If you know me, you know that one of my passions in life is travel. Travel has always held an enchanting allure for me. Even as a child, I would watch the Travel Channel and dream of visiting the places and having the experiences I saw the hosts of the show enjoying. My parents always talked about their dreams of travel, but they made it to a sad few of their destinations; I decided that I would not allow myself to not reach my destinations. So in my early twenties, I decided to start traveling to my destinations at least once per year; that commitment lasts to this day.
Now, when it comes to travel, I have found that it is often hard to organize and get other humans to commit to adventure. Unfortunately, I have met many people who have not traveled simply because they have been unable to secure friends and family to travel with them. I decided early on that I would not allow myself to be dissuaded from travel if my friends or family could not come with me because of work, money, etc, which is why I have opted to travel alone several times throughout my wanerlusting career.
In fact, as I write this I am on a solo trip through the beautiful country of Greece. As I wander around this historically and culturally rich land on my own, I am reminded of the challenges and discomforts, the opportunities for growth, and the joy that traveling solo can bring. And it is these things I feel compelled to share about with you today.
Pros & Cons of Traveling Solo

Temple of Apollo, Naxos, Greece
Pro – King/Queen of Your Own World
When you travel alone, you are beholden to no one and free to make your own decisions without question or consultation. There is no compromise about what you want to see or do, there is no discussion about if this or that restaurant sounds good for a meal, there is no waiting on someone else to finish getting ready. Rather, you wait only on yourself, you do what you want to do, you go where you want to go, and you eat what you want to eat. Traveling solo may be one of the most independent experiences you may ever have and it is truly liberating!
Con – Lack of Camaraderie
It is liberating to answer to no one, but while traveling solo there are moments where you may wish you had a friend or ally. In uncomfortable situations when you are unsure of what your next move is or you are confused about how to navigate somewhere, you might long for a friend or significant other to be in the situation with you – helping you to figure it out and assuring you that no matter what, you are in it together. It is in these moments of discomfort during solo travel that feelings of loneliness can be overwhelming powerful. The only option you have is to breathe through the discomfort and find a solution on your own.

Palace of Knossos, Heraklion, Crete, Greece
Pro – Learning to Be More Self-Sufficient
In these moments of discomfort while traveling alone, you have no choice but to quickly learn how to problem solve. You are forced to go internal – to think critically, to think logically, and to use your intuition. It is through this process that immense growth occurs. You learn to remain calm in stressful situations, you learn to use your own brain to find the solution, and perhaps most profoundly, you learn to trust and believe in yourself to find a way and be okay.

Filot, Naxos, Greece
Con – Dining Alone
I have heard many solo travelers talk about the awkwardness of going to a restaurant and dining alone.
It can be an experience that makes you feel totally isolated and it can also be more expensive as you do not have the option to share dishes. Here are some tips to make dining alone feel less awkward and actually be enjoyable:
- Bring a book – I always bring a book to restaurants when I am dining alone. Reading can help you to feel more occupied and get you out of your head worrying about what other diners are thinking of you or just how alone you are. Enjoy reading in between bites of food and sips of wine. After awhile, it feels pleasurable to enjoy a meal alone with a good story.
- Save some of your meal for later – I sometimes will eat half my meal at the restaurant and take the other have to-go (it’s called takeaway in Europe) to enjoy for lunch or dinner later on. Especially when I am in an Airbnb and have a means to reheat my dish, saving some of your meal is a great way to save money and time!
- Connect with other diners – I have found that when dining alone, other restaurant guests will strike up conversation with you as they recognize you are alone. This can be a great opportunity for connection and even new friendship! You might even end up moving from your table to theirs to join them in the meal; it has happened to me more than once.
- Reap the pity – When they realize I am traveling solo, some servers at restaurants seem to feel bad for me and thus gift me an extra glass of wine or a dessert on the house. I assure them that I am okay on my own, but I happily accept the complimentary glass or plate!

