Of all the places I’ve traveled, I’ve never gotten more questions than I have about Cuba.

Believe me; I get it! We all are intrigued by this little country; we haven’t been able to set foot on in our lifetimes to date.

The idea that it’s stuck in the 50’s and has been completely secluded from the outside world is unlike anywhere else on earth. Since the travel ban was lifted in January of 2015, it’s caused a storm of American travelers to get on over there… Just like myself.

Driving through Havana in a classic car

Before you jump on a plane and partake in classic cars and endless mojitos, I’d like to share some of my lasting impressions about Cuba.

I won’t perform in Cuba until there’s no more Castro and there’s a free Cuba. To me, Cuba’s the biggest prison in the world, and I would be very hypocritical were I to perform there.  – Pitbull

There’s an interesting dichotomy about Cuba; the picture perfect Instagram photos seem to portray a false reality of what’s really going on. What most tourists experience is far from the actuality of what everyday life has been like for the Cuban people over the last 50 years.

The combination of communism, dictatorship, a complete lack of resources for the people, and extreme poverty can be hidden in a photo but is evident the moment you set foot on Cuban soil. Living conditions are rough; everywhere you turn you see crumbling and vacant buildings. The average Cuban income is $20 a month; most families have to ration the food they eat, not to mention there are shortages of the most basic and necessary supplies. Staples such as vegetables, fruit, and meat remain too expensive for the average household. The locals can’t afford any of the activities the tourists do; they are desperately trying to make a decent living in a country where it’s been almost impossible up till now.

Streets of Havana

There’s also a different side of history to learn. What we know from our history books, isn’t so black and white for them, they have their truth. Speaking with any of the people will give you some perspective on their reality. No one I encountered ever spoke poorly of Fidel Castro; very similar to conversations I’ve had with people in Mexico feeling favorable toward El Chapo, even coining him as Robin Hood.

Museum of the Revolution

Traveling has taught me, you have to let go of your preconceived notions and hear the other side of the story.

I was surprised at how many Cubans spoke English, much more than the few words of Spanish I know. Many talked about Obama visiting Cuba, and it was remarkable to see their excitement even over one year later. They also were very aware of what was going in the U.S. election at the time I was there and had plenty of opinions about Trump! I was certainly surprised at how knowledgeable they (and almost everyone I meet outside of the states) are in U.S. politics.

A perspective of America, Museum of the Revolution

Most Cubans were very open about not having freedom of speech and its limitations; they can talk privately about their political views but never voice their opinion in public.

They are smart, resilient, and full of pride, BUT they are ready for change. The ban being lifted for American’s to travel to Cuba is BIGGER than us. It’s a new era for them!

Colorful streets of Old Havana

I felt a sense of guilt giving into the hypocrisy by posting all the cliche tourist photos from Cuba. Like, I too was exploiting and glamorizing a country where it’s people have been suppressed for so long. The pictures don’t give it justice by any means, but once your there it’s hard to ignore what’s really going on. What I’ve learned from my time in Cuba is invaluable and has been heavy on my heart. And while I didn’t have an opportunity to make a difference on this trip, I would certainly make that my priority going back.

As you move through this life and this world you change things slightly, you leave marks behind, however small. And in return, life—and travel—leaves marks on you. Most of the time, those marks—on your body or on your heart—are beautiful. Often, though, they hurt. – Anthony Bourdain

This quote spoke volumes to my soul about my time in Cuba. Sure you can visit a place and only see the good, but that’s not the whole picture. So when people ask me about my time in Cuba, I best sum it up as incredible, eye-opening and life changing.

So if you too have the itch to check this long-forbidden Caribbean island off the bucket list, check out the extensive guide I’ve put together full of my trials and tribulations. I’ll walk you through

1. Getting There

2. Understanding Cuban Money

3. Where to Stay

3. Where to Eat and Drink

4. Things to Know Before Visiting

…All in hopes to make sure your first trip to Cuba goes smoothly and so you make the most out of it!


First up, let’s start with Part I: Getting There 

Jenny Habdas
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