Lonescapade: My First Solo Trip

A little over two years ago, as I went through a transitional period in my life- getting my first adult job and questioning the things I wanted- I took a trip to Charleston, South Carolina. The place is not hugely significant nor the means of getting there, as Charleston is a mere four hour drive from my home in Atlanta, but it was the first time I went on a trip alone for pleasure.

I had scheduled some time off work and I remember my coworkers asking how I planned to spend my long weekend. It felt strange and a little uncomfortable trying to explain that I just wanted to get away for a few days… on my own. As if I needed an explanation for my solo hiatus, I offered some kind of follow-up like, “I’m hoping to get a lot of writing done”.

Maybe I did think it would be a working trip initially. My laptop was packed and I even sat in front of it for about ten minutes in my hotel room. However, it ended up being an adventure that awakened me to how I like to travel and explore- on foot with a loose schedule, letting curiosity guide me.

The Ansonborough Inn, where I stayed, offered the perfect setting for my retreat. Dating back to the 1700s, the inn has the quintessential historic Charleston feel- meaning, I felt like I was staying in a refurbished pirate ship. Wood beams are exposed through the lobby and antique paintings of the ships at sea adorn the walls. It certainly struck a chord with my aesthetic. Many of the guest rooms are uniquely laid out. Mine had a wall of windows, covered with wooden shutters.

While the inn suited me well, I distinctly remember a point where my solo-ness made me uncomfortable. The inn offered a free wine and cheese social and my response was, “Free wine? Show me the way!” The tables were mostly filled with families eating together and to avoid feeling awkward as the only person eating alone, I took my wine and cheese to my room.

The dining experience is definitely a hurdle for solo travelers. You have to accept that you belong in a public dining facility just as you are, without the fear of being scorned or gawked at. Because I was still getting used to doing things alone during this point in my life, I mostly ate on the go- especially for dinner. It took some time for me to gain the confidence and face the fact that there is nothing wrong with eating at a restaurant alone- I have to eat, that family has to eat, that couple has to eat. It doesn’t matter.

Beyond getting over eating alone, the rest of my trip had almost no snags. Once I parked at the inn, I didn’t get into my car for the next two days. I set out to explore Charleston on foot and discovered that there is something to savor in wandering and letting curiosity guide me as I discovered a new place. I walked about ten miles a day, seeing the historic sites, exploring centuries-old neighborhoods, eating and shopping. I did everything I wanted over that weekend without compromise and through my own independence.

Traveling alone teaches us something valuable- we can rely on ourselves. Self-reliance is like a muscle. We have to show it what it is capable of and that might take some training. Before I went on this solo trip, I relied on someone else to make plans or to validate the plans that I made, but traveling to Charleston, I was responsible for all planning and arrangements. It showed me that I could do it.

My first solo trip took me down a rabbit hole of self-reliance and following my curiosity. Now, I regularly seek out places I’ve never been without concern for whether I am alone or not. Even if it’s just a park near my home that I have not visited before. My self-reliance has grown and I love this aspect of my life. Being able to do things alone has given me the freedom to live my best life.