel guides and sites say that you may want to have some Cuban pesos on hand for small street purchases (like fruits or candy) but even in non-touristy areas, most places accept CUC.

    While some travel experts report that the use of credit cards and ATMs are becoming more and more common in Cuba, cash is still king. You’ll want to carry cash with you and then exchange it to CUC when you arrive in. Euros, Canadian dollars or British pounds are the best currencies to carry because they give you the best exchange rate. US dollars are also accepted but incur a 10% fee, which is why you’ll probably want to exchange your USD to Euros first before you leave and then exchange your Euros to CUC when you arrive. It’s important to note, however, that you should check the exchange rate from USD to Euro first. If you’re debating what to do, my suggestion would be to carry Euro, as it’s more common and universally accepted at all currency exchanges.

    Regardless of what currency you carry, the rule of thumb is to take more cash than you think you need. As a reference, for two people for 8 days, we spent 700 for food, drinks, transportation, and other incidentals (note: we paid for accommodation prior to arrival). We were frugal but didn’t skimp on nice meals or the obligatory mojito (…or two… or three). 

    Photo: Trisa Taro / Line outside of a casa de change in Cienfuegos

    Changing money is relatively easy but comes with its own interesting hoops. You can exchange currency at specific bureaus (called casa de change), at some banks, and at some hotels. Keep in mind that when you arrive at a casa de change or bank, you’ll need to wait in line which isn’t always as straight forward as it sounds. Queuing in Cuba takes on a new form, where people look for the back of the line and claim their spot by using the person in front of them as their place holder. Then they’ll go off to do something else and come back to the line later. So don’t be startled if you start to notice people coming in and out of the line—it may seem like they’re cutting but really they’re just resuming their place in the queue. Locals will always be honest so you don’t need to get frustrated, – it’s just a way of life!  

    Internet and Wi-Fi

    It’s well known that Cuba has limited connectivity to the Internet but getting online isn’t as hard as it’s made out to seem. The country’s internet access is run by a single company called Etecsa. To get online, you’ll have to buy a prepaid user card from one of their sales booths or store fronts around town (be prepared to queue). You’ll also see men on the streets and in the public squares selling cards— – most are legit but buy at your own risk. Once you have a user card, head to any one of the public Wi-Fi spots around town. These are usually big public spaces like parks. You’ll know you’re near one by the crowd of people glued to their devices. Despite the fact that connectivity is improving, connection is still slow so you should plan to use it sparingly. Personally, we used our 7 days in Cuba as a digital detox and really enjoyed being completely off the grid.

    Photo: Trisa Taro / Etecsa booth, where you can buy a Wi-Fi, in Cienfuegos


    Tipping is important and expected for most services in the hospitality industry—at restaurants, in hotels, and the never-ending musicians/bands that will serenade you during meals. 

    The pace of life in Cuba is slow and easy-going. Everything from meals to transport go at a glacial pace (with rare exception) so be prepared to be patient and go with the flow.

    Language can be a barrier for many visitors who don’t speak Spanish. Outside of the heavy tourist areas, you’ll find limited English. Most travel guides have a Spanish glossary with key phrases that you can default to. You can download Spanish translation apps before you go—but make sure they work offline since you won’t always be connected to Wi-Fi.  


    Going to Cuba is sure to be a once in a lifetime experience! Because it’s still a bit unknown (at least for most Americans), you may feel a bit nervous before traveling—but don’t worry! Locals are helpful and nearly everything you need can be figured out once you arrive. Plus, anything worth knowing about beforehand you just read above! Enjoy and let us know how you like it!

    Trisa Taro (@trisataro) is a self-taught photographer and creator of the travel blog, The Free Passport. Born in Honolulu, Hawaii and raised in Los Angeles, California, she now lives and works in New York City. To see more of her Cuban adventure, check out her Instagram, Pinterest, and blog!

    stevie benanty

    stevie benanty

    Founder of a conversation.

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