I have dreamed of going to Cuba ever since I was a teenager standing at the edge of Mallory Square in Key West, Florida. There near the end of the square lies a certain landmark that boosts we are at the southernmost part of the continental United States and that Cuba lingers only 90 miles away.
For five years straight in the early 90s, I traveled with my family to the Florida Keys over the Christmas holidays to escape the long and brutal winter in Minnesota. We spent every New Year’s Eve in Key West, a town known for its margaritas, Jimmy Buffett and the end of the road before Cuba. I always wondered what this forbidden island was like.
Sadly, American tourists have been unable to travel freely to Cuba ever since the US-imposed embargo that severed Cuba from the United States in 1960. Deemed by many as an absolute failure, it is surprising that the blockade or bloqueo as the Cubans call it continues. But that is an entirely different issue in itself.
When the blockade was issued, travel to and from Cuba was also blocked and continued to be so for decades until the election of President Obama in 2008. Obama’s election witnessed a sudden thaw in Cuban-American relations, and over the past few years some of the travel restrictions to Cuba have been lifted.
In 2009, Cuban Americans were finally allowed to visit family members on the island and the restriction of remittances being sent to relatives living in Cuba was also lifted. Two years later in 2011, the US Government eased travel restrictions even wider by allowing Americans to travel to Cuba for academic, cultural, sports, and religious purposes. Yet Americans are still not allowed to travel to Cuba simply as a tourist making travel to Cuba one of the most unique and tempting places for an American to go.
So how can an American legally go to Cuba without sneaking in through the backdoor via Canada or Mexico? Americans must sign up for a “people to people” tour with a licensed company that provides a special travel visa through the US Treasury Department and schedules cultural visits throughout the stay. An important thing to remember is that it is not Cuba that imposes these restrictions but the US government. Cuba would surely welcome American tourists with open arms.
Given the travel restrictions, I did my homework and decided to sign up with Insight Cuba, one of the few US-based authorized tour companies that ensures American travelers are following “the rules”. The rules are quite straightforward. All American travelers must attend a full day of people to people meetings with Cubans in order to learn about the arts, history, architecture, music, the health care system, economy and other key elements of Cuban society and life. Failure to do so can lead to a tour company losing their license to travel to Cuba.
I had never done an organized tour before as I always prefer to travel independently. Yet when it came to going to Cuba, I had no choice. I soon realized that there are many pros and cons of organized tours.
Some of the most obvious cons of group tours include group dynamics, lack of freedom, too much structure and too much time spent on a bus. If you are traveling solo as well and the group isn’t good then you are in for a long vacation. Thankfully our group of 17 fellow Americans was absolutely fantastic. There was not one person who was overbearing nor were there any complainers on the trip. In fact, given our different stages in life and backgrounds we all got along fantastic and I was one of the youngest members by a good twenty plus years.
The amount of structure in an organized trip and the lack of freedom is equally an issue. In order to travel to Cuba, we needed to be in face to face meetings all day long which was exhausting, and we only had a few hours each day to ourselves. Even our evenings were busy and mostly went until at least 10 pm. The last downfall of a group tour is that a lot of time is spent traveling on a bus. I prefer to see a country on foot but there was really no way around it.
Despite the setbacks, surprisingly there were quite a few benefits about traveling on a prescheduled tour to Cuba. First of all, I didn’t have to plan a thing. Everything in the entire trip and schedule was pre-arranged including almost every single meal. All I had to do was pack my suitcase, hop on the plane and show up. Second of all, traveling on a people to people tour enabled me to see and learn about Cuban life and culture in ways I never would have if I’d gone simply as a traveler. Each day we interacted with local Cubans in a wide variety of settings. We went to a health care clinic and met a Cuban doctor who educated us on the Cuban Health Care System. We visited a dance studio to watch Havana’s dance group practice and got a chance to talk to the dancers about their lives. We had cocktails with Cuban university students who discussed the educational system and what the future looks like in the eyes of the youth. And the list goes on. Overall, during these exhausting yet fascinating meetings I took over 50 pages of notes on Cuba and felt like I’d completed a full University level class on the country. It was absolutely amazing. The final perk: As a solo traveler I was no longer traveling alone. Instead I had 16 new friends to hang out with and thankfully each and every one of them were wonderful.
Of course I would have loved to have gone to Cuba without restrictions yet I found a way to make a group-based structured tour work. As an energetic and adventurous traveler, I took the initiative to occasionally break free from the group when time allowed. I rose early and went on photo walks in the morning and also explored other parts of town during our short afternoon breaks. I was beyond exhausted and would have much rather preferred sun bathing at the hotel pool however these moments were perhaps some of my best ones in Cuba. It was time for me to take what I had learned and experienced and see for myself.
It is a huge shame that our government continues to enforce these barbaric travel restrictions and embargo on Cuba. It has been over 50 years since the blockade yet no one is able to move on and open up Cuba. What a pity. Cuba is a wonderful, welcoming country with an enormous amount of culture to offer Americans. My hope is that some day the ridiculous restrictions will be removed and all people can travel freely to this wonderful place.
Stay tuned….Much more to come on my journey to Cuba.