Havana Nights – 5 Things I Stressed About Before My First Trip to Cuba

When one of my girlfriends asked me a few weeks ago if I wanted to go to Cuba, I did not hesitate to book my ticket. Cuba has always been one of those places that I never thought I’d see, so when the opportunity came up I had to jump on it.


There are so many fun things I could write about from this trip, but to start, I figured sharing some of my initial stressors and the reality could be helpful when making a decision to visit.

Below are just five of the topics that stressed the crap out of me and what actually happened during my trip:

Will immigration be difficult? Will I get detained in Cuba or coming back to America?

No. The immigration process was more of a pain prior to my travel date than it was actually going through it in person. No questions asked on either side.

You will need a visa to get into the country, though, which can be purchased either at the airport (there will be a stand at your gate prior to departure) or you can buy it ahead of time. I opted to buy it ahead of time through the Cuba Visa Services. They were super friendly, fast and reliable – I highly recommend!

Also, depending on what airline you’re flying with, there will be a different rate for the visa. We flew American Airlines, and our ticket guaranteed us an $85 visa bought ahead of time, or $100 if purchased at the gate. Our ticket also included Cuban health insurance which you are required to have when entering the country.


Other than those details, I was able to bring back up to US$100 of Cuban cigars and rum for my personal stash, no questions asked other than what was I doing in Cuba? Well, I was supporting the Cuban people of course – score!

Do I really need to know Spanish?

No, but it would be helpful.

I’m by no means fluent in Spanish. I took the minimum requirements in high school and haven’t looked back since. About a week before my trip I started a course on the free app DuoLingo to brush up on some Spanish words and phrases. Even though it didn’t help my fluency prior to my trip (I only committed to about 5 days max), it did get me in a better mindset for recognizing Spanish words.

I would recommend using the app perhaps minimum 2 weeks prior to the trip to make it worthwhile. It’s free and actually pretty fun to use!


If you don’t have time to brush up on some Spanish ahead of time, the Cuban people were incredibly patient and friendly to my travel partner and myself throughout our trip. We never had any significant issues getting around, ordering food and general communication.

A translator app can help to alleviate any language barriers, though. The app I used during my trip was: SpanishDict

Why I like this app? It works offline and is pretty accurate

Will I get swindled?

Probably, but it’s not the end of the world.

I thought for sure, after reading a bunch of blogs about locals pretending it was their birthdays so foreigners would buy them a drink, that I would recognize when I was being played. Fail.

Long story short, a super friendly salsa instructor and his daughter chatted up my friend and I in English. We figured since his daughter was with him that it was genuine. Wrong.

Instead of showing us a cool bar with the ‘best mojitos in Havana’, he brought us there and had a drink with us. Obviously I ended up paying the bill.

Although I was annoyed at first that I got played so hard, it was actually pretty funny and really worth the extra $4. We learned some interesting things about the Cuban culture and had a great conversation with the gentleman and his daughter.


In the grand scheme of things, what’s the harm in buying someone a drink? Also, we got the opportunity to sign our names on one of the tables at the bar. Essentially we’re now famous in Cuba. Let me know if you find our table!

How do I get around if I’m staying outside of Havana and there’s no wifi!?

Fear not! They have Uber! Kidding.

But their taxi services (depending on where you’re staying) are better and faster than ordering an Uber. We got lucky with our Airbnb located a few doors down from a busy street corner where we could hail taxis pretty easily.


Keep in mind, the local taxis in Cuba are all classic cars with the word ‘taxi’ posted on their front windshield. Depending on the type of taxi you get, you may end up sharing your ride with a few other people (think Uber POOL) or you’ll have your direct route (think UberX). It costs anywhere from $1-$50 depending on your route and where you’re going.

Either way, it ended up being super easy to get around and we were for sure riding in style.

Recommended offline map to use: Maps.me

Is it safe?

Cuba is ranked one of the safest countries for solo female travelers.

I didn’t believe that stat at first, but after my visit, I totally agree. I felt very safe in both my Airbnb and getting around town, even without wifi or a solid grasp of the Spanish language. It was a huge relief.

Regardless, still exercise normal caution. By that I mean, don’t do anything stupid or that you wouldn’t do in your home country. Being respectful and alert at all times are critical travel skills that you should always use.


Are you up for a visit to Cuba? Keep a lookout for my future posts on dining recommendations, do’s and don’ts, along with other fun tips/tricks for a seamless vacation.

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