Friends and strangers often wonder how I started off solo traveling, as it continuously plays a tremendous role in developing and improving who I am today. I was not born a solo traveler, but looking back, my journey to this point has felt quite natural.
As a kid, my parents would organize family trips, bringing us back to Taiwan and Hong Kong every two or three years, where they’re from. During the years we didn’t return to Asia to visit family, we went to various cities or national parks in the USA, as well as kid-friendly theme parks like Legoland, Disneyland/Disneyworld, and Universal Studios. We went to Europe one year when I was 10 years old, and my mom made me write about my experience afterward, compiling it into a folder of prose and photos. We would also go skiing about three hours away every winter.
That’s how traveling started for me.
Then, at some point, traveling with parents was no longer the cool move. I wanted to travel with friends, so I did. I would be the one wanting to travel, organizing ski trips and hiking trips in college. Only one attempt succeeded, because friends and their parents would cause the trip to fall through. We went skiing one winter though for a few days and it was great.
At the end of college when I accepted my job offer, the company gave me three starting dates. I chose the last one, leaving my summer completely free. I really wanted to go to Europe, and I asked a bunch of college friends to go with me. A lot of people showed interest, but in the end, only two others came.
We did a lot of planning; each of us picked two or three cities we really wanted to visit, and we figured out the best transportation to get to all those cities. It was two and a half weeks of crammed traveling, but it was also the first time I traveled abroad without my parents and what I realized today was the first time I stayed in a hostel. I don’t remember how I learned about hostels, but we perhaps stumbled upon them just from looking around online.
Before taking off, I bought a backpacking backpack. Well, more accurately, my parents brought it home to tell me to use it, but I didn’t want to. I forgot why I was so against this backpack, but in the end I relented and agreed to use it. I’m very happy with that decision, because stairs weren’t a headache and it was easy to move around.
It was a great trip, mostly because we hit up a lot of places and saw a lot. We had a really tight schedule, but we went on walking tours, saw a lot of monuments, sights, buildings, and ate food. It was a fun time.
Before I knew it, the two and a half weeks had passed and I was at the airport saying good-bye to my friend before heading off to Asia, where I would hop from family to family. It wasn’t that eventful though, as a lot of my time was spent waiting for my family members to take me around. At least I ate a load of delicious food.
I then went to Taiwan to teach English for a month, and then I went to Disneyworld with my best friend. By then, my last summer was coming to an end, and my first time traveling abroad without my parents was over.
I went almost a year after that without traveling, and to this day I’m still not sure why that was. I heard about the beauty of Scandinavia and wanted to go, but I was waiting for people to go with me. One day, I mentioned this to my friend who coincidentally also wanted to go, so we, along with another friend, went.
I did all the planning, although I did ask for opinions regarding what they wanted to do. They had no responses, so I chugged along, meticulously planning every day, every city. I had documents containing popular landmarks and sights, directions from the airport to our hostels and Airbnbs, transportation details, free walking tours, well-known food per country and restaurants to eat, and schedules for each city.
Because of the numerous hours spent researching and looking at maps, I knew the cities before I went. Once we hopped on the plane to Europe, it was go, go, go. No logistical problems, no pauses, just execution. Perfect, flawless execution (except for almost getting stranded on a mountain). Fun!
In most of Scandinavia, I was traveling with only one friend. Turns out I didn’t know this friend as well as I thought I did, because he turned out to be very passive aggressive. He also expected that I knew every answer to his question, and he would be annoyed when I didn’t. You’re welcome for me having done all the research, but why is there an expectation that I know everything? I became annoyed at him very quickly, though we maintained the peace between us.
Then, my other friend joined us, and when we were in Amsterdam (yes, Amsterdam is not part of Scandinavia, but neither is Helsinki nor Berlin, both of which we also went to), my friends wanted to go off to alcoholic adventures. As I don’t drink alcohol, I had no plans to do so and I went as scheduled to a free walking tour and walked around the city. I met up with them for dinner afterward, and it was fine.
While I was walking around the great, beautiful city of Amsterdam, I realized if I could lead two guys through a bunch of cities in countries I have never stepped foot in, I could most definitely go on my own. I felt safe and comfortable having a plan. I knew this with conviction.
After the trip was over, I knew I could try solo traveling. The next trip (to Hawaii) didn’t go so smoothly either, as after I booked tickets, I found out none of the three friends I was going with knew how to swim, and I didn’t want to hold them back to wait for me to snorkel, surf, and swim. I was deciding to hop out on the trip last-minute even though I would still have to pay for all the bookings that were already made. I still went.
On top of that, a (now ex-)friend walked out on the rest of us because he was unhappy, unbeknownst to any of us beforehand. Afterward, there was drama because he refused to pay for any of the post-walkout pre-bookings. In the end, finally, this was resolved and he apologized, saying he was going through a rough time due to the passing of his grandfather right before the trip.
Two trips in a row slightly ruined by different “friends”. I really had to get onto solo traveling.
Thankfully, the opportunity came in a few months, when I asked my work manager whether I could work remotely for three weeks. She said no, but she agreed to two weeks.
Before going, I again meticulously planned all the sights, transportation, accommodation. But this time, a friend who was coming also wanted to plan, but he was basically planning what I had already planned, which was a lot of wasted time.
I traveled in Europe with my friends over Christmas and New Years for two weeks, and then they left to go back to work while I worked remotely. This was the first time I had a taste of solo traveling, and it was great. I was at ease because all the places I went I knew were safe, and I had done a lot of research and planning, which made me feel comfortable. A plan gave me peace of mind. I really enjoyed the trip because it was different, but it was also lonely. I went for days without having actual conversations with people, and I didn’t really understand what I had previously heard about solo traveling, about meeting people while traveling. That didn’t happen to me, not for that trip.
