What I Learned From Traveling Alone


Last September I went to Boston for the first time. Prior to this trip, I had never flown by myself and I had never been to a new city by myself.

I was going for a work conference and had the choice to either A) fly in the first day of the conference to meet my boss or B) fly in a day or two before, but be on my own. 

This decision was more than just making an efficient itinerary. This decision was about if I could push myself to be independent and brave in a new city I knew hardly anything about. Typically, I would stay in my comfort zone and fly out when I had less time to be alone. But this was an opportunity to try something new in a big way.

With much hesitation and fear I bought a ticket out a day early to be on my own in Boston. No turning back now!

This was my chance to put myself out there on my own terms. It was the perfect opportunity to explore a city I had never been to and make my own agenda. It was also the perfect opportunity to see if I could handle complete self-reliance, even if just for a day.

It’s now a year later and I’m still shocked I had this experience willingly. Don’t get me wrong – I can generally be a pretty independent person. But I also like to surround myself with people I trust and have no trouble asking them for help. In doing so, I can often get in a rut of not feeling comfortable to do things on my own.

But when those moments creep in, I can look back on my solo day in big ‘ol Boston and think, “Girl, you did that!”

Here’s a few things I learned from that experience. 

You do you

Overall I learned that traveling alone means you can do whatever you want whenever you want without compromising to someone else. Everyone likes to do things their own way and that can get frustrating, especially in tense situations like navigating through a busy airport. But on your own you can do everything your way and don’t have to justify your decisions. Don’t wanna visit another art museum? Don’t. Wanna skip the trendy ice cream shop with a line down the block? Do it.

Be smart though

On the other hand, you’ve gotta be street smart on your own. I found myself watching my back more than usual and made sure to keep close watch on my Google map routes. Follow the route of your Uber or Lyft driver to make sure they’re not going off course. Keep your purse close to your waist. Don’t leave the hotel without a fully charged phone. You know the drill. I figured the safest thing to do in a new, big city was to act like I knew exactly what I was doing and where I was going. Fake it till you make it, right?

Skip the car

Walking or biking is the best way to take in your surroundings. Boston is a walk-friendly city, and I took full advantage. You’ll miss the personality of a new place by looking out the window of a car. Smell the city. Hear the locals. See the details. Boston has history on every corner (literally) and it would be a shame to miss that for the sake of convenience.

Take some ‘me time’

Traveling alone forces you to be your own best friend. If you’re feeling lost or struggling to find a sense of self in our crazy day-to-day lives, travel somewhere by yourself. It doesn’t have to be far, but get out and spend some quality time with you. It’s a great chance to reflect on your life and what you want without interruption from others. It can also open up a new perspective on what you already have. Sometimes a change of scenery is all you need to clear your mind.

Overall, I’m not sure I would book a vacation on my own in the future. I like to share experiences  with others, so on this trip I often found myself wishing my boyfriend or family was with me to share in the beautiful surroundings. But I am proud that I can say I did something I never thought I would. You should give it a try too.

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One thought on “What I Learned From Traveling Alone

  1. I struggle with alone travel. I travel alone for work frequently and have “figured that out”, sort of. My issue is pleasure alone travel. I find that I want to share my experiences with someone…not just telling the tale, but reminisce. That’s when I feel the most lonely. Like you, I just need to push myself out of my comfort zone. Great post! Cheers,

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