*Post updated on June 18, 2025

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, so I set out by my lonesome for a long drive through Canada that would eventually pour me out into 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 no stranger to solo travel. 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 Factory, Harpoon 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 when those moments present themselves, and being open to the opportunities those conversations can unlock.

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. Contiki.com contributor Jaye Hannah put together a list of apps for travelers that includes several options for people looking to meet others platonically while out on their solo adventures. Some of these 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.

Another way to make the most out of your solo travel 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 by living with them in tight quarters for a few days? I’ve stayed at a hostel only a couple of times — once in Argentina while visiting Iguazú Falls and a second time in Chicago at the Freehand Hotel (which also has standard private rooms) — but I walked away from both with a positive experience.

What solid solo travel experiences really come down to, however, is having the right attitude. No matter the apps you use, the online communities you engage with, or the type of lodging you choose, 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. It’s up to you not to make the same mistake(s).

Now go on, get adventurous.

-LTH

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