U.S. Politics and Travels to Cuba

Travel from the U.S. to Cuba was banned in 1962 following the Cuban Missile Crisis as part of the embargo or “blockade” against Cuba.

In early 2009, U.S. President Barack Obama eased the travel ban for Cuban Americans. And for the first time in decades they could travel the 103 miles between the U.S. and Cuba freely.

Less than 2 years later, he eased the ban again and allowed missionaries and students to travel to Cuba. As more and more American’s were finding a way to Cuba through humanitarian initiatives, journalistic activities or by flying indirect routes – my social media feeds were flooded with pictures of the brightly colored, ornate façades of crumbling buildings, the equally vibrant 1950s classic cars, and stunning crystal clear waters of its beaches. I had to go there.


I only knew of Cuba what I learned in history books in school, from reading books by Ernest Hemingway and by (no shame) watching Dirty Dancing 2: Havana Nights. The history books made it a scary, awful place – communists, missiles and desperately poor people; the pop culture told a different story of people radiating passion and sensuality.

While Cuba has been called a time capsule of sorts by American’s, the people there didn’t just freeze in time. Despite lacking much of our modern technologies, Cuba was very much alive all of these years. Just out of our view, they were still dancing to the Buena Vista Social Club and hanging by the Malecon. They were living, and figuring out their way of life inside of this new government system.

In the Fall of 2014, Obama announced the intent to re-establish relations with Cuba. He met with Cuban President Raul Castro the next April, and throughout the rest of the year his administration worked out new licensing that would ensure safe aviation between the countries, and widen the accepted rationale for travel. However, change takes time and it wasn’t until November of 2016 that American airlines started their first routes to Cuba. And in 2017, I was among the 600,000 American’s who legally traveled (the only 90 mile journey) to Cuba for the first time in over 50 years.

Visiting Cuba, Finally.

Once Southwest kicked off their flights to Havana, my flight attendant roommate and I were stoked and started doing research into what we needed to do to get a visa and to go. Originally, I thought I’d be writing a blog post that explained that process and how we actually made it happen – but at this point it’s pretty much null and void. The visa we used is no longer allowed/available because the guy running things these days decided to roll back pretty much everything Obama did, including easing travel between the US and Cuba. With that said, after going to Cuba, I can confirm that you need to go… and soon. While I’ll keep my fingers and toes crossed that the next lady or gent in office revisits the issues again, it seems that American’s best bet for seeing Cuba nowadays is on a day or overnight trip while on a cruise.

This article “Yes, Americans Can Still Travel To Cuba” gives a pretty good overview of the current options for traveling to Cuba.


Getting to Know Cuba

Before our trip we did lots of research on what to expect, how to stay safe, what to pack, what to eat, and what to do. While most of these things were easy enough to get right, we realized our research on how to stay safe was completely irrelevant. We had read blogs and articles from travelers who either got it all wrong or just had an entirely different experience. We went into the trip somewhat afraid of being surrounded by poverty – we were sure that we’d be brokenhearted at every step as we turned down requests for rice, toothbrushes or milk. We were prepared to wear money belts to hide our limited CUC. We planned to be guarded always; we had several people warn us of the dangers of Cuba (all of whom had never been). But, our experience included none of those things.

Our trip to Cuba was incredible – the people were kind, friendly and sincerely interested in getting to know about us and our life in the US. They did not beg for anything, in fact they seemed somewhat content with what they had, yet hopeful for a more fruitful future. They were ecstatic about better relations with the US, but fearful our reunion would bring drugs, weapons and crime to their country. They were generous, charismatic, genuine and just as colorful as the classic cars and bright façades of their vibrant country.

Discovering Colorful Cuba – A Vibrant Cultural Experience

I plan to write up a few more blog posts about our trip – what we saw, who we met, what to pack and what we’ll never forget. But until I get to doing that (TBH, posts are few and far between these days), here is a preview of the first few days of the trip to hold you over:

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