5 challenges you’ll face in Havana, Cuba and how to overcome them

If you’ve never visited before, some aspects of culture Havana, Cuba will surprise you at first. Here are five challenge you’re sure to experience after arrival.

1. Feeling terrified your taxi will run someone over

Taxis are the main mode of transportation around Havana and the rest of Cuba as well. We read that the driving was crazy before we arrived, so we were somewhat prepared for that.

Drivers used their car horns on a wide range of occasions—equally when they were happy and when they were upset—at other taxi drivers, at pedestrians, and at their friends. If you are out walking in areas like Old Havana (Habana Vieja) where the streets are very narrow and used both as a road and sidewalk, and hear a horn, it’s best to move to the side as quickly as possible.

I knew that Cuba would have many classic cars. But still, I was somewhat surprised just how many there really were. Almost every taxi we took during our stay was a classic car. Some were nicer than others but all got the job done.

Cuban tourist taxi, classic car

2. Wishing you had paid attention in high school Spanish class

You won’t run into many fluent English speakers in Havana, so it’s important to arrive with at least some basic Spanish phrases. I studied by listening to the first two seasons of Coffee Break Spanish starting a few months before departure. By that time, I could confidently use the basics: greetings, introducing myself, ordering food, telling a driver to turn right or left, saying I don’t understand, etc.

Despite this, I couldn’t understand too much. I would say that Cuban Spanish speakers spoke very quickly, even after realizing I knew an only a little of the language. Every little bit of preparation counts.

Even in casas particulares, the go-to overnight accommodations in Cuba, hosts didn’t know much English. And, of course, I’m not saying that I expect them to. As travelers, it’s easy to assume that people in the tourism industry will know the basics of English because it is so often as a universal language.

At the same time, I would say that the hosts are the most patient and will take the time to speak slowly and repeat themselves as necessary so you can practice your Spanish (the taxi drivers, understandably, do not have time).

3. Saying to say “no” after dozens of requests from strangers

Everywhere you turn in the city, you’ll find someone selling something. To make ends meet, many locals have several side hustles, many of which are aimed at tourists. Some sell fake cigars on the street (as you’ll see in any guidebook, you should always buy these in shops). Others get a commission for getting you to eat at a certain restaurant.

If you’re a thrifty traveler like me, then these have real potential to screw up your budget for the day.

My fiancé, Ethan, is a total yes-guy and hates to tell people he’s not interested. I will admit that we ended up at a couple restaurants because of very persistent people standing outside rather despsite being uninterested in the restaurants themselves. In all of these situations, it’s best to learn to say “no” and move along.

4. Being completely confused about where to find wifi and how to buy it

Accessing internet in Cuba is a pain, but after your first time, it will be no problem at all. Read my full guide on buyinggRead my full guide on buying

Read my full guide on buying
Learn how to buy wifi and log on here

5. Relying on offline maps

Numbers four and number five run hand in hand. Because you won’t have data, you’ll need to download an offline map app on your phone before you arrive in Cuba. It’s possible to download an app there, but it will take forever.

I used Maps.Me (iPhone app, Android app), probably the most popular offline map. You’ll need to download the country of Cuba ahead of time.

I typically rely on Google Maps, but it doesn’t allow you to download a whole country in the same way.

I would recommend doing a test run ahead of time while you’re back home. I’m not too directionally challenged, but I struggled to get used to the interface. If you’re too short on time to do a test run, watch this quick YouTube tutorial.

Offline map screenshot on Maps.Me
On Maps.Me, I really liked using the compass function when turn-by-turn directions became confusing. It can at least point you in the right direction which is always a good start!
Challenges of a Cuba vacation
5 biggest challenges of a Cuba vacation

Read how I built a legal itinerary as an American citizen here.

3 thoughts on “5 challenges you’ll face in Havana, Cuba and how to overcome them

  1. So many great tips! I went to Cuba almost 9 years ago, so I wonder how much it has changed since then. Will pin this for when I go back 🙂

  2. Cuba is on my bucket list so these tips were really helpful, especially about the phone data and offline maps, which i usually don’t use. Oh, and I cannot wait to ride the classic taxis 🙂

  3. I totally agree with all these points you made. This post made me smile as I borught back all the memories of trying to get by with next to no spanish. My Guide Book became gold dust – with other travellers constantly asking to look at it, taking photos of information, as there was no internet access. 🙂

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