8 Things to Think About on Every Solo Trip


This post was contributed by Till Kaeslin

Last fall, I went on my first solo trip to Montreal, Canada… or Montréal if we want to be classy.

Convinced I’d be 10 feet under before my friends would commit to a weekend trip to Canada, I spontaneously booked the bus and hostel I would stay at in the summer on my own.

As a first-generation immigrant born in Switzerland and raised in the US and Hong Kong, China, travel had been a part of my life since before I could even use the web to search for cheap flights. And that was all thanks to my parents, whose itchy feet took us kangaroo spotting in Australia, horseback riding in Mongolia, and on a classic USA cross-country road trip that my parents swear I was present for…even though I was too young to remember anything.

But that was all them, their doing – I was just along for the ride (allegedly). This trip marked the beginning of my own travel career, where I would be the one to shut up and go, call the shots, and carry on the tradition of our globetrotting family all on my own. And I was itching to get the ball rolling on this trip, whether my friends came around to the idea or not.

I had a seat on an overnight bus to Montreal.

A procrastinator by nature (I like to keep things fashionably stressful for myself), I didn’t really think about the trip again until a week before the big day … yikes. With a little red notification in my inbox came a slightly passive aggressive message from Greyhound asking me, “What have you done to prepare for your trip?” Wow… shots fired, Greyhound.

I think that’s when it really started to sink in. I was going on a solo trip. A full-on single ticket, table for one, “no I’m not waiting on anyone else,” solo trip.

As excited as I was, I started to get nervous about the whole situation, questioning everything I had dealt with so nonchalantly in the weeks before: What was I thinking? Why would anyone voluntarily choose to spend a whole weekend alone in Canada? Was it actually so voluntary in the first place? If I couldn’t even convince my friends from home to come on a trip with me, how would I make friends in Montreal?

Spiraling thoughts in action.

Despite all the questions running through my head, I followed through and went on the trip, because my curiosity was greater than the inhibitions that usually held me back. That little red notification in my inbox was staring me right in the eyes and I was too damn stubborn to not follow through on my commitment.

And thank god I followed through because that was one trip I’ll never forget. And despite what all the amazingness of being in a French-Canadian city might make it seem like – mainly talking about the coffee and tall, stylish, 70%-sure-he’s-gay Québécois men – what made the trip so unforgettable wasn’t that it was one long Instagram-worthy weekend.

For all the good moments – meeting interesting people from all over the world, strolling down narrow French inspired streets, and leaving with a new love interest… the city of Montreal – it was also challenging, awkward, and lonely at times. And what’s funny is that, in hindsight, these were the most important parts of my experience. They taught me that it’s ok to be alone, that figuring things out completely on my own could not only be fun but empowering as well.

Needless to say, I’ve been hooked on solo travel ever since – I just came back from another solo trip to New Orleans! So, it only makes sense that I try to pass on the message to those around me.

Here are my tips for those of you planning a trip by yourself in the near future, from one solo traveler to another.

Just Do You

Sleep in or wake up before dawn, party all night or spend the night in, check off all of the ‘top ten things to do’ or none at all – it’s all up to you, because you are by yourself and you get to do whatever you want. Don’t nag yourself to do anything you don’t really feel like doing, just do you, this is your time and no one else’s. Go ahead and order another round of poutine! Don’t sleep on the toppings.  

Once you get in the swing of things and go full shameless, that’s when solo travel really starts to become enjoyable.

Engage Yourself

Laugh with yourself, laugh at yourself, and talk to yourself (I know, sounds crazy, but bear with me here). Get to know YOU in a time when you’re not distracted by other people. Think about it – when else do you have the time to get to know yourself than when you’re by yourself in a place you don’t know, with a couple of complete strangers? Take advantage of that moment and enjoy your own company before you start to get your bearings.

