90 miles to Cuba. How to get there?

Once the wheels of our American Airlines charter plane screeched on the runway, signaling that we had landed on Cuban soil, a roar of applause started. Nothing surprising so far, we Romanians do the same once we land to safety. The difference was I had just landed in Cuba, on a plane full of Americans, myself included. The only ones applauding were the Cuban Americans, visiting their families. The rest of us still had our noses pegged to the window.

Jose Marti Havana Airport

After a slow walk down the stairs of the aircraft and unto an unusually windy Havana, I notice the irony of things, now at a safe distance; the biggest letters, reading American, right in front of Aeropuerto Internacional Jose Marti – La Habana.

American Airlines lands in Havana, Cuba

Ever since the US embargo on Cuba in 1960s, Americans have all been forbidden to travel to the Caribbean Island, famously known to be only 90 miles from Florida’s southernmost point. In recent years, since President Obama’s election, travel restrictions to Cuba have been significantly loosened. Beginning with 2009, Cuban Americans could now visit their families. Two years later, in 2011, Americans were now allowed to travel to Cuba, provided it was for educational, cultural or academic reasons, on the so-called licensed “people-to-people” tours. This was us. We were on the Undiscovered Tour with Insight Cuba.

Passport control was again, of no surprise to me. Long lines formed in an orderly fashion, in this no-fuss dreary hall. We are in the terminal for U.S. flights only.

My turn comes. I speak Spanish to the officer, she replies in English. Okay … I think to myself, first sign of hostility. We’re not allowed to smile either. I would later discover this was the first and last encounter with a non-smiling, unfriendly Cuban.

She stamps my passport and visa. That’s right, she stamped my passport. One of the many changes undergoing in Cuba is all passports now get stamped, American or not.  In bright pink, no less, the last color I had expected to see. And then, as if stepping unto a magicians’ studio, I grab the doorknob to the door in front of me, turn it and enter the baggage claim area. I am officially on the other side. 

As expected, the sole baggage claim belt is a torturous, slow display of packaged goods of all sorts – big screen TVs, appliances, and boxes of clothes – all brought from Cuban Americans to their less fortunate relatives. Some of these items can now be found in Cuba, but for an outrageous price tenfold their worth.

A flustered American lady left her passport in the bathroom, someone frantically signals. Definitely to be avoided. To lose your passport in Cuba is like getting locked up and throwing away the key.

A long wait later, we exit the arrivals door unto a crushing amount of people. Their expression says it all. I can instantly pick up on their anguish. Most are waiting, with their hands clenched on the railing. Few feet behind, others are crying, in a long embrace. I can’t tell if they are reunited or saying goodbye. Most brought their extended family, to welcome a loved one they had not seen in two-three years, perhaps 20. Travel to and from Cuba is now less prohibitive but no less bureaucratic or expensive. Few have managed to leave Cuba, even once.

Next stop, before we journey into Havana, is the Cadeca, where everyone exchanges money. Our credit and debit cards are useless pieces of plastic here, and so cash is king. Cuba operates on a dual-currency, the Cuban peso and the CUC, the Cuban convertible peso – what all foreigners use – the equivalent of a dollar. The commission is crushing. For $300 USD, I get about 260 CUC.

With fresh bills in our wallets and our cameras eagerly waiting to snap, we officially start our journey.


Before I delve into the incredible odyssey that Cuba meant, it’s important to discuss how we got here and most importantly, what can one expect from going on a people-to-people tour.

Right from the get go, I was warned such a tour would allow no freedom and would only encourage the propaganda. There is certainly a lot of debate, along with a certain bias, regarding these cultural exchanges to Cuba.

Viva Cuba

However, the point remains Americans can’t travel legally to Cuba, unless through an OFAC licensed tour; or other nationalities for that matter, if traveling from the US. The only way would be through the back door, via Canada, or Mexico, at your own risk.

I had my own concerns surrounding this type of trip. How would I genuinely experience Cuba on a fully scheduled tour, with 20 other people? Surely, as a dual-citizen, I could find other ways to come independently. I soon found out, that this was in fact perhaps the best way to do it.

What usually sucks on group tours – given you don’t know anyone beforehand, and if you’re traveling unaccompanied as I was – are group dynamics, lack of freedom, and a certain routine. In my case, none of these were an issue.

