Why Everyone Should Travel Alone at Least Once
What Solo Travel Teaches You About Yourself
There’s something deeply transformative about being alone in a foreign place.
No plans. No familiar faces. No safety net. Just you figuring it out as you go.
For most of my life, I’ve usually traveled with family or friends. Those trips are always super fun, full of laughter and shared memories. But early last year, I felt a growing curiosity about what it would be like to venture out on my own.
So I decided to try something different: I booked a ticket to Portugal, alone.
No travel companion. No real plan. Just a sense that it was something I needed to do.
That trip was one of the best things I ever did.
As you read this, I’m probably sitting somewhere in Kyoto or Takayama, halfway through a three-week solo trip across Japan — my longest one yet. And just like last year, I’m equal parts excited, grateful, and slightly terrified.
Because solo travel has a way of stripping you down to your essentials.
It’s uncomfortable. It’s beautiful. And it teaches you more about yourself than almost anything else.
My First Solo Trip: Portugal
The days leading up to my Portugal trip were filled with nervous excitement.
Sitting alone on the plane, I felt a mix of anxiety and anticipation. What would it be like to navigate a new city entirely on my own? How would I handle the inevitable moments of loneliness?
When I landed in Porto, I felt a bit lost. I struggled to find my hostel, and when I finally checked in, I was somewhat overwhelmed by the realization that I was truly on my own.
But that feeling didn’t last long. On my very first night, I met other travelers and hostel staff who quickly became my companions. We explored the city together, stayed up late, and shared stories over drinks. By the end of the night, I went to bed thinking, “This is already amazing.”
It was a reminder that the things we fear often turn out to be far less scary than we imagine. That nervousness I felt? It pushed me out of my comfort zone and led to amazing connections.
Why Solo Travel is Worth It
Unmatched Freedom
Solo travel offers a level of freedom that’s hard to replicate.
Your schedule is entirely your own. There’s no one to wait for. No one to convince. No “where do you want to eat?” debates.
You can wake up at 6 a.m. to catch the sunrise or sleep until noon without guilt.
You can extend your stay in a city you fall in love with or leave one that doesn’t feel right.
In Porto last year, I originally booked three nights. By day two, I knew I wanted more. I extended another night and spent the extra day having a hostel family dinner, eating pastéis de nata, watching the sunset from the Luís I Bridge and finishing the night with a city pub crawl.
It was one of those perfect, unplanned moments that only happen when your time belongs entirely to you.
That kind of freedom builds a powerful muscle: the ability to make decisions and own them.
When things go well, you take credit. When they don’t, there’s no one to blame but yourself. You realize how much of life is just a series of choices, and that you’re capable of making them on your own.
Most people underestimate how rare that feeling is.
The Fear That Disappears
Before I left for Portugal, I was nervous about being lonely.
What if I didn’t meet anyone? What if I didn’t know what to do?
But the reality of solo travel is the opposite: it’s almost impossible not to meet people.
The moment you step into a hostel, join a walking tour, or sit alone at a bar, you’re instantly more approachable.
Locals and travelers alike will start conversations with you — because in the end, they want the exact same thing you do: to meet other people and build connections.
I was surprised how many amazing people I got to know last year, and in the end I spent most of my route with people I met on the first days.
The fear of loneliness ironically turned into one of the most social experiences of my life.
The Gift of Time Alone
Even with all the people you meet, solo travel gives you more time alone than you’re probably used to. And even if you are alone most of the time, that doesn’t necessarily make the trip worse.
Because you’ll notice that being alone does not have to mean being lonely. Instead of viewing it as loneliness, think of it as solitude.
And that solitude is where most of the growth happens.
When you’re by yourself in a new environment, you will have space to reflect and rediscover who you truly are: your thoughts, your habits, what actually makes you happy.
There are no expectations. You’re not performing for anyone. You’re just existing.
It’s in those quiet moments — sitting on a park bench, journaling after dinner, or watching the world go by from a train window — that you start to rediscover who you are when nobody’s around to define you.
You realize what you genuinely enjoy versus what you’ve been doing out of habit or expectation. You might discover that you enjoy things you never thought you would or that you’re capable of more than you imagined.
And all these small realizations add up to a deeper understanding of yourself.
There’s a quote I love:
“All of man’s problems stem from his inability to sit quietly in a room alone.” — Blaise Pascal
Solo travel forces you to confront that truth.
