This is What Happened on My First Group Tour in Cuba

When you think of a ‘group tour’, what comes to mind? Whatever it is, we’ll be the first to admit that visions of an organized, multi-day group tour, might not paint the most inspiring picture in your head. 

To be honest, before I went on my first group tour to Cuba, I was in the same boat. I couldn’t fathom why someone would pay to travel with a group of strangers. But, like all people who judge a book by its cover, I was wrong and discovered that the idea I had in my head was totally different from the reality.

Travel to: Cuba 

This is my story of what happened on my first group tour in Cuba. Sure I had technically travelled in a group before with my family and friends, but I knew from the moment I hit the ‘book now’ button that this would be a completely different travel experience. 

First Group Tour in Cuba

Me (left) and a few travellers on my tour to Cuba

Booking my first group tour

Fast forward to February 2018, just three months after I had booked my first group tour to Cuba. I was still feeling slightly nervous about it all. Thinking to myself, “Did I make a mistake?” or “Should I have waited until one of my friends was free to travel with me?” rested on my mind. 

Of course, as you may have guessed by now, the answer to all of the questions was no. I didn’t make a mistake at all. And, above all else, I did end up getting a few decent photos that I have now printed, framed and mailed to my favourite celebrities. But enough about the photo opportunities, let’s chat about the incredible tour I went on and the amazing people I toured across Cuba with and what it was really like.  

walking in cuba

A few of the ‘strangers’ who became my friends

What actually happened on tour in Cuba

Let me start off my talking about my new found, touring friends. If you’ve ever been on a tour before you know just how nerve-wracking it can be to meet them for the very first time, and that was no different for me.The lot of us, 16 strangers-turned-travel-buddies in total, met in Havana where we were briefed on what would happen on the tour. Our group were a diverse mix of travellers – a few were around my age (mid-20s) and few more seasoned individuals from Europe and Australia, and myself, the lone Canadian. On my first night, I even I learnt that one of my new friends was a badass research scientist working towards curing malaria! Cool, right?

I was initially terrified by the thought of spending the next 8 days with a group of people I’d never met, but after a relaxing night of food, more food, a walk and a long shared quest to find a place to salsa dance, we returned to our casa’s (a family-run style of accommodation hosted in a private house) and called it a night because in a few short hours the adventure together would really begin. 

Authors note: For American travellers, there are 12 categories of authorized travel that will allow you to visit Cuba including, journalistic activity and family projects. However, depending on the current administration, regulations can change without notice but a people-to-people tour remains the safest option.

Our diverse, lovely and friendly tour group in the Cuban countryside

We travelled from the bustling city centre of Havana to the lush valley of Vinales, to the colourful colonial town of Trinidad via the equally stunning city of Cienfuegos (literal translation, a hundred fires), back to Havana via Santa Clara.

Each morning we were greeted with a delicious homemade breakfast in our casa’s. Fresh fruits, fresh juice, bread and of course, huevos (eggs) made to order. Every day after breakfast we were off again exploring all of the beauty that Cuba has to offer. From its rich and intricate history to its stunning natural landscapes, there was a photo-worthy moment at every stop. 

There were things that I had been dreaming about doing that I finally got to cross off my bucket list while on this tour, as well as things I didn’t even know I would want on my list that I ended up loving.

Horseback riding in Cuba

Horseback riding through the Viñales Valley

My tour group and I did everything from trekking through the Viñales Valley, horseback riding as the sun set off in the distance, swimming in the infamous Bay of Pigs and more. One of the more memorable moments was during our horseback experience involved two of our touring friends suddenly falling ill. Unfortunately, we had to end the experience earlier than expected, but our friendly local guide essentially saved the day. He invited us into his home, introduced us to his family (away from the stables) and made us feel comfortable enough to sit and rest while we waited for a cab to help our unwell friends head home. This small act of kindness spoke volumes about the kindness of the Cuban people, and was just one of the many ways we were always made to feel welcome – no matter how ill our friends might have been! 

The entire experience was unfiltered, extremely informative and eye-opening about what life in Cuba is really like beyond all of the vintage cars and old-school architecture. As for the group, we may not have been the same ages, or from the same cultural backgrounds but we got to experience this tour together which formed instant bonds over our new shared memories. 

