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.

Landmark in Key West Florida. Photo courtesy of Wikipedia Free Commons.

Landmark in Key West Florida. Photo courtesy of Wikipedia Free Commons.

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.

Cuban propaganda

Cubans are highly patriotic. There is also a lot of propaganda.

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.

Havana Cuba

First sight of the ocean in Havana.

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.

How would I have met and talked to Tomas if I was on the bus all day long?

How would I have met and talked to Tomas if I was on the bus all day long?

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.


  1. I really enjoy your Cuba photos. It looks like an awesome place, even if some of my friends and some Cuban soldiers traded some shots in Angola in the ’80s!

  2. I have some great memories of flying to Cuba in the early 90s – some parts were like walking into a 1950s movie set! Had a fabulous time, interesting experiences and met some lovely folks. Being a Canadian has its advantages! 😉

    1. Yes it does! I can’t believe our government still has the embargo! It is just maddening! I hope it ends soon as I am aching to go back. I really loved it.

  3. Excellent post! I am dying to go to Cuba, but I always prefer to travel solo. I hope the US will eliminate these restrictions soon. It sounds like you were lucky with the people on your tour, and it was great to learn about the culture in the face to face meetings. Can’t wait to hear more about your trip. 🙂

  4. Cuba is on my list for December this year… I’m not American so have no restrictions; however for Americans who are not big fans of government enforced organised tours (hello North Korea!), travelling independently should still be possible via a stop in Mexico, yes? I agree with you that it’s a shame the embargo is still being enforced – it has totally not achieved what it was meant to do. Great photos btw!

  5. Because of the travel restrictions and isolations hardly anything is known about the culture and people of Cuba.
    What we were familiar with Cuba are two revolutionaries “Che” and “Castro” and the Cuban healthcare system.
    Thank you so much for your stories and images from this beautiful country.

  6. My best friend in Cuenca left Cuba as an infant. He has not been back, but wants to go. My sister has been to the country twice. I desperately want to go—–so, for all of these reasons, I find these post especially exciting. Thanks for sharing your insights with us, Nicole!

    Hugs from Ecuador,

  7. Hopefully in the not too distant future this issue will be resolved. As a Canadian we truly enjoyed Cuba and are grateful to be able to just book a flight.

  8. The place is fantastic isn’t it? We always do the package hotel deal, but last trip we were invited into a local’s home and town. What a great opprotunity to see their life up close. I would love to do what you did too… and learn more.

      1. I bet. We found in the smaller areas where there are big chain resorts many of the locals prefer to work at the hotels to earn tips in the tourist currency rather than their local dollars, which is worth much less. From what we were told they pool the tips so even office staff can earn the tourist dollars.

  9. Nicole, thanks for detailing the pros and cons of a group tour. I’ve never been on a group tour before, either. My sister-in-law goes to Cuba often. She used to go to Cuba …hmmm…on the sly? But, when her long-time Cuban boyfriend died in the states, she was able to get some kind of permit to visit his family in Cuba and give them his ashes. Now, she can go freely and take clothes and other necessities for the family. I hope to be able to go with her one day. She has many, many stories about life in Cuba. I’m fascinated. Thanks once again for sharing.

    1. Thats wonderful! I wish I could go freely. Yes you can go through Mexico or Canada but I was traveling alone and also would never want to get busted! 🙂

  10. Nicole, this is a really insightful post for me. I’d be very interested in reading about the reasons of the embargo if you feel like writing a post on it! Otherwise it looks like I have some research to do! I have no knowledge of this history and am intrigued. Like you, I prefer traveling independently but this tour seems like an incredible opportunity to learn about Cuban culture and really get immersed with the people. As you said, independent travelers would miss out hugely. Cuba is a big draw for me, especially for photography reasons. However, it would be difficult for me to learn as much as you did traveling solo although after hearing about your trip I’d love to do a tour like this now.

  11. We travelled in Havana with a couple of local Cubans and heard how they live. It wasn’t good. I might have had a better imoression of the place if I didn’t know how life is for many people.
    On the surface the music is fun and the bar scene cool, but many people don’t have access to good food and basic supplies.

    1. Yes Debra. Everything you’ve said about the architecture, the supplies and shortages is very true. I haven’t dove into those topics yet but will.We meet daily with 3-4 Cubans from different walks of life and all these meetings helped us see what life is truly like there the good and the bad. I also got the pleasure of having dinner at a local Cubans house as our tour leader is Canadian and my age, and lived in Cuba for five years earlier so she was able to really help me learn about it. The apartments are very small and cramped, and the salary of Cubans is very hard. Most make about $2.50 a day and the ration cards won’t provide what they need. I will post about all these topics as time comes. I feel that our embargo and the history of Cuba has greatly set her back too. The revolution did three great things: First, got rid of the mafia and US influence of corruption. Second, brought universal health care that stays until today and all Cubans have free access to some of the best health care in the world. They also have one of the lowest infant mortality rates. Third, free education. Cuba has some of the most highly educated people in the world and their literacy campaign after the revolution got 100% literacy in one year flat. Amazing.
      Yes, communization and socialist does not work and the people are really suffering. But being in Cuba now saw it slowly beginning to change which I’ll write about soon. New laws have started allowing for free enterprise such as restaurant owners, bed and breakfasts and other services or sellers of products. That is what will change Cuba. They have two currencies one for tourist and the rich and the other for poor. Once there is one currency and more free enterprise, I think Cuba will truly push forward. Anyway, thanks for keeping me on my toes! I will move onto all these topics in due time as I find Cuba fascinating.

  12. Nicole., fellow traveler, Jean Aardweg. Enjoyed your blog and look forward to more. I was telling my son about our outrage over the embargo and he reminded me that there were nuclear missiles in Cuba aimed at the United States in the 60s and that is not soon forgotten. Something to think about from those who lived through those frightening times.

    1. Thanks Jean for the comment! Yes the Cuban Missile Crisis was very real. My dad was 17 years old and in the navy in one of the American ships there during the stand off. He said it was insane.
      The history of our relations with Cuba is very complicated as I’m learning from being there and all the books I’ve read on it. I believe the embargo today however is just hurting normal people like you and I. The Cubans who live there and are lovely people and want just to live a happy life and have supplies. They have such shortages to everything it is really sad and I know that with Raul in charge he is really trying to open up the economy and country. The Cold War was scary but it was years ago. Great points!

  13. Nicole, You’ve opened my eyes to a great travel possibility! Thanks! Like you, I have always done traveled independently. but it sounds like your experience was great. I think that having like-minded individuals together, who really want to learn about the country, culture and people, helps tremendously. ~Terri

    1. Wonderful! You and Terri would LOVE Cuba. It was one of my favorite places perhaps because of its amazing, unique history and feeling like you are stepping back in time. I highly recommend a visit and I would definitely go back in a heartbeat!

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