I just got back from Cuba, and I don’t know how I feel.

We always, strive for honest transparency in everything I share. But if ever there was a time I wanted to get it right, it was in writing this post. Before beginning part of me didn’t even want to start at all- wondering is it better to say nothing that to not say it right? How do you put such a huge, spellbinding experience into words in a way that other people can understand, so that even for a small moment they can get a glance at your experience?

Traveling to Cuba easily wins the competition for most stressful trip ever. You want to know why? I know you do. So let’s break it down…

A Whole New World: True in many many ways. For starters this was the first solo DJ less international trip I’ve been in on years. Experiencing a new place, facing new challenges, and wandering around new places without my hominid version of security blanket was different and eye opening to say the least.

On this same vibe, as an American traveler, Cuba has been closed off to us Yanks for nearly 50 years now. Experiencing the culture, interacting with the people, and just being present in the country is like stepping into a time machine, and at the same time not. Old cars, mixed with new Euro and Asian models, crumbling buildings sharing a skyline with nouveau designer hotels. Cuba was everything and nothing that I had imagined it to be.


Paperwork, Passports, And Visas: I don’t think I’ve had to jump through as many hoops since I was in elementary school and literally jumping through hoops. For real.  In all truth it actually wasn’t too bad. But I think the cultural stigma that is placed on Cuba from an American perspective gets you really worked up over making sure you have everything you need and then some to safely travel into and out of the country.

Travel Versus Tourism: I think I always knew there was a difference between these two concepts, but I don’t think I’ve ever really processed it fully until my time in Cuba.  I can say definitively we’re more travelers that tourists based on my own created definitions. I see tourism as places you go to take tours, sip margaritas on the beach, and be catered to whereas for the purpose of this post let’s define travel, as an activity outside of your own culture that causes you to grow and learn about the world through ethical and minimally impactful visiting practices.


Additionally since we’re on the topic, it’s actually quite difficult to be an “American Tourist” in Cuba.  Dependent on the visa you travel to Cuba under ( I chose people to people) you are locked in to meet certain requirements, and I know its a total bummer but apparently sipping a mojito on a beach and jamming with the locals does not qualify. If you’re wondering what those visa requirements are you can learn all about them here. Let’s get real for a second though, there are totally loop holes and ways to circumvent some of the red tape- but in all truth we chose to play it by the rules, and we still had an amazing time, have incredible memories and learned quite a bit along the way.

24 hours just wasn’t enough…

I knew when I signed up for this trip that it would leave me longing and I was right. But with changes in political atmospheres, and the possibility of the travel window to Cuba slamming shut, in my mind 24 hours was better than none. I can happily say we filled every waking moment we could immersed in the experience.

Old Havana Classic Car Tour

old havana cars

Let’s blur those lines between travel and tourism for a moment- I dare you to find yourself in Old Havana not find yourself wistfully imagining yourself riding in a classic American convertible from eras past- the draw will just be too strong! The good news is there is a way you can meet your visa requirements, learn a ton about the Cuban people and their capital city all while enjoying the wind in your face as you cruise along the Malecon in an old Chevy!

cuba mojitos

A three hour classic car tour will take you to all the highlights in Havana, and then some. Our experience with cruising through the city was everything we imagined it to be and then some. We walked through Revolution Square, breezed along the Malecon, visited Casablanca, cigar and rum shopped, and even stopped for mojitos along the way. I can honestly not think of a better way to experience as much as possible in a short time span than this guided tour.

The Tropicana Cabaret

Tropicana 1

Having only 24 hours in a place you’ve dreamed of your whole life means you’ve got to be on the go night and day. Fortunately Havana has some pretty amazing nightlife, and there is nothing more amazing than a show at the world famous Tropicana Cabaret.

Keep in mind this is NOT a locals type activity. Unfortunately a show at the Tropicana is out of the price range of the average every day Cuban and most of the people you’ll be rubbing elbows with at your shared table will be travelers as well. That however doesn’t mean you won’t have an incredible time. I’ve been to all types of live performances and this one tops them all- the colors, the costumes and the choreography will blow you away!

Make Time To Wander

Technically according to the guidelines of our “people to people” visa we were supposed to maintain a full schedule of educational activities, and we might have danced the line a little with this, but I really don’t think so. On the morning of our departure from Cuba we took our last few hours in Havana and just wandered. We photographed as much as we could, re visited some of the sites we had learned about from our tour guide, and of course did some souvenir shopping. Maybe it’s just me, but there’s no way in hell I was going to be leaving Cuba without a bag of Cuban Coffee!

Reflecting back on all that I got see and do in such a short time I can’t help but wonder all that I could have done with even more time. But no regrets. The 24 hours I spent in Cuba were some of the most magical in my life,  I’m more than looking forward to going back one day, but for now I’ve got the memories and about 1,000 photos to remind me that it wasn’t all just a dream.

Have a dream destination of your own? Some place you just have to go? I’d love to hear about it. Drop us a line in the comments, who knows maybe we’re headed there next.



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