Where should I go? How long should I stay? Should I get a visa, go solo, or bring a friend? These are the questions I’ve been asking myself (and maybe you are too). In this post, I dive into how to balance your gut instincts with practical choices, from budget and visas to life goals and what you leave behind. Plus, a peek into my own planning process as I figure out my next adventure at 25.
One of the biggest (and most intimidating) parts of travel isn’t picking flights or packing your suitcase, it’s deciding where to go, and how long to stay.
It sounds easy until you actually start planning, then suddenly the questions pile up:
- Do I go somewhere I’ve always dreamed of, or somewhere more affordable?
- Should it be a quick trip or a long adventure?
- Solo, or with someone else?
- Is it worth what I’d leave behind?
I don’t have all the answers (spoiler: no one does), but here’s how I’ve tried to figure it out, and maybe it’ll help you too.
Follow your gut (and your heart)
Honestly, this is where it always starts for me.
Sometimes it’s a single photo, a video, or even hearing someone talk about a place — and suddenly, you can’t stop thinking about it. That quiet, stubborn feeling that says “go.”
And trust me: your gut knows more than your spreadsheet does.
Some of my best trips started because something just felt right, not because it made perfect sense on paper.
Cost vs. dreams
The hard truth: you might have to balance what you want with what’s realistic.
Dreaming of six months in Paris? It’s possible, but only if you can make the budget work.
So I ask myself:
- Is this a place I’d love to experience deeply, slowly?
- Or would a shorter trip still feel special?
Sometimes it means trading a big luxury trip for a longer stay with simpler comforts, and sometimes it means saving up to really do it your way.
Neither answer is wrong; it just depends on what matters most to you.
Long-term vs. short-