My First Solo Trip Was a Failure; Here's How to Make Yours a Success

(Image:  Pixabay )

(Image: Pixabay)

One human quality that is probably universally appreciated by others is the ability to admit when a mistake has been made. As I get older and as hindsight continues to provide me with 20/20 vision, I find this ability comes more and more naturally to me. And that's why I have no problem admitting to you that my first attempt at solo travel was not exactly a success.

Truth be told, you could not be faulted for labeling it an all-out failure really. It was in early January 2015 that I decided I would take a trip to Vermont and stay at a cabin in the woods. Without a detailed plan or a thought for who might make the trip with me, I booked the cabin through Airbnb. Two months later, the only potential traveling companion I'd had in mind was unable to join me and I set out by my lonesome for a long drive through Canada that would eventually get me to New England.

If that setup sounds at all familiar, it's most likely because you've read my previous post about this trip, which is called "That Time I Climbed a Mountain Alone." But if we're adhering to my stated goal of readily admitting mistakes, I can admit that that post doesn't provide the full picture of my solo travel experience — it kind of skates around the topic, in fact, willing neither to recommend nor condemn.

These days, I'm undoubtedly a fan of traveling alone. While personal safety must be kept in mind, venturing out on your own provides an incomparable way not only to learn things about a new place but also to learn new things about yourself, such as how well you can intermingle with strangers and how you'll react when faced with inevitable unforeseen circumstances.

What I'm not a fan of is the way I conducted myself during my first solo adventure. Why is that, you ask? Well, I think the only worthwhile conversation I had with anyone while on that three-day excursion back in March 2015 was with my Airbnb host. While in Vermont, I visited the University of Vermont in Burlington, Ben & Jerry's Waterbury FactoryHarpoon Brewery, went for a hike up Mount Ascutney, and even went over the river to have dinner in Lebanon, New Hampshire, one night — but I had nary a conversation with anyone no matter where I was.

And that's a problem. Because the entire solo travel experience hinges on your willingness to step outside of your comfort zone. For those of us who are naturally more introverted, that means striking up conversations with strangers every chance you get and being open to the opportunities those conversations can unlock.

Finding new friends while on the road? There's an app for that

Finding new friends while on the road? There's an app for that

I realize in this overly-digital age of ours that not everyone's communication and social skills are in tip-top shape anymore, but as ironic as it may sound: there's an app for that. Make that multiple apps. And though you may roll your eyeballs in an emphatic manner, Tinder is actually one of those apps that can come in handy — for obvious reasons, I might add. Similarly, Bumble, which comes with three different modes, one for meeting dates, one for meeting friends, and another for networking, is a great app to have on hand in unfamiliar territory. contributor Jaye Hannah put together a list of apps for travelers last October that includes a few other options for people looking to meet others platonically while out on their solo adventures. Some of those include Hey! Vina, an app exclusively for women; Tripr, an app that allows you to meet up with fellow travelers (as opposed to locals); and Meetup, an app that can help you immerse yourself in local activities.

Aside from apps, another way to make the most out of your solo traveling experience is to make connections via an online community like CouchSurfing, a platform that puts travelers in touch with potential hosts for homestay visits. Operating on a gift economy — where hosts are not allowed to charge guests for lodging — the platform also allows you to meet other travelers or to simply meet up with locals if you prefer to find accommodations elsewhere.

Speaking of accommodations... why not stay at a hostel if there's one around? Just like the dorms during your freshman year of college, hostels force you to share a room with a stranger or two, and what better way to make someone's acquaintance than to live in tight quarters with them for a few days?

I don't have much in the way of specific hostel recommendations — unless you're staying in Chicago, Miami, Los Angeles, or New York, that is. In that case, you'll want to check out Freehand Hotels, which offer both hotel- and hostel-type lodging. Just last summer, I stayed at the Freehand in Chicago and ended up going out for a bite to eat with my German "roommate" and a couple of his friends.

When it really comes down to having a positive solo travel experience, though, you really just have to have the right attitude. Even with the apps and the online communities and the various lodging situations, it's on you to make the experience a worthwhile one. When I say my first solo trip was a failure, I have only myself to blame for that. I definitely learned from the experience, and I hope you've taken a little something away from reading this post.

Now go on, get adventurous.