Solo Dining in Chania, Crete
Pro- See more faster
Traveling solo can often lend itself to seeing more on your itinerary more quickly, at least in my experience. Since you do not have to wait for another human to finish getting ready or coordinate with them in anyway, you are free to zip and skip around your destination and accomplish what you desire. Additionally, as a solo traveler, you are more likely to be let into popular attractions more quickly – it’s sort of like being a single rider at Disneyland.

Parthenon, Athens, Greece
Con- No one to take your photos
In the Instagram age, having your photo taken at beautiful and awe inspiring destinations is a must! But when you are alone, it can be a struggle to get that perfect shot. I typically hang out where I want a photo for a few minutes, identify a friendly looking stranger and ask them to take my photo. Some of my best travel photos have been taken by friendly strangers. However, you can’t expect them to take 20 different shots like you can with your bestie or S.O.

Agios Prokopios Beach, Naxos, Greece
Pro- Meet new friends
There is something magical that happens to humans when traveling – we seem to be more open and ready for new experience and connection. I have made new friends every time I have traveled, especially when I have traveled solo. From meeting a new group of friends on my tour of Italy with whom I still talk to to this day, to encountering my buddy Fabrizio and his family in Paris and going on to stay with him in Amsterdam 2 years later, to connecting with my new friends George and Selma on a SUP adventure in Crete and going to get dinner and drinks with them later on that night, to meeting my new friend Leela who offered me a ride down a mountain in Santorini to escape the sudden rain and then asking me to go wine tasting with her and her sister. It is these serendipitous connections that make a lasting impression and memory that cannot be forgotten.
The connections I have made while traveling have inspired me to be a more open, friendly person in my everyday life and have taught me just how much we as humans are looking for authentic connection through openness and vulnerability. Moving through life with this experienced knowledge is truly life altering.

Partying with new friends at Paradise Beach in Mykonos
Pro – Experience the kindness of strangers
This goes along with meeting new friends. One of the most profound aspects of traveling solo is connecting with strangers and experiencing their kindness. As a solo traveler, you sometimes have no choice but to turn to strangers for support or help, and the responses you may receive can be amazing. I have received so much aid and so many blessings from strangers while traveling solo. It has affirmed my belief in the kindness of strangers and the inherent good that exists in our kind. The kindness I have received from strangers has helped to color my outlook on life.

SUP in Crete with new friends, Chania, Crete
Pro – Learning to make peace with yourself
As you can imagine, traveling solo lends itself to, well, a lot of alone time. It is a “me, myself, and I” situation all around. When you are forced to sit with yourself for such long periods of time a great deal of self-reflection begins to take place. Self-reflection can me immensely uncomfortable and we may start desperately looking for a way to escape it. However, if you can lean into the reflection, you may begin to make peace with yourself in the moment and identify ways you may grow moving forward. At first it feels like a con, but eventually it becomes a pro.

Mykonos Town, Mykonos, Greece
So clearly, traveling solo is complex and evokes so much within us humans. I am a firm believer that everyone should embark on a solo travel adventure at some point in their lives.
Now, as a white man from the US, I enjoy a great deal of privilege in my life and feel comfortable traveling far and wide. I recognize that traveling solo to some destinations is not as accessible for women or people of color due to the inequalities we are currently battling in our world. However, solo travel does not have to be to faraway, exotic destinations; you can travel to a new city within your own country or state! Solo travel can still be a wonderful, growth-filled experience even if it is still within the safety of your own land. For example, if you are an American, maybe try traveling somewhere like New York or San Francisco on your own – same language, same culture, socially liberal, overall safe, but still big and exciting enough to get all the benefits I have mentioned in this article. Additionally, countries like Ireland and Scotland are very safe, open, and friendly to everyone and most people of all stripes say they feel comfortable traveling to these destinations. Go only where you feel comfortable and safe, but do indeed go!
Traveling solo has blessed me with some of the greatest experiences I have had in this lifetime and has cultivated growth within me that I do not believe I would have found anywhere or anyway else. Solo travel is scary, it’s exhilarating, it’s liberating, and it is profound. I hope that you can experience all that traveling solo has in store for you when you answer the call.

Naxos Town, Naxos, Greece