The Art of Traveling Solo

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“Not all those who wander are lost.” -JRR Tolkien

The famous English author, J.R.R. Tolkien, once wrote in his poem “All that is gold does not glitter” a line that should be noted for its’ truth and its’ profundity. The 2nd line of the poem states, “Not all those who wander are lost.” This is a fitting statement for those of us travelers who have stepped foot in another city or country being completely on our own. It’s not something that can be easily done and requires a bit of mental fortitude to be able to enjoy it despite the inherent challenges.

While most travelers like to go from place to place in packs, big groups, or in guided tours, I believe that it is necessary to try out traveling alone especially if you have prior experience in traveling to other cities and countries. Once you are comfortable with the art of traveling itself, I think it’s a good idea to challenge yourself by traveling alone. I won’t choose to judge you if you decide to never try it by I respect any fellow traveler more when they tell me that they have been by themselves in a new country for days, weeks, months, and even years at a time.

In order to travel alone successfully, I would recommend that a person be able to adapt or inherently have a few traits or characteristics that will put them more at ease with the idea. First, you have to be comfortable being alone. You have to be able to embrace the solitude of your thoughts and to be more observant of the world. This is a hard thing to accomplish for strictly extroverted people who thrive off of the energy of being around others. However, if you’re a strict introvert or fall somewhere in the middle of those two broad categories like myself, then you won’t find traveling solo as hard as pure extroverts. Sometimes, you will have to be alone in a restaurant, in a museum, or in your train/plane/taxi.

I think there’s a benefit to this because then you’re more likely to focus on the place you’re traveling to and be able to better absorb the culture, customs, and especially the food/drinks of the new place you’re traveling to. When you’re with your friends and family on a trip, you’re often wrapped up in what they’re thinking, what you’re going to do with them for the day, if they’re having a good time or not, etc. With friends and family, you’re in a mini-bubble that’s hard to break out of. When you’re traveling with another person or a group in general, you’re less likely to appreciate other aspects of the trip. How can you focus on the sheer beauty of the Coliseum in Rome, Italy when your close friend is trying to discuss the latest Game of Thrones episode with you?

Some critics of traveling solo also forget about the fact that you will still meet people during your travels to new places. You’ll only truly be alone if you never open your mouth and be social. It’s easier now than ever to connect with new people and make new friends due to the wonders of the Internet. Due to the popularity of websites like AirBNB, Couchsurfing, and the ubiquitous amount of hostels in every part of the globe, even if you travel alone for an extended period of time, it’s still easy to meet people due to the sharing economy’s emphasis on affordable, shared living spaces.

I also couldn’t forget the sheer amount of other opportunities to have language exchanges, expat gatherings, and to just make the effort to open your mouth to someone and start a conversation. I find that it’s easier to meet people on the road than it is when I’m at home because they’re curious about where you’re from, how long you have been traveling for, and what you are doing in their country, etc. and you’ll also be curious about the same things.

During my recent trip to Santa Marta, which was done solo, I was able to befriend my kind AirBNB host from Bogota, hang out with the locals at a bar, and practice my beginner Portuguese with a Brazilian woman from Rio de Janeiro. When you’re traveling alone, you really have to put yourself out there and be more social. That’s not easy for a lot of people but it’s important to try it at least once. If you have any kind of social anxiety or shyness, you’ll be able to overcome it more and more due to solo travels.

Traveling alone is something that you have to ease into over time. I think it’s wise to start with a day trip to a nearby city where you don’t know anyone and then eventually work your way up to visiting a new country by yourself for a few days or a week. Personally, the longest that I’ve traveled by myself for has been about two weeks. I’d like to eventually reach that level of a month or more on the road without anyone holding my hand. Traveling alone forces you out of your comfort zone and mentally challenges you. You have to navigate a new city and country, practice the language by yourself, and be able to handle flights, trains, and buses without the guidance of others.

While this is not easy and takes practice, you’ll feel more confident and sure of yourself as a result. The times where you could have been taking selfies with your friends or partying until the wee hours of the morning are instead focused on having a nice coffee by the river or taking your time in an art museum by going through the galleries at your own pace. Traveling solo is a good time to be selfish as you can set your schedule, your own destinations, and decide where you want to go and when you want to go. There’s nobody holding you back and that’s quite liberating. I often get a feeling of true freedom while traveling alone that’s not easily replicated.

Even if there was no one else physically with me, I have nice memories of my past solo travels. The moment when I woke up on my train to Krakow, Poland in the early morning to open my window to see fresh snow on the ground and the sun rising as we entered the train station. The feeling of pure relaxation as I enjoyed a nice mid-day cappuccino with a view of the Prague skyline in the Czech Republic, and the absolute quiet I felt as I sat on the beach in Parque Tayrona, Colombia and heard nothing but the soft, sea breeze and the waves splashing against my feet. These are the memories that I will cherish and never forget. That is why I enjoy the art of solo traveling.

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The Life and Times of Ben Weinberg
The Life and Times of Ben Weinberg

Written by The Life and Times of Ben Weinberg

English Teacher, Entrepreneur, World Traveler, and Writer from New York.

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