I have always been a fan of winging it. Some people spend months planning out every little detail of their trip to a foreign country. I prefer to fling myself into unfamiliar circumstances and figure everything out when I arrive. Having the luxury of time (between sailing contracts), I am usually able to find great deals and stretch my hard earned dollars as far as they can go. I find that some of my fondest memories of travel come from being willfully unprepared. When it comes to Cuba, though, there were a few things I wish I had learned about beforehand.

After spending nearly a month on this beautiful Caribbean island just south of Miami, I have finally realized all of the things that I should have known BEFORE I traveled to Cuba. I hope that this list can help you to avoid some of the problems that I ran into! Here are a few things that you just NEED to know before you hop on that plane.

Playa Ancon, Trinidad de Cuba

1. Wi-Fi will not save you.

When I arrive in a new country with lots of questions about what to do and where to go, I always refer to my most trusted resource – the Internet. After having survived “The Great Chinese Firewall” I figured Cuba would be a piece of cake in comparison. Well, I was wrong. Wi-Fi does exist in Cuba but it’s a little more difficult to use than I thought.

In order to purchase a Wi-Fi card you will have to locate an Etecsa provider. You can ask your host to point you in the right direction by asking for a “tarjeta” for the internet. It costs $2/hour and you can buy as much time as you’d like after waiting in a long, long line. In order to use the wifi you will then have to locate a public square where the wifi signals exist. Even when you get online you will not be able to download certain apps or access certain websites. Basically, don’t rely on the wifi to save your life, but only use it to check in with family and friends.

  • Use the google maps on your mobile device to load up the detailed maps of the cities that you intend to visit in Cuba. Even if you are not connected to wifi, the GPS in your phone will still work, which can be a lifesaver.
  • Make sure to set up auto-pay and take care of any bills that may come up before your travels, as you will not have access to your banking websites.
  • Download all necessary apps BEFORE you get to Cuba.

This is the Wifi Card – $10 for 5 hours

2. It’s NOT difficult to go through customs as a US Citizen. 

This has been the biggest concern that I’ve had to address from people online. If you fly directly from the US you may have to pay an additional fee for a tourist card (anywhere from $25-$90 depending on if you only have USD or a currency with a better exchange rate). Canadian airlines generally cover this fee in their ticket price. When going through customs they will check your travel insurance and ask what you are doing there. My boyfriend had an English-speaking customs agent and she asked him two questions:

Q: Why are you here?

A: I’m a travel photographer.

Q: Who do you work for?

A: Myself, I have my own website.

That was the extent. I did not have an agent who spoke English so she didn’t ask me a single thing about why I was there.

I would recommend making up a mock itinerary (or a real one if you’re that organized!) They did not ask either of us to show it, but it made me feel more comfortable to know that I had something that detailed the plan for my trip in case they asked. Here’s a sample of the basic itinerary that I drew up – this is not how our trip ended up, but it was a rough outline and would have probably been enough to satisfy the agents.

3. Buy Travel Insurance.

Okay, I did have travel insurance because I always travel with World Nomads*. If you’re from the USA and you’re traveling to Cuba they will absolutely check on this and you must have proof of insurance. (Yay! I don’t need to give my whole spiel on why travel insurance is so important – Cuba says you have to have it, so just do it!) Also, it’s important to note that the Cuban healthcare system is very good. If you run into any medical problems while you’re traveling in Cuba you will be taken care of!

Have a screenshot of the receipt captured on your phone or carry a printed copy, just make sure you buy before you fly otherwise you will end up having to purchase their plan at the airport!

If you’re going on a shorter trip you might want to check out IMG Global, which offers a better rate (with inferior coverage).

Because with health insurance, it’s better to have it and not need it than to need it and not have it! 