1. Group dynamics – I had the great luck and honor to travel with a very well traveled group of individuals, cultured, easy-going and with a sense of humor. Most of them had traveled far and wide in the world – and thus had my full respect – and some were at their multiple trip to Cuba. Many were interested in the political aspects surrounding the island, and so, I was in for a two-week intense boot camp, of learning both from the local Cubans we met along the way, as well as from my fellow travelers. I was by far the youngest, in most cases, by decades. but somehow, after the first day, I didn’t even think of it.

2. Lack of freedom – I was concerned I wouldn’t have enough time to wander on my own, to get the vibe of a new place, to meet random people or to take pictures; in a nutshell, to form my own opinions. While it was a heavily scheduled tour, one I’ll need months to fully disseminate, I also had plenty of time for myself. I left the group several times, and managed to blissfully get lost through the streets of Cuba. I indulged in photo sessions and went out to discover Cuba by night. I spoke to anyone I felt like doing so. Not once did I feel like I was on a leash.

The other issue of concern was not knowing how freely I could engage in certain topics. Having been born in a former communist country, I was advised by my parents – as I was when I went to China for a month – to be careful what I say. Happily so, Cubans are very candid about any subject and each one of us was free to open any subject.

3. Routine – Our Undiscovered Cuba tour meant spending an extended amount of time on the bus, or so I thought. In reality, we hit the road every two-three days, which didn’t feel like constant traveling. We made it all the way to Baracoa, in Guantanamo Province (Eastern Cuba), which is when we spent few hours extra on the bus. All other stops were only about two hours away. Either way, this was one price I was willing to pay to see Cuba at its off the beaten path.

Cuba map

Havana -> Santa Clara -> Remedios -> Caibarién -> Camagüey -> Bayamo -> Santiago de Cuba -> Guantanamo -> Baracoa -> Holguín

For me, and everyone else, this was a great opportunity to see more of Cuba: the varied nature, the Cuban cows, the desert-like area, the lush forests, the steep mountains, the beaches. It was fascinating to see how Cuba changed, each time we left a province and entered another one. From Havana’s faded glamour and vintage cars, all the way to Baracoa’s simplicity and horse and buggies. In fact, it made for a heck of a good time as well. When our bus broke down in the middle of the mountains, we just stocked up on rum, Cuban chocolate and finessed our Cuban rhythms. We also caught up on Cuban cinema.

In regards to the advantages of people-to-people tours, I realized they are hard to materialize in any other type of travel to Cuba.

1. No planning required – Any trip one takes usually requires extensive research and planning, and most times, plenty of headaches. InsightCuba took care of all the necessary paperwork: visa, license and charter plane arrangements, as well as providing an incredible itinerary that would take us through Cuba’s hidden gems.

2. Instant access to limited communities – InsightCuba provided access to communities we wouldn’t have otherwise had the opportunity to see, including notable people in the Cuban society. All this contributed to a genuine experience of not only touring Cuba, but also learning about its society, right from the source. The arts & culture aspect was also of top-notch quality, allowing us to meet and witness Cuba’s most talented artists, dancers and musicians.

3. Paid meals–I am not talking about the all-inclusive, lounge around the pool, type of meals. I’m talking about having lunch with local, far-fetched communities, in lovely paladares, in rustic, lush surroundings, and in artists’ homes. Most of our meals were included and planned for, and so, the pressure of figuring out where to eat next was not an issue.

4. A Cuban guide – Apart from the insightCuba tour leader, we had our own Cuban guide for the entire 13 days, as well as local Cuban guides in some of the other towns. Our Cuban guide was not only invaluable in teaching us about Cuba’s tormented past, but also in answering our never-ending fury of questions, in a very forthright manner.

5. Unexpected surprises – There’s an indescribable feeling when a convertible 1922 Ford is waiting outside the restaurant you just had dinner at, to take you back to the hotel, in style; this – along with having our own bicitaxis to drive us around the smaller towns – were delicious treats along the way that we hadn’t expected.


Sure, on my own, I could have woken up at ten, lounged by the beach for half a day, explored Havana, the Cayos and Varadero, where most tourists go, and meet whomever I wanted to meet. Most probably other Europeans and few Cubans.

Instead, I preferred to awake by seven at the latest, run around all day, risk sunburn in 90F at 2PM, but meet real Cubans, and see the real Cuba. Never in a million solo trips would I have had instant access – as an American, mind you – to discussing the past and future state of Cuba with its very own Cuban Ambassador, to visiting the best music and ballet schools that Cuba has to offer, to exclusive dance and music displays, to artists communities, to populations far fetched in the forests, to Cuba’s first entrepreneurs, to personally meeting Cuba’s last remaining music legend.

