Is it Safe to Travel to Cuba Right Now?

Our favorite Cuban cowboys and drivers from our most recent trip to the island. [January 2026]

I just returned from over two weeks in Cuba, and as always when I leave this beautiful country, my heart feels pulled in multiple directions.

As you may know, after running group trips to Cuba for the past three years, I wasn't planning on running any more trips to Cuba until our political situation in the United States feels a little more...stable...

I think it goes without explaining that the last year living in the United States has felt contentious, and every week it feels like there’s another headline about our tumultuous relationship with another country. Continuing to run Cuba trips felt risky as a business owner, and so many variables are outside my control. Running group trips is hard enough, and all of the external factors at play make things extra challenging.

But Cuba has this special way of reminding me what actually matters. It reminds me of my privilege—that I get to complain about things like spotty WiFi while people there are navigating power outages and oil shortages with more grace than I could ever muster.

It reminds me that I'm stronger than I think I am. That perspective and resilience aren't just buzzwords—they're survival skills. And honestly, it's a reminder I need at least once a year.

The question I keep getting asked is: Will you be going back next year?

A few weeks ago, the answer was no. The political climate, the government restrictions, Venezuela, the power outages, the oil shortages—it all felt like too much. There are so many twists and turns happening so rapidly that it's hard to keep up.

But then again, it's always something in Cuba. And that's exactly what makes this place so special. The way people here persist through impossible challenges and just make it work.

My love for Cuba runs deep. I hate the idea of pulling back trips that support so many people. I hate the idea of not seeing the locals who have opened their homes and their hearts to me and my travel community—people we've genuinely come to love and who rely on our tourism to survive. Our trips are the highlight of their year, and they seemed devastated to learn that our temporary breakup with Cuba is indefinite.

I know many of you want to return to Cuba to see the people you've come to know and care about, and there even more of you who haven't been yet and are dying for the chance to experience it before it changes even more—or before the opportunity disappears altogether.

So here's where I'm at…

It's still undetermined, but it's likely I'll be running one New Year's trip in late 2026. There's a lot at play right now with politics, the state of Cuba itself, and changes within my own business. I'm not going to offer a trip unless it's going to become a reality, so for now, I'm collecting interest and making a tentative plan with the intention of opening it in spring for booking if things feel stable and there's enough interest.

If Cuba is on your heart, join the waitlist, and mark your calendar for December 27, 2026 - January 3, 2027.