4. Book your first night, but then rely on the Casa Particular network.

I would absolutely recommend staying in a Casa Particular for the duration of your trip. A Casa Particular is a house with extra rooms that locals rent out to tourists. We booked our very first night on Airbnb and then used the “Casa Particular network” for the rest of our trip. We were visiting in November, which is not technically high season, but there seemed to be far more casas than tourists (except in Viñales – Viñales was almost totally booked up).

What is this “network” that I speak of? When using Casa Particulares, hosts will recommend you to a family member or friend in the next city that you’re traveling to. Usually that person will meet you at the bus station holding a sign with your name. They will walk you to your casa. Always ask for a casa with a central location.

One pro tip that we learned from Don’t Forget to Move is that if you are relying on this network, you will likely pay the same price at the next casa that you paid at the last. If you book an expensive room for your first night you may want to go on foot to find a cheaper one for the next night.

We paid an average of $20/night per room (split by two) with some occasionally going as low as $15/night (when we went hunting for deals) and never more than $25/night. If you don’t like the looks or location of a casa, never feel obligated to stay there. Chances are there are 20 others just down the road waiting for you! Here’s a video I made about Casa Particulares if you’d like a little more info:

5. Download a Spanish Dictionary that Works OFFLINE.

We didn’t do this. We should have done this. This one is free and works great. ’Nuff said.

6. Buy the Lonely Planet Guide Book.

We were absolutely kicking ourselves for not having purchased this essential reading. Everywhere we went, we saw happy travelers pulling out their guidebooks to read up on history and figure out where to go next. Even tour guides used the Lonely Planet* to refer to maps. Unfortunately we didn’t have this luxury and we definitely wish that we did. Because I never purchased the book, I can’t really tell you what’s in it – but I wouldn’t go back without it! I also recommend downloading the Triposo app and the Cuba Guide within the app so that it is accessible offline. Together, these guides should make your life a whole lot easier!

Experience Valley de Viñales by horseback.

7. Read up on your History.

Growing up in the US, I was always taught one side of the story with Cuba. There were a few things that I learned in Cuba that helped me to understand that there are two sides to every story. At the same time you want to be able to identify fact vs. propaganda. When visiting the Museum of the Revolution I was a bit shocked by how much information seemed misleading.

If you’re heading to Cuba, think of it as a great opportunity to give yourself a refresh on what’s been going on. Knowing what the government has been up to for the last few decades will definitely help you to understand the Cuban people a bit more. I would focus my studies on the topics of:

  • The Cuban Revolution
  • Fidel Castro & Che Guavara
  • Cuba/United States Relations

These people and events have shaped the reality for Cubans for decades. There are tons of documentaries, books and podcasts on these topics – make sure to educate yourself on BOTH sides!

Museo de la Revolución two days after Fidel Castro’s Death. 

8. Cuba is SAFE, but be smart.

I honestly feel that Cuba is one of the safest countries I have ever been to and it’s also the only country in which I’ve ever been pick-pocketed. How can both of those things be true?

Well, walking around, talking to locals and spending time in Cuba made me realize that people there really don’t commit violent crimes. There are extremely long jail sentences for even the most minor crimes, so it doesn’t happen very often. Being in a country like this for three weeks led me to drop my guard and I was a victim of a crime of opportunity.

I left my camera pouch of my backpack unzipped with the camera lanyard hanging out and someone grabbed it. Cuban people are not generally violent but they are also living on an average of $30/month. If someone dangles an opportunity like that in front of them, crimes like these are bound to happen.

Sharing a laugh with an armed guard at the Che Guevara Mausoleum.

9. Make a Realistic Budget.

If you’re from the US, you will have to bring all the money that you plan to spend with you. US Bankcards and Credit Cards still do not work in Cuba. Make sure to come up with a realistic budget that you will be able to stick to – and then leave a little wiggle room! Also if you’re coming from the US, keep in mind that the currency exchange rate from USD is very bad – consider converting your cash into Canadian Dollars or Euros before you head to Cuba.

