How a Group Trip Turned into a Solo Adventure
So, what do you do when you only have a few specific dates, when you don’t have the time (or energy) to plan everything, or when you simply don’t feel like organizing anything and just want to enjoy yourself?
Let me give you an example: my three trips to Cuba. Each one was a completely different experience.
This island stole my heart in every way.
Keep reading, because what comes next might make you rethink your approach to travel—or even take steps you hadn’t considered before.
The Unexpected Truth About Group Travel — Lessons from My First Cuba Trip
Let me set the scene: After returning from my first trip to Cuba, I stumbled upon an online platform that offered unique experiences with locals. But here’s the catch—these weren’t your typical, run-of-the-mill experiences. They had a sort of alternative, offbeat vibe. On this platform, I found a whole array of activities that I wish I could’ve experienced during my first trip to the island. Unfortunately, I missed out on them due to my lack of knowledge at the time.
Another thing to consider about my first Cuba trip: I was planning something long-term, and I didn’t have anyone close to me who could join in at the same time. So, for the sake of splitting costs (I mean, who doesn’t want to save a little?), I decided to jump into an online forum to find a group of like-minded travelers who were also heading to Cuba around the same time.
I wouldn’t necessarily call it a mistake, but let’s just say… it didn’t exactly go as planned. The idea was to organize everything ourselves, gathering information from all sorts of online sources.
Now, I’m the kind of person who has no issue talking to strangers and loves meeting people from all walks of life. I thrive on connecting with new faces and hearing their stories. But my friends, there’s one important lesson I learned the hard way: you really need to know who you’re traveling with. This is not something to take lightly.
Keep reading, because what follows might have you thinking twice about your own group travel adventures, or at least help you choose your travel companions more wisely.
La Habana: @aarpitmehrotra @edinchavez
Planning My Cuba Trip – The Group Travel Experience
They say that when you plan a trip, you’re already traveling twice—once when you organize it, and then when you actually experience it. Well, when I was preparing my Cuba trip, I was very much immersed in that first “trip” of organizing, especially considering that I was traveling with a group of strangers. It was crucial for me to get to know who I would be sharing this adventure with, so I followed all the necessary protocols (yes, that word we love to overuse now).
During this phase, I was genuinely enjoying the process. We had regular phone calls within our group, and those of us from Madrid even met up for drinks to break the ice. Eventually, we created a WhatsApp group where things began to shift, and the differences between our travel styles started to emerge.
Let me tell you, this group chat was a rollercoaster. People formed couples, there were debates, and at first, it was all sunshine and rainbows. Isn’t that always the way when you’re starting something new? Everyone gets along in the beginning, right? I remember for those of us flying from Madrid, our flight to Havana had a late-night layover in Amsterdam. Since it was just a few hours and the hotel prices were outrageously expensive, we decided to head out into the city, skip booking accommodation, and return to the airport for our next flight. Now, let me tell you: exploring the coffee shop scene in Amsterdam after pulling an all-nighter was an experience in itself. And that’s coming from someone who doesn’t smoke. The fog of those places was intense! Safe to say, that flight to Havana was something else.
La Habana: @jochyamp
The Reality of Traveling with Strangers
But here’s the thing, looking back—being in a group like that means you really have to be on the same page. You need to connect on a deeper level, at least in terms of travel preferences and lifestyle. Can this happen? Yes, it absolutely can. I’ve seen travel agencies abroad that organize trips around very specific interests, like visiting local communities or artisan workshops. It’s an interesting concept that I’ll save for another post because I could really dive deep into that idea.
Back to my first trip to Cuba, though, at the start, everything was golden. But as the days passed, things started to unravel.
For example, I had to endure a few typical touristy activities—think “mojitos at the Hotel Nacional in Havana” or a night out at Mio y Tuyo, a spot that was completely out of my element when it comes to nightlife. But hey, life’s about embracing every experience, right? I ended up seeing a side of Cuba that I probably would never have encountered on my own. To give you a better idea, imagine being taken to an ultra-exclusive, VIP-reserved venue when your thing is exactly the opposite—alternative, off-the-beaten-path places. It’s like that, but you learn from it.
From Group Travel to Solo Adventure
Thank goodness this trip was long. If I remember correctly, I spent around eight days with the group. During many of those days, although I was still with them, I ended up doing my own thing, taking advantage of shared transport and accommodation to save a bit. But hey, not everything was bad. Honestly. Maybe I’m a bit particular, I don’t know, but I probably am.
So, when did the magic happen on this trip? It was the moment I decided to break away from the group and go solo. After visiting Cienfuegos and Trinidad, where I met an incredible guy in the latter, I decided to spend three days in Cayo Coco to recharge and relax before continuing on to Santiago de Cuba. That decision to go my own way was absolutely the right one. (In case you’re wondering, I left the guy in Trinidad and continued solo, though I was never really alone.) Cuba turned out to be one of the most unforgettable trips of my life, and I’ll dive into more details in another post.
Cuba is the kind of island where, even when you’re traveling solo, the warmth of the Cuban people ensures you’ll never truly be alone. In fact, there were moments when I actually missed real solitude. One particular memory that stands out is my visit to Santa Clara—Mejunje de Silveiro and Parque Leoncio Leal truly deserve their own chapter. Those who know, know!
The Real Cuba: My Journey Beyond the Group
Breaking away from the group in Cuba was a pivotal moment for me. It was then that I truly discovered the soul of the island—its authentic energy, the beauty of its culture, and the warmth of its people. Traveling with others can be rewarding, but it’s equally important to connect with those who share your travel vision. And when that doesn’t align, sometimes going solo is the key to unlocking the real essence of a place.
It’s a lesson I’ll carry with me: Whether with the right company or alone, it’s the freedom to follow your own path that allows you to experience the true spirit of a destination.
I’d love to hear your thoughts. Do you believe the right travel companions make all the difference, or do you prefer the adventure of going solo?
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