To sit with yourself, your thoughts, emotions, and discomfort, until you make peace with them.
And once you do, you carry that calm confidence back home with you.
The Confidence That Compounds
When you travel solo, you’re forced to rely on yourself.
You figure out metros in languages you don’t speak. You navigate confusing streets, misbooked hostels, and late trains. You order food you can’t pronounce.
At first, it’s stressful. But then, you start trusting yourself.
You realize you can adapt. You can improvise. You can handle things.
This self-reliance builds confidence that carries over into every area of life.
When you return home, small challenges no longer feel like a big deal. You stop over-relying on others because you’ve already proven to yourself that you can handle being on your own.
You don’t just come back from a trip with pictures. You come back with proof that you’re capable.
Why You Should Try Solo Travel
If you’ve ever considered solo travel, even once, I encourage you to take the leap. It doesn’t matter where you go or how long you stay—what matters is that you step out of your comfort zone and embrace the adventure.
Whether you meet incredible people or spend time in solitude, you’ll come away with a deeper understanding of yourself and the world around you.
Solo travel isn’t always easy. You’ll feel discomfort, uncertainty, and maybe even fear.
But that’s exactly why it’s worth doing.
You might more about yourself in a few weeks than in years of routine life.
You’ll realize:
Freedom is choosing your own pace.
Growth happens right after fear.
Solitude is a teacher, not a punishment.
Discomfort builds confidence faster than comfort ever could.
Even the worst-case scenario is a win.
Worst case, you come home clearer and prouder. You discover solo travel is not your thing. That clarity beats wondering “what could have been” for the next ten years.
And the best-case scenario? It changes your trajectory.
You make friends you will keep for decades. You fall in love with a city. You learn skills that make you stronger and calmer. You find stories that you will tell forever. You rediscover yourself. You create memories that you’ll never forget. You put places on your mental map that you will want to return to with the people you love, carrying the memory of who you were the first time you stood there alone.
The Paradox That Makes It All Worth It
My birthday last year was in Portugal. I went in ready to be alone. I ended the night at a wine bar with new friends I met along the way, a free cigar from the owner, and a cake I did not expect.
And even if I had been alone, it still would have been special. Either way, I would have remembered it clearly. That is the magic.
And still, this year I feel nervous again. And that’s just part of it.
One of my friends that celebrated with me reminded me of this before Japan (Shoutout to Joab🙂):
“Just think back to when we all met in porto, it was not planned, you had the fear of having a lonely birthday and the exact opposite happened!
And if you need to be alone, life will put you alone but with all the circumstances to get an amazing trip!! So even alone, you’ll be great!!”
And that’s exactly right. No matter what happens, embrace the uncertainty and make the best of each situation.
By the time you read this I’ll probably have already experienced moments of loneliness, but I’ll also have had moments of pure joy and connection. I’ll have met locals and fellow travelers, explored stunning landscapes and temples, and immersed myself in a culture that’s completely different from my own.
I’ll have learned to be more adaptable, more open-minded, and more confident in my ability to navigate the unknown.
And I will be missing my friends and family back home. You know who you are :)
Final Thoughts
If you’ve ever thought about traveling alone, take this as your sign to do it.
Book the flight. Don’t overthink it. The planning, the nerves, the “what ifs” — they all fade the moment you land.
Last year in Portugal, I celebrated my birthday surrounded by amazing people I met just days earlier — eating cake, drinking wine, and laughing in a tiny cellar bar.
This year in Japan, who knows where I’ll be? Walking through Kyoto at night, eating takoyaki, doing a late-night konbini run, singing karaoke with a random stranger, riding a roller coaster at Universal Studios, sharing drinks with locals at an izakaya?
That’s the beauty of it. You never really know. And that’s exactly what makes it special.
Because the real journey isn’t through cities or countries — it’s inward.
Solo travel is just the vehicle.
So if you ever get the chance, take it.
You might discover that being alone was never the point.
It was about learning to come home to yourself.
Thanks for reading.
Safe travels,
— Tobi
💡 Question: Have you experienced solo traveling before?
Loved reading this. Reminds me of my own solo trip eons ago! You’ve planted an idea for a post! Thanks Tobias. New to Substack so the inspiration is perfect! I’ve been to Japan a few times, where are you heading too? Happy to share notes.
You've really encouraged me to try and overcome the fear of travelling alone.