I wasn’t sure how to solve that problem, but it was very liberating to be able to do what I wanted to do, whenever I wanted to do it. I didn’t need to consider anyone else, I could eat wherever I wanted (or not eat), and I could sit down to rest without fearing I was delaying or making others wait. I didn’t have to wait for people to pack, to finish showering. I wasn’t woken up by my travel companions’ alarm clocks, and I could wake up five minutes before I had to leave to catch a plane, train, or bus without padding extra time for waking others up. I was in charge of my own life and my own travels, and I did not need to consider other people or compromise.
I returned from that trip very happy that I felt comfortable solo traveling, because that gave me a lot of freedom. Not just the freedom during my travels, but the freedom to go anywhere in the world without being bothered by whether others would accompany me. I could figure out where I want to go, book a ticket, plan, and go.
I did exactly that a few months later on another trip to Europe, which was after an enjoyable trip with a friend to the US east coast. I went volunteering in Europe for a week and met awesome people, and then I train’d around Europe, visiting random cities. I picked those cities and countries because I knew they would be different than the ones I had been to before, and I did see a lot of new scenery and nature.
I really wanted to meet more people though, as I still didn’t really understand how travelers meet each other. I was staying in hostels but they weren’t super social (or maybe I wasn’t). I asked the few friends I knew who solo traveled how they meet people while traveling, and the most common answer I received was bars. I don’t drink so this wasn’t going to be my way. I let the problem brew in the back on my mind.
It was still a relaxing and pleasant trip, and a few months later, I moved across the US to NYC.
Around this time, I realized through meeting people at the Meetup group I was really involved in back in California that I really like talking to travelers. I had a fire for traveling, and talking about traveling made me excited.
Because I was moving to a new place, I had to make new friends. I had heard about Couchsurfing for a really long time but was always suspicious of free housing; clearly, I did not know the cultural exchange idea behind the platform at the time. However, more and more people told me that they use it just to meet people without staying with others, so after moving to NYC, I started finding people to hang out with through Couchsurfing.
Naturally, because I did, I also asked about and heard a variety of stories from people who actually stayed and hosted people. I decided to give hosting a try, and after a month of hosting, I had my first staying experience. It was amazing.
I was quite pleased with the Couchsurfing platform, and a few months later, I had the opportunity to travel long-term. Before I left the US, I made up my mind to use Couchsurfing as much as I could.
I did, and I met amazing people with amazing stories and amazing lives. It changed the way and purpose I travel, and it was the answer to the problems I was trying to solve: meeting people while traveling. There was, of course, the added bonuses of getting to know the place through the eyes of a local, having a personal tour guide and conversations, and a free place to stay.
My traveling transformed from sight-seeing to meeting people. That’s the purpose for my travels now: getting local perspectives, meeting people I otherwise probably wouldn’t get to meet, having new experiences. It’s no longer about seeing sights, although I still love free-walking tours because I want to learn about the history physically right in front of me. Traveling in this manner is so much more meaningful, and I get a lot more out of it. I learn and grow more, as looking at buildings and landmarks really does not induce any sort of personal development.
I love solo traveling because of the freedom. Freedom to do what I want, whenever I want, with whoever I want. Freedom to go anywhere in the world, regardless of who’s available to join. The freedom mindset is great in everyday regular life too, because if there’s an event I want to go to, I will go regardless of whether anyone can come with me.
Incidentally, I have traveled with quite a few people from Couchsurfing for road trips in other countries as well as my own. Because Couchsurfers mostly have the same mindset, we all get along well and they’re easy to travel with. On these trips though, I often asked myself how a moment would be different had I been alone, and more often than not, this happened when I was waiting for people or had to compromise.
But, as time would have it, my perspective changed over time. I met a Couchsurfer who became an awesome road trip buddy, and ever since I met him, I haven’t done a road trip without him (until he had to move back to his own country, far away from here). About half a year ago after a trip with him, I realized that traveling with him resulted in the best of solo traveling and the best of traveling with others. We are both amazing flexible, enjoy the same activities, prioritize hanging out with our Couchsurfing hosts and meeting other Couchsurfers, like trying different foods and eat everything, and we get along really well just in general. I do not need to compromise my needs and wants, and he does not either. But, when problems arise, there’s another person to help solve them, and best of all, there’s companionship all the time. I was really sad when I went on my first road trip after he left the US. Traveling with him was better than traveling without him.
After this realization, I thought back and saw that I had traveled with another Couchsurfer with whom I did not have to compromise. I had for a while been riding the best of solo and traveling with others, I just did not know it.
One aspect of traveling with others I have not been able to reconcile yet is the dynamic when meeting new people. I like meeting in small groups of people, often just with one or two others, but when my friend and I already know each other, the dynamic is different. It probably depends on which friend I’m with as well.
I constantly ask myself the question when I choose to travel with people now: is having this other person/people with me better than going solo? I came to recognize that making small sacrifices on my trip here and there is acceptable as long as for the most part, I get to do what I want and I get to concentrate on meeting people.
It seems that perhaps I went in a full circle — traveling with others to solo traveling, and back to traveling with others. But I didn’t. I reached a new dimension, one where not only do I completely understand the benefits and downsides of both worlds, I have experienced getting the best of both worlds. Solo traveling is always my first choice, unless I know (or have a strong feeling that) the person or people joining me will positively impact my trip, that I would rather make small sacrifices to enjoy their company.
The transformation from traveling with parents, with friends, and finally solo has been an amazing ride, and as time goes on, my travel style and revelations continue to change. I can’t wait to experience the gradual yet apparent evolvement of my travel style, and it has been a wonderful ride up to now.