My average spending for the trip came out to about $42/day. While I’m certain that budget backpackers could easily spend less, I was also pretty conscious of my spending and seldom splurged. If you don’t plan on eating like a local for at least one meal per day and if you’re a little rusty on your haggling skills you may want to budget for more.

My expenses for the 28-day trip were as follows:

Food: $335.55

Transportation: $285.50

Accommodation: $266.50

Excursions: $119.00

Internet: $63.00

Average per day: $41.51

Here’s a detailed expense report from my trip:

Because nerds like me enjoy numbers! 🙂 

10. There are two types of currency – if you’re traveling on a budget, you’ll want BOTH.

The CUC, pronounced “kook”, is the main tourist currency and it is always equal to 1USD. When you ask how much something costs they will give you prices in CUC. Whether it is a Casa Particular, a menu or a knickknack on the street – people can usually tell you’re a tourist and they will charge you for it.

The CUP, or as they call it “moneda nacional” is 25 = $1. If you want to try eating like a local, there’s tons of street food priced out in national currency. We ended up ordering a plain egg omelet on toast for breakfast for around $0.15-$1 per day. You can find local eats by noticing sandwiches in the windows of little shops on the side of the roads or by seeing a large group of locals standing near a window on the street.

Make sure to exchange your money at the airport and ask for at least $10 worth of moneda nacional. They may insist that you will not need it but you should insist that you will! Don’t mix the currencies up…

The local currency.

11. Transportation is expensive.

If you do not plan on traveling from coast to coast, this will likely not be an issue for you. When putting together my expenses from the trip, however, I realized that transportation was more expensive for me than accommodation. If you plan on renting a car, you will spend even more but you will be rewarded with much more freedom – just make sure you’re comfortable driving on some pretty bad roads!

There are two main types of transportation for tourists if you don’t plan on renting a car: the Viazul Bus and the Collectivos. We traveled mostly by bus because the prices were almost the same and the buses were more comfortable. That being said, the Viazul busses are falling apart. Many have broken seat backs that will automatically recline so far that you’re nearly sitting in someone’s lap. If you get on to the bus early check your seat backs and check those of the seats in front of you! Also, the busses are very cold, so bring layers!

If you’re planning your whole trip in advance, I would recommend booking your bus tickets ahead of time on the Viazul website. It will not let you book unless you are planning more than a week in advance. If you plan on figuring it out as you go, just be aware that even if they say the busses are sold out you can request to put your name on a waiting list. Always show up an hour before the scheduled bus you’d like to be on. Normally, enough people won’t show up and you will make it on your desired bus without a problem.

The collectivo drivers will definitely try to convince you that their way is better than the bus. Many of them boast that they will get you there faster. This is usually true, but you definitely pay in comfort and sometimes in cash!

Collectivos – the cars are beautiful but after a few hours the novelty fades. 

12. Go with a friend! It’s MUCH cheaper.

We met a few solo-travelers in Cuba and they were paying the same price for a room that my boyfriend and I were paying combined. Unfortunately for the solo-travelers, the rooms are usually set up for two people so the casa owners are not usually willing to cut you a break. We also stayed in a few rooms that could easily accommodate up to four people. If you’re traveling as a larger group, you will probably save even more money! Thank you to Travelstache (my travel companion) for advice and photos to make this post more complete!

Action Items:

  1. Pin this post for later and share it with friends!
  2. Buy this book*.
  3. Download these free Apps: Triposo (and make sure to download the Cuba Section). Spanish Dict.
  4. Make an itinerary.
  5. Make a budget.
  6. Convince a friend to go with you.
  7. Read up on Cuban History.
  8. Buy Travel Insurance*.
  9. Ask any questions you may have in the comments below!

All items marked (*) are affiliate links. If you purchase something through one of these links I will be given a small commission at no extra charge to you. I would never recommend something that I don’t believe in and this is one small way of helping to keep this blog running!