Take a Risk – Make the First Move

If you see people gathered around a dinner table chatting, go and ask them if you can sit and join them. If you see people are getting a group together to go out, go and introduce yourself and go with. Essentially, if you see someone you might want to talk to, don’t just sit there and wait for them to talk to you, make the first move!

When I stumbled into the kitchen to grab dinner on that first night at the hostel, I felt like Lindsey Lohan at the beginning of  “Mean Girls,” but I wasn’t about to take my dinner to the bathroom stall. I forced myself to walk up to the table of about 10 people nearest to me, ask them what was good to eat, and if I could grab a seat. I can’t remember if I ended up deciding on the beef stew or lentil soup, but I do remember that not just 2 hours later I was getting ready to go out and hit the city with about 10 new friends.

As nice as it is for your ego to have people come to you first, making the first move and walking up to that packed table always guarantees you’ll meet the people you want to talk to, and you won’t be left with that awful feeling that you’ve somehow missed out.

Just Say Yes

Same goes for if someone else makes the first move – if someone comes over to talk to you, invites you to eat with them, or invites you out, take them up on it!

It might be an awesome person to hang out with, the future friend of a lifetime, or … you might not get along with them at all! However it turns out, you’ll never know if you don’t say yes (if you feel comfortable, of course)!

Just saying those three simple letters – Y.E.S – in that order, I found myself sitting in a packed Irish bar on Boulevard Saint-Laurent with about 20 or so young travelers, swapping travel stories and trying our best to put together how exactly we, a group of people from all different corners of the world, all ended up together squeezed around two tables we had caused a huge commotion pushing together.

Embrace All of Your Emotions

You’re going to go through a lot of different emotions – that’s a given whether you’re a super emotional person or not. No matter who you are, a routine is part of everyone’s life, and we’re often quick to become reliant on that routine. So when suddenly the script is flipped and you’re all on your own, away from the surroundings and people that are so familiar to you, it can be a tough transition. You’ll have days where you feel crappy, lonely, or homesick and just want to curl up and hide from the world in your hostel top bunk. And that’s ok. You’ll have days where you resurrect after a night out to 5 missed calls from your mom that you may or may not have let roll to voicemail while you were really busy leaning over the bar chatting up the cute Québécois bartender. And that’s ok too – just as long as you let her know you’re still alive and kicking.

Give Yourself Time to Chill Out

When you’re traveling solo, you tend to forget that your brain is on ALL the time, 24/7, and that can get real tiring, real fast and affect the way you think about yourself and your trip. So when you notice you’re starting to burn out, just chill and carve out some you time – which you can easily do, because you’re on your own schedule!

My biggest tip for this would be to do something you would normally do at home to relax – watch an episode of a Netflix series, hang out in a café and treat yourself to an espresso, go for a run – do whatever you need to do to realize that you as a person are location independent; just because you may feel lost in an unfamiliar place doesn’t mean you’ve lost yourself.

Stay Alert

Once you start to settle in, it can be easy to forget that as comfortable and relaxed as you might come to feel, it doesn’t change the fact that you’re in an unfamiliar place with unfamiliar people, both of which don’t owe you anything. Though all of my experiences traveling solo so far have been great (knock on wood), the world is far from perfect and there are people out there that can and will take advantage of you if you make it easy for them. Definitely keep taking the road less traveled, keep putting yourself out there, and treat yourself to a drink or two on a night out – just make sure that you stay in the know.

Remind Yourself that Alone is Not Lonely

If ever you feel awkward, out of place, or lonely (which is guaranteed to happen on any solo trip), remind yourself that despite the fact that your friends and family aren’t there with you, they are still out there, they do still exist, and they’ll be there for you when you come back!

Just because you’re alone at the moment doesn’t mean you’re lonely in life.

Meet Till: I’m a 20-something-year-old, soon to be college graduate (yikes), backpacker, language learner, and “I’ll figure it out when I get there” kind of person – for better or for worse. Right now I’m in Shanghai, China studying Mandarin and making my way around the country. Keep up with my travel moments (and travel fails) here.

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