There’s something magnetic about solo travel in midlife. It whispers possibility — the idea that life can still surprise you. Maybe you’ve built a comfortable routine, a good home, a stable career, and even found peace in your own company. But there’s that itch — the urge to shake things up, to step away from the predictability that’s quietly crept in. Maybe you’ve said to yourself just as I did, “I just don’t want to have no more adventures left in me”. So why the hesitation? Maybe you might be just a little afraid to do a trip alone.
Sometimes, midlife can feel a little like living in your own version of Groundhog Day: same commute, same dinner table, same small circle of celebrations that always seem to belong to someone else.
That’s when travel starts calling your name — not as an escape, but as a reminder that you’re still growing, still curious, still brave enough to do something new.
Travel expands you. It pulls you out of your comfort zone, lets you see how other people live, and gives you a front-row seat to the stunning variety of the world — its foods, cultures, landscapes, and ways of thinking. You start to realize how big life really is.
But when you’re single, that whisper to “just go” can come with a lump in your throat. Because the truth is — wanting to travel and actually doing it are two very different things when you’re on your own.
When the Idea of Going Alone Feels Too Big
If you’ve ever scrolled through travel blogs or Instagram posts and felt a pang of envy, followed by a quick, “but I could never do that alone,” you’re not a weakling. You’re human.
I’ve been there — more than once. In my younger years, I did my fair share of travel: Europe, the Caribbean, parts of South America, and beautiful corners of Canada and the U.S. But back then, I always had a companion — a friend, a partner, family. I was never alone.
I didn’t have to navigate bizarre transit systems in another language solo, or figure out how to be out after 6 pm all by myself, as a woman travelling alone. Let’s face it, who wants to travel all the way to another country, just to sit in your hotel room the minute the sun sets?
It was only when I began travelling without anyone — truly alone — that I discovered just how brave it really is to do it. Because yes, solo travel can be freeing and thrilling, but it can also be intimidating and even lonely at times. There’s no shame in admitting that.
The Three Camps of Midlife Travellers
When I talk to single people over 50 who are thinking about travel, I tend to see three kinds of travellers emerge:
1. The Veteran Soloist
These are the bold ones who have always travelled alone. They’ve mastered the art of wandering. They know the unspoken rules of haggling and hacks, safe ways to enjoy the nightlife, and they’ve got stories about strangers who became lifelong friends. They aren’t necessarily fearless — they’ve just learned to trust themselves deeply.
2. The Suddenly Solo
Then there are those who always travelled with a partner. Maybe they’re divorced, widowed, or simply navigating life on their own now. For them, the idea of travel feels bittersweet — something once shared that now feels uncertain. They stand at the crossroads: do I travel alone, or do I wait for someone to join me? What if I don’t foresee ever having someone to travel with again? Are my travelling days over, and if so, what am I going to do with my vacations for now on?
3. The Semi-Solo Traveller
And finally, some don’t go completely alone — they sign up for group tours, or join a retreat or educational opportunity, where they can enjoy structure, company and safety while still experiencing independence.
No one camp is “better” than the other. Each has its joys and its challenges. But for many of us — especially those in the second and third groups — taking that first step toward solo travel can feel huge.
Courage, Not Comparison
Here’s what I want to say right off the bat: don’t let anyone make you feel small for being nervous. You’ll meet people — especially online — who speak with a tone of smugness about solo travel, as if fear is something to be ashamed of. Ignore them.
I can’t tell you how many people make dismissive comments about how easy it is, and how if I wanted to do it I would, so I must not really want it bad enough. Then, when I ask them for more details, turns out, they rarely travel completely on their own either. It’s all a facade.
Courage isn’t the absence of fear; it’s moving forward despite it. Every time you take a small step — even just researching destinations or booking a short weekend trip — you’re building confidence. And that’s how I’ve always done it. Knowledge is power.
For me, I don’t go anywhere or book anything without learning as much as possible beforehand. It helps reduce any anxiety I might have about my destination, safety, travel hiccups, and potential problems. I feel better equipped, the more I have pre-planned.
The internet is full of experienced solo travellers offering advice, and many are incredibly generous with their knowledge. Just be aware that not every voice out there understands what it’s like to start again at 50 or 60. It’s perfectly okay to take it slow, to ease into it, and to admit that comfort and safety matter to you.
Start Where You Are — Literally
One of the most practical and empowering ways to start is to travel within Canada. We live in an enormous, breathtaking country that offers everything from ocean to prairie to mountain and the Great White North. You can dip your toes into solo travel without dealing with currency exchanges, language barriers, or the potential panic for unanticipated health care issues.
Domestic trips let you practice the logistics of travelling alone — things like navigating transit, making restaurant reservations for one, taking excursions and finding accommodations that suit your comfort level.