One of my favourite moments (admittedly, a little narcissistic of me) was when my new friend, Jade, and my tour guide organized a surprise birthday for me. Never in my wildest dreams did I expect my two-day-old friends to help celebrate my birthday as if we’d known each other a lifetime. I was overwhelmed by their kindness (and the cake).


The art of cigar rolling: one of the many local experiences in Cuba

So, why travel to Cuba? 

Cuba wasn’t always on my bucket list. I mean, it was there, but it wasn’t a top priority considering I’m a lady with only so many vacation days and so little time. But like all good things in life, once I got hooked on the idea, I couldn’t shake it. There’s a certain magic about Cuba that draws you in. Maybe it’s the unique history or the sensation of being frozen in time, dripping in a nostalgia you can’t enjoy anywhere else. Maybe, it’s a combination of both.

Whatever it is, all I knew was that I had to visit, and no matter what kind of traveller you are, you’re going to love Cuba. Live music at every turn, fresh fruits everywhere you go and the lack of advertisement anywhere is a refreshing break from the typical consumerist lifestyle led in most other parts of the world. 

driving in Cuba

You get the feeling that you’re travelling back in time to another world, but at the same time, Cuba is very much still a developing country. You can’t drink the tap water (or brush your teeth with it either – I was sick on the first night doing this). Nor can you flush toilet paper or easily access the internet. But there are impressive gems hidden in the midst of its weaknesses, for example, Cuba is home to one of the best healthcare systems in the world! It was these conflicting realities that made me eager to cross Cuba off my bucket list. That, and the vintage cars, too. 

Why go touring in Cuba?

Cuba was one place that I knew I wanted to go on tour. But travellers join a group tour for a variety of reasons; sometimes for safety, educational reasons or simply because they didn’t want to fuss about the particulars and just wanted to pay a cost and start the countdown – which is exactly what I did. I wanted to explore as much of Cuba as I could while not having to worry about the day-to-day, especially in a destination where I didn’t speak the language or have easy access to Google. I just wanted to book my tour, book my flight and be done with it. And I’m glad I did.

hiking in Cuba

I’m 110% certain that if I hadn’t visited Cuba on a group tour, I wouldn’t have enjoyed it as much because my adventure wouldn’t have been as thorough or covered as many places in only 8 days. I can picture myself stressing about finding a way to get from Havana to Viñales to Trinidad to Santa Clara and back to Havana again (which was taken care of by my lovely guide), but imagine trying to do this all without access to the internet!

I wouldn’t have met my new friends and I certainly wouldn’t have learned all of the intricacies of Cuban life without our knowledgeable local guide, Oswaldo who was adamant about showing us ‘the real Cuba’. There was no question that was off limits and no conversation that he refused to address. It was honest, informative and of course, inspiring to hear of his life in Cuba. 

I would have never gone horseback riding at sunset in the stunning valley of Viñales or found one of the best places to sample a freshly rolled Cuban cigar as shown by Omar who showed us how to roll a cigar while smoking a cigar. It was multi-tasking at its best. I may not have known the kindness of the Cuban people or rested my head after a long day at one cosy casa particular after another.


Pictured above: me contemplating moving to Cuba

Touring: expectation vs. reality

Above all of the incredible experiences I had in Cuba and all of the friends I made, the one that I really took away from this entire experience was that there really is a tour for everyone. I realized that what I loved about group tours (aside from making new friends, trying new things and discovering new places) was that I loved learning. I have always been – and will always be – a huge nerd. I love knowing everything there is to know about a certain place, and had I not been on a group tour, there is so much I would have never discovered about the Cuban way of life. 

If you’re still undecided about touring, only you know what’s best for you. I know that the only thing that lets me rest easy at night is knowing I’ve given every experience its fair shot.  That’s why I had to try a group tour and let me tell you, I’m already planning my next one. 

If you’ve experienced a group tour, tell us what it was like? Did it meet your expectations? Did you meet someone special? Tell us what it was like in a comment below and we might feature you in a future article.