There’s some paperwork in place to enter Cuba, but it’s not at all complicated. You’ll need a visa which you can buy from your tour operator, or simply pay for it on arrival (under 20 dollars for tourists). Cuba also requires visitors to have health insurance for the length of their stay, but searches for it are less rigorous than visa checks, and you could get away without it, at your own risk of course. Foreign insurers will be recognized by Cuban authorities, but you can also buy Cuban insurance at the airport for two and a half to three CUC (two and a half to three US$) per day.
Only a few establishments will accept credit/debit cards in Cuba, so cash will be vital for your trip. Customs regulations allow import of up to 5,000 dollars. Any amount larger than that will be subject to declaration upon arrival. It’s advisable to exchange US dollars to another of the currencies accepted by Cuban money exchange offices, and bring that instead. Cuba imposes a special tax on US dollar exchange, and you’ll be charged an extra 10% on top of the going exchange rate (Cuban hard currency, CUC, is artificially valued at a dollar, meaning that for every 100 dollars you’ll get 100 CUC). You’ll need Cuban money (mainly CUC, CUP—the other type of Cuban pesos—is less useful to tourists) to pay for services and products, as foreign currency is not accepted as a form of payment anywhere.
Accommodation options can be separated into two big groups in Cuba: state-run hotels and private homes—known as casa particulares, which is Cuban Spanish for “private home”. Both have advantages and disadvantages, depending on your travel plans.
Hotels benefit from their connection with the State, and generally can offer functional online booking, (very expensive) internet access, medical services, and most of the facilities and services which are standard in the industry (swimming pool, room service, tour desks, night shows, cleaning services, etc.). However, they are pricey, with star ratings that don’t always match the quality of their facilities and services, and often you may feel like you are not getting your money’s worth. Additionally, many hotels have very strict policies about (Cuban) visitors going beyond the lobby area and into the rooms, so if you are planning to hang out with Cubans, the hotels may not be your best option.
On Airbnb and other websites, you’ll find casas particulares—apartments, houses or rooms for rent managed by home owners. Quality and services in this sector vary wildly, depending on the owner, the neighborhood and other factors, but they are generally a good option, especially if you want to feel more like an explorer than like a tourist.
Internet access is very limited in Cuba, including services at hotels, where connection rates can be as high as 12 dollars per hour. Additionally, a few American service providers block traffic from IP addresses in Cuba, and you will not be able to access them unless you use a VPN. You’ll be able to do simple things, like checking your email and a few social media sites, but there’s no way to be sure if other websites will work (especially if they require a lot of bandwidth). So don’t plan on doing anything that relies on an internet connection while in Cuba.
Over the last couple of years, a number of WiFi hotspots have been installed in the main parks and squares of the country, where a service called Nauta gives people internet access at 1.50 CUC (1.50 US$) per hour. You can buy cards to connect there, but the service is slow and unstable, especially in the afternoons when the networks are overloaded with users.
No internet also means no Google Maps to guide you: you won’t be able to look for places, find ways to get there, or calculate distances. If you have a guide book or a printed map, bring it with you. You’re going to need it. Cubans are helpful, and you can always ask for directions, but it’s a good idea to have one or more maps as an aid to make your own plans. If you are able to connect to the internet, you can navigate using the map of your preference and take screen shots of places of interest. There are also some apps that contain offline maps with plenty of information on them.
Planning in a way that you don’t have to use your cell phone in Cuba is also advisable. For starters, not all telecom companies offer roaming services for their customers in Cuba, and those who do will have to charge very high rates because they need an agreement with Empresa de Telecomunicaciones de Cuba (ETECSA), Cuba’s sole telecommunications provider, which sets very high rates for most of its services. Be sure to get familiar with roaming rates before using that option. There have been infamous cases of people who were not careful and ended up paying several thousands of dollars.
From six-dollar floss to 30-dollar sunscreen, there are a series of imported products that are very scarce in Cuba, and therefore sold at three to five times the price—and those are the ones you can find. It’s a good idea to bring toiletries with you, sunscreen, insect repellent (if you are planning to travel outside the cities). If you come from Europe, make sure to bring at least one plug adapter (Europe to U.S.). A few types of over-the-counter medication (pain killers, antihistamines, etc.) would also be a good idea. Tourists cannot buy medication at the same drugstores as Cubans. There are a few places called International Drugstores that will sell tourist meds and even will fulfil prescriptions, but there’s no guarantee they will have what you need. To be safe, bring your own supply.
Cuba has very strict customs regulations, and there are a number of items to avoid bringing in your luggage if you don’t want to be stopped and searched by customs officers. In addition to prohibiting certain types of items, like drones or porn, others things are allowed only in certain quantities. For instance, you can bring your laptop as a personal belonging free of charge but you’ll have to pay over 100 dollars in taxes to bring a second one, and a third one would be confiscated. You can read the full list (in Spanish) here. Bear in mind that what you can take back home with you is also subject to customs regulations.
Public transportation in Cuba is a chore, so be ready to rely on taxis most of the time. The good news is that taxis are not that expensive for local rides, and that some of the cars offering these services are also an opportunity to ride old American models from the 1950s. The better preserved the car, the more expensive the ride. In the main cities, you will find a variety of options, including bus, bicycle and horse-drawn carriage tours. It’s also possible to rent cars, which are not cheap (prices are around US$100 per day plus a US$200 deposit, plus gas). To move from city to city, the best option is Viazul, Cuba’s long-distance bus company for tourists, since train services are also slow and in bad shape.
Most Cubans are loud, talkative and outgoing, and many will go the extra mile if you ask them for help or directions. They will go out of their way to help you find the place you’re looking for. If service personnel knock on your hotel door asking for your dirty plates, understand that they are not trying to be rude or invade your privacy, but just trying to help. That said, there are, of course, ill-intentioned people who will take advantage of you in different ways if you let them.
At restaurants, you are not expected to tip the typical 10% to 20% (like in the US); generally Cuban waiting staff will be happy if you give them anything between 1–3 CUC (1–3 US$). Bear in mind that, for example, a 5 CUC (5 US$) tip would amount to about a quarter of the average monthly salary.