It was an honor to visit people’s homes – the now famous casas particulares – and dine along with them. I was utterly exhausted by the end, but I wouldn’t change a thing.

Making 20 American new friends, and about the same amount in Cuba was an experience I would repeat anytime. There’s an indescribable feeling of waking up to several emails from Cuba, especially knowing how scarce and slow Internet is there. As for not having to plan anything … I didn’t mind it one bit.

So, what are you waiting for? It’s only 90 miles to Cuba …

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  • I remember the long queue for passport control and feeling a little nervous in case they asked me lots of difficult questions, luckily they didn’t!

    • monicasuma

      Haha. Yes, me too. I had all this paperwork with me, but a big smile too. She was like, take out your hat, so I knew I have to be serious! 🙂

  • Mary Anne Been

    I want to go there! Is it as romantic as it seems?

    • monicasuma

      Oh yes. It really is. And also, the stilness of it all, things move at a slower pace, people smile more, rush less, they enjoy whatever it is they are doing, music is everywhere. There is definitely a lot of romance everywhere. A lot of life lessons to learn from Cuba.

  • @mrsoaroundworld

    I am so happy that US citizens are allowed to go now – I didn’t know how it works, but you made it very clear. Looking forward to next instalments!

    • monicasuma

      Thank you, Mrs O!

  • Lucy Dodsworth

    Really interesting – being from the UK I’d never really thought about how Americans would be able to visit Cuba, it’s great that there is now a legal way to do it.

    • monicasuma

      I know what you mean. Theoretically, me either. But as a dual citizen, it’s something that concerned me directly.

  • Lazy Travelers

    ive always wanted to travel to cuba, and im so glad that there’s now a way to do it! so glad to hear that the group experience was pleasant for you too, as we’d be hesitant to do a trip like that. will have to look into this… xo! the wino

    • monicasuma

      I was hesitant as well, that’s why it was all for the better, an even bigger surprise it was such an incredible experience!

  • Catherine Sweeney

    A friend of mine went on an educational tour to Cuba a couple of years ago — don’t know if it was with Insight Cuba or not. She and her family had a great time and learned so much. I’d love to go there. I’ve never been much of a tour group person, but seems that it would be a great way to see Cuba, especially for the first time.

    • monicasuma

      Well, true, I’m not a bg tour group person either, but given the limited options I went. And it was, as you said, a learning experience, on top of a travel one.

  • dewtraveller

    I didn’t know that Americans could not travel to Cuba. This must certainly be a very exciting and meaningful trip for you. I’m not so much into group trips but I do allow exceptions, and this one looks like a wonderful exception!

    • monicasuma

      It was, it truly was a great experience!

  • lola

    let’s just start with a hotpink passport stamp. one of the millions of reasons i NEED to go to Cuba.

    • monicasuma

      Haha, yes. I told you Lola, all these posts are special dedication for you 🙂 I have more pink coming up. Oh, you’ll love it!

  • Maybe it’s because of mambo, or Cuban coffee I had in Miami, or a book I read about the daily lives of people in Havana, or maybe because I’m curious about Cuban Spanish, but I know I have to go to Cuba at some point. Really glad to see the restrictions loosen and that there are now more (legal) ways for Americans to visit. Anyway, I enjoyed your FB updates from the trip and this post. It’s like walking through the terminal with you (loved the part about trying Spanish with the officer. Don’t you just HATE it when they switch to English?). Good stuff, Monica!

    • monicasuma

      Thank you, Pola, it means a lot!! Glad a I could paint a picture of what was happening during that time.

  • Wow, I have so many questions after reading this! Very well written post, I like your style. I guess I’ll ask two of my questions now. Who took the pics for you since you traveled solo? And How old were the people in your group?

    • monicasuma

      Ask away! I was solo, but with a group. Whoever was with me at the time took the pictures, it was pretty spontaneous, although it may look otherwise. The age range was very wide. I was the youngest, and after that two folks in their forties, and then all much older, up to 80 something even. However all very well traveled, and kept up with the pace, went up and down hundreds of stairs, had incredible travel stories, the age factor didn’t bother me at all. I thought it would, but it didn’t. Weeks after, we still keep in touch, email etc. They’ve all become friends!