You’d be surprised how different things can be, even within your own home country. I can’t tell you how long I stood in front of the signage at the Vancouver Airport train system because it was so different from what I was used to. I couldn’t figure it out, no matter how many times I read the poster on the wall.
And every one was frantically moving past me, in a hurry, knowing where they were going and what to do. It was comical. I wasn’t anxious, but I was confused.
It reminded me of the same scenario I’d been in years ago in Paris, France, trying to figure it all out for their subway (the Metro), all in French which I was never any good at in school. I am trying to correct that now, but it’s still a work in progress.
But back then, I was accompanied by a friend so we were putting two heads together instead of just one and actually having a real big laugh over it.
Thankfully on this day in Vancouver by myself, I had nowhere to be in a hurry because it probably took me about 20 minutes (or felt like it anyway) to make any sense of it. It turns out the further you go in distance the more you have to pay (a new concept for this former Torontonian).
So if you have a wish to travel, do it, even if hesitant. Take small steps. Maybe it’s a weekend in Quebec City, or a few days exploring Vancouver Island, or even a quiet cabin near Algonquin Park. These smaller trips teach you to rely on yourself — and that’s the foundation of every great solo adventure.
My Own First Steps Into Semi-Solo Travel
One of my first trips when I decided to reintroduce travel into my life after 50, started with something structured — an escorted cycling trip by Freewheelin’ Adventures, a family-run Canadian business. We were cycling across Prince Edward Island. They organized everything: the routes, the accommodations, the meals. I was still “travelling by myself” – sort of, but within the safety net of a group.
I was worried cycling all alone could put me at risk should I get lost, get a flat tire, or have a fall.
To save money, I took a gamble and opted for the “find me a roommate” plan. Luckily, it worked out beautifully. An Albertan with an easy laugh and a laid-back personality was my assigned roommate, and we hit it off immediately. We shared friendship, stories, and sore muscles after cycling a leisurely 60-80 km a day.
My roommate actually is married, but had a partner who had no interest in cycling or any kind of travel. So there are even coupled people who make the bold decision to travel alone because they refuse to put their own passions aside just because their partner isn’t into it. Good for them!
These days, I think I would be a bit more reluctant to go for the roommate option but that’s more about me than it is about the concept of room sharing on group tours. It’s weird how protective I’ve gotten over my sleep. C’est le vie.
The group was small — maybe 12-15 people — and we stayed in charming bed-and-breakfasts scattered across PEI. I loved that I could have time to myself for R&R in the afternoons, but also enjoy happy hours, dinner conversations and shared experiences in the evenings.
The staff loaded and unloaded the bikes each day. They would drive us to the next drop off point along the Confederation Trail, then went ahead to meet us at lunch rest locations. They prepared delicious picnic lunches for us to gobble up upon arrival. They were available for quick bike fixes when required.
All we had to do is ride, eat, laugh, and enjoy the scenery. It was the perfect mix of independence and companionship. I had a fantastic week!
For me, that trip changed everything. It reminded me that I could still explore — safely, joyfully, and on my own terms.
Travel With a Theme to Make Fast Friends
If you’re still a little reluctant to join strangers, consider a themed trip or retreat. Themed travel brings people together with at least one thing in common — whether that’s cycling (like my trip), painting, yoga, history, studying a new language or even cooking.
One summer, I joined a four-day yoga and paddleboarding retreat in Algonquin Park on Kawawaymog Lake in Ontario. The days were filled with early morning and afternoon paddles, healthy meals, yoga sessions both on and off the SUPs and evening bonfires. I never did master the headstand on the paddleboard, but it sure was fun trying and watching all the others make a big splash as well.
The chef, passionate about farm-to-table cooking, gave mini lessons before each meal. I met fascinating people — many of whom were also navigating midlife changes and rediscovering themselves. Shout out to Northern Edge Algonquin. It was perfect!
That trip reminded me that connection doesn’t require companionship. Sometimes, it’s found in shared experiences with strangers who are on their own parallel journeys. And maybe one day I’ll make a life long friend on one of these adventures.
When Solo Travel Isn’t for You (And That’s Okay)
Some people love cruises. I’ve done many — all of them with family or friends and my last one done alone. And I’ll be honest: the solo one wasn’t for me. I missed the shared experience of standing on the deck, pointing out whales or laughing at bad karaoke.
Without a companion, I didn’t enjoy drinks in the bar, didn’t go dancing, or play any of the group games. I just couldn’t find a way to fit in, despite my best efforts, friendliest smiles and willingness to follow all the advice from cruise forums telling solos how to have a successful cruise.
I tried everything, alas, my efforts were big fat bombs. Maybe they’ll work for you, so don’t trust my only solo cruiser experience. Maybe it was just the combination of people on that particular cruise. It may have been poor timing, too close to coming out of the pandemic, and people just weren’t inclined to want to mix with anyone other than their group to avoid getting ill. Who knows.
