Travelling Solo: What You Want To Know The First Time You Take a Trip Alone

Let your loneliness soften you, not frighten you 

Person seen from the waist down pulling a purple suitcase in an airport

Montreal will always be my first love — the city I chose for my first delve into solo travel. I left my husband and two boys at home in Halifax and ventured away for four full days of freedom. How long can I go? I had pleaded with my husband the month prior to leaving. Can I do five days, six? He winced. How about four? I booked the earliest flight on the first day and the latest on the last. I would milk those four days for all they were worth. 

Compared to Halifax, Montreal was just big enough to feel exciting but close enough to not feel intimidating. Plus, the official language of French made it seem like I had travelled farther than I actually did. 

Travelling alone was everything I hoped it would be and some of what I hoped it wouldn’t. There were moments when I felt deeply lonely, even when squeezed among thousands of people. I dripped with sweat in the thirty-degree heat and suffered an embarrassing set of saddle sores from biking around the city in jean shorts. I got disoriented and took wrong turns and made mistakes — but I never made the same mistake twice. As I walked for blocks and blocks and sceneries changed around me, I learned to depend on the things that didn’t. The mountain that lay big and green to the west, the old city and river to the south, the sun rising bright and hot in the east. 

Every afternoon, I walked to the vegan ice cream shop that sat on a corner two blocks from my Airbnb, rotating between their three daily flavours. Chocolate one day, vanilla and raspberry twist the next, and always on a waffle cone even though it jacked the price up to almost eight dollars. The truth is, I would’ve payed double. It felt like fate that I had chosen a room so close to this sliver of heaven. I drank bubble tea underneath a night sky lit up with fireworks, occasionally getting struck with the soccer ball being kicked around by a group of overtired boys beside me. I sat in parks reading and journalling and watching couples stretched out on picnic blankets drinking chardonnay straight from the bottle. I wandered through the oldest Neo-gothic cathedral in the country, where I sat down on a hard wooden pew and prayed a little, but spent more time in this sacred space scrolling Google’s recommendations for where I could get a smoked meat sandwich for lunch. I crawled under the duvet exhausted each night, yet was only able to sleep for three-hour stretches. 

I missed home and my boys and tried to hide the tears that welled in my eyes during our morning FaceTime calls, but I also felt giddy and free. There is something invigorating about waking up beside your snoring husband one moment and only a few hours later plopping yourself down on the grass in a park a thousand kilometres away. It’s unsettling in the best sort of way. Like this new place has taken the dormant parts of yourself by the shoulders and given them a good shake while yelling, “Time to come out and play!” 

This was just my first adventure in solo travel, but here are a few lessons I picked up along the way: 

Blank space is your friend, not your enemy 

I came to the city with no shortage of recommendations for cafes, bars and restaurants to visit — a list much too long for my four-day stay, but most of my stops depended more on where I was and what I was craving. I had imagined myself spending lots of time on patios sipping sparkling wine — something I don’t have much time for when at home with kids all summer — but instead I was drawn to long walks through the city with regular stops for iced drinks. When I was in my twenties and travelling with friends, I did what I thought I should do. I went to shows and museums and the main shopping districts. But I’m in my late thirties now, and I’ve thrown out a lot of those shoulds. Travelling alone was the perfect invitation to do 

exactly what made me happy. Which, it turns out, was skipping the afternoon trip to the museum and heading back to my room to put on a face mask and lounge around naked in the splendid air conditioning. 

Get familiar with the compass around you 

I can navigate the metro system like a champ. Colour-coded lines, route numbers, and stops written in neat lists are my kind of language. But drop me into a world of new street names and intersections and I feel like someone’s spun me around until I’m dizzy enough to fall over. I quickly discovered how helpful it is to know which cardinal direction I was heading at any given time. It’s something sailors have known for hundreds of years but which we modern travellers rarely need to think twice about. But you’ll be thankful for this little bit of intuition in those moments when your phone dies and you’re left without that glowing GPS in the palm of your hand. Pick a few landmarks that will help you determine which direction is which, and quiz yourself every so often before double-checking on a map. It’s a fun game but also helps you keep your wits about you in new territory. 

Mistakes will happen, that’s a fact 

Even though I wished I left my Airbnb every morning feeling confident in where I was going, and that every decision went smoothly, this was not my experience. I scribbled directions down on pieces of paper and clutched them in my sweaty hand as I biked and yet I still managed to miss a turn now and again. I arrived hot and tired at bike stations that were empty when I needed a bike, and full when I needed to return one. I found myself on roads that were blocked or under construction or void of bike lanes and had to navigate myself out of there. The mistakes I made were my absolute best teachers. Mistakes aren’t the end of the world, even though they feel pretty sucky at the time. And every so often the wrong turn allows you to stumble into something unexpected and beautiful, like lush ivy climbing a brick wall, soaked in afternoon light. 

You have permission to lie 

I was a little nervous about being a woman on my own in a big city. I asked my husband to check in with me at times to make sure I had made it home safely, and texting my sister about my plans for the day helped me feel a little less alone. But this, it turns out, wasn’t quite enough to help me feel secure. Travelling alone can be a great conversation starter, but after an uncomfortable conversation with an overly pushy guy one night, which, afterwards, had me taking the stairs to my room two at a time and bolting the door locked behind me, I decided to keep this fact to myself from then on. My solitude would be my own little secret. Answers I would potentially give when asked: I’m waiting for my husband to arrive; I’m meeting a friend; I’m on a girl’s trip and heading back to the rest of the group. I started using these lines when they felt right. Of course, not everyone’s intentions are bad, and that’s never how I’ve viewed the world — there were plenty of strangers I bumped into that warmed my heart and reminded me of home. But I felt better playing it on the safe side.

Let your loneliness soften you, not frighten you 

When I was planning this trip, one of my fears was that loneliness would prevent me from enjoying myself. I am an introvert through and through, but my daily life is tethered to rich relationships that fuel my need for connection — my husband and our two boys, our families, and a wonderful group of mom friends whom I see regularly. Being alone for four days straight in a city of nearly two million people felt unsettling at times. There were moments I longed for someone to talk to, to just be with, and wondered why on earth I had signed myself up for this solo trip to begin with. But I got through those moments and I tried not to criticize myself for them. Loneliness doesn’t make us weak, it makes us human. We need each other more than I think we realize sometimes. Travelling alone certainly reminded me that the people in my life are as nourishing and as vital to me as the food I eat and the water I drink. 

My wanderlust has been satisfied, my itch to experience solo travel scratched, and my craving for an adventure was fully fed. I came home to the same bright-eyed boys who whine and complain but always make me laugh and the same dirty floors that needed to be scrubbed, and I was deeply, deeply grateful. I had three beautiful faces greet me in the morning whose voices and mess and touch I really did miss. 


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Andrea is a freelance writer in Halifax, NS. Her writing has been featured in Today’s Parent, She Does the City, and Our Children magazine. Before deciding to pursue writing full-time, Andrea received her BEd and worked as an elementary school teacher. When she’s not writing, she can be found wandering through nature, journalling at a coffee shop, or hanging out at home with her husband and their two boys. Usually, she’s eating chocolate. You can connect with Andrea on Instagram