What’s it like to travel in Cuba in 2023?

I’ve been spending the last 12 days here in Cuba, learning about the culture, the people, the rich history, and the complex dynamics of their relationship with the United States. I have more words to say than can fit into a single blog post, and I’ll be sharing more now that I’ll have access to wifi and some time to reflect. 

Cuba isn’t a place to be afraid of. 

In fact, its people are some of the kindest and most generous I’ve met, even though they have so much less than we do. 

I’d also be remiss if I said that being in Cuba is all about riding around in classic cars, exploring beautiful beaches, and sipping mojitos.  

Sure those things exist here, but if that’s all you come here for, you’re missing out on the real Cuba and an amazing opportunity to give back. 

What I’ve experienced over the last 2 weeks will be burned in my memory for the rest of my life. The Cuban people welcomed me into their homes, and they treated me like family, cooking meals, making cafecitos, and sharing about their lives and their country’s sad and complicated history. I’ve laughed so much here, but I’ve also shed a lot of tears. 

Why the Cuban people need us more now than ever

The Cuban people desperately need our help, as the very same government that is supposed to advocate for them keeps most from succeeding. It’s heartbreaking, and it’s something many turn a blind eye to because, to be frank, it’s difficult to witness, especially when there are problems that can’t be solved with money alone. 

But we can use our privilege to help the Cuban people. That’s why I came here—to learn firsthand how we can do just that and to learn the ins and out of how to travel here. It’s not something you can just read about online.

It’s honestly a place that has to be experienced firsthand to truly understand it, but the United States has made that a challenge for Americans in recent years. 

What is it like to travel to Cuba?

I know traveling to Cuba is intimidating for many—it was for me too. And quite honestly, after being here, I’ve realized it’s even more difficult than I’d anticipated, especially after the devastating impact of the U.S. sanctions and the pandemic, which have kept an already repressed people even more repressed and set the Cuban people back even more. 

Combine that with a general lack of wifi access, online banking, and the digital, modern world we’ve all become reliant on, and you’ll soon realize why traveling to Cuba on your own can be extra cheallnging for the novice traveler.

Although the U.S. has banned tourism for Americans to Cuba, we can still travel under supporting the Cuban people as one of the 12 permitted OFAC categories for travel. 

But Cuba lacks the infrastructure of most places we typically visit. It’s a complicated country, and traveling here can be a challenge if you haven’t done your research (and even then, it’s still tricky). As a professional traveler, I can say with confidence that traveling to Cuba is a whole different ballgame, and I’ve deeply benefited from the knowledge and experience of locals who understand how to navigate this complex world that’s set back in time. 

And you will too, if you choose to join me on my group trip to Cuba at the end of 2023. 

With the help our local Cuban friends (and a savvy Brit with strong Cuban ties) we’ll be going on the adventure of a lifetime and get to see a side of Cuba that most tourists never get to experience if they go on their own. 

My new years group trip will focus on giving back to Cuba and its people in all the ways we possibly can. We’ll share our resources and our time with the Cuban people, and they will share their homes, their stories, and their hearts with us. And if you’ve traveled with me before, you know we will be having a shit ton of fun along the way. 

Sign up for my Cuba waitlist to be the first to know when my trip launches later this month. If you decide to join me, I promise it’ll be one of the most rewarding experiences of your life. 

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More Than Just a Tourist in Cuba

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My First Travel Tattoo