Don’t get me wrong. It was still a wonderful week because I am fascinated by geography and wildlife. I was mesmerized by the beauty of the ocean and the mountains. I love the Alaskan coast. However, for me, I’ve decided that in the future, taking a cruise by myself just isn’t likely in the cards.
That’s okay. Solo travel isn’t a one-size-fits-all experience. What matters is finding what feels right for you.
Maybe you love group tours because they take the planning pressure off.
It could be you prefer train travel or a river cruise, where you can meet people naturally along the way.
Perhaps you love sitting quietly in a café in a city where no one knows your name and spending lovely afternoons walking through museums.
The point is — your version of solo travel is just as valid as anyone else’s.
The Budget Reality
Of course, we can’t talk about solo travel without acknowledging the cost. Travelling alone often means paying the dreaded “single supplement” — the extra charge for occupying a room meant for two. Often, we are required to pay for the full cost of two, even though we are one. It’s exorbitant!
When no one’s splitting the bill, the costs of car rentals, accommodations, and beach rentals adds up quickly.
It’s one of the biggest barriers for solo travellers, especially now with inflation and rising living costs. I’ve had to cancel or scale back my own travel plans because of this reality.
But here’s the good news: the industry is slowly catching up. Some tour companies — like Just You — a UK based co. with Canadian representatives, specialize in solo travel and don’t charge extra for single occupancy.
G Adventures, a Canadian company, has a strong reputation for small group travel where solos are welcome.
And EF Go Ahead Tours markets directly to travellers over 50 who want structure and company without feeling out of place.
As always, do your own research on these companies before you go. I have not had the pleasure of using them myself, although I know someone who has used G Adventures and had a great trip.
There’s also Road Scholar. Learning as you travel. A friend loved their Costa Rica trip. I cannot personally endorse any of these companies, but it’s a start when you are beginning your own research.
Even cruise lines are starting to introduce solo cabins — a small but important shift that acknowledges we’re a growing demographic. Though for now, there are often only a few cabins per ship, very small interior rooms usually. But it’s a start, right?
To Book or Not to Book Through an Agent
I’ll be honest — I’ve had mixed experiences with travel agents. There are excellent ones out there, but there are also some who don’t seem to understand the needs of solo travellers or the details of the destinations they’re selling. I’ve heard that it’s when things go wrong on your trip that a travel agent can really smooth the waters, so it’s worth considering.
If you choose to use one, get recommendations from people you trust. A good agent can save you a ton of stress — especially with complicated itineraries or international travel. But if you’re comfortable online, you can absolutely book your own flights, hotels, and excursions.
I have used 3rd party travel sites like Booking.com and Expedia in the past with absolutely no issues so for me it was a success. Again, check them out, follow up on recent reviews and make your own educated opinion. Rules, policies and service can change over time.
Recently, I have been booking directly with the airlines and hotels. But for you, maybe you figure it’s worth the gamble, and that’s ok too. The key is to double-check cancellation policies and insurance coverage — especially as a solo traveller.
Accommodation Choices — Comfort Over Criticism
You’ll find a lot of debate online about where solo travellers should stay: hotels, hostels, Airbnbs, or house sits. My advice? Stay where you feel safe.
For my first few solo trips, I only booked major hotel chains in the downtown core. Yes, they were more expensive. And yes, other travellers might roll their eyes at that. But that sense of security — being in a well-known, staffed hotel close to the attractions — was worth every penny to me.
Maybe one day I’ll be ready for the charm of a little guesthouse partway out of town, or on a backstreet. But for now, I go where I can rest easy. And that’s okay. Solo travel should never be about proving yourself to others. It’s about knowing yourself.
Growing Braver, Not Fearless
Over time, something shifts. What once felt terrifying starts to feel doable. You start making small decisions with ease: which restaurant to try, how to get from the airport to your hotel, when to chat with strangers.
You may even start to like being your own travel companion — doing what you want, when you want, without compromise. That freedom can be addictive.
Still, not every day will be perfect. There might be a lonely evening, a missed connection, or a lost cell phone that leaves you frazzled. But those moments don’t define your trip — they’re part of the story you’ll one day tell with a grin.
Final Thoughts
Travelling solo in midlife isn’t about running away from anything. It’s about stepping toward something — toward courage, toward curiosity, toward the reminder that life doesn’t stop giving you new experiences just because you’re no longer part of a couple. Embrace the changes and the possibility with a life pivot that opens a whole new path.
So if you’re hesitating, if you’ve been sitting with that mix of wanting but not wanting to go — know that you’re not alone in feeling that way. Every solo traveller started right where you are: uncertain, excited, a little afraid.
Start small. Take that first trip. Book the retreat. Go see what’s beyond the edge of your familiar.
Because whether you go across the country or across your own region — the most important journey is the one where you remember who you are when no one else is beside you.
Check out my YouTube video on how living solo builds resiliency, by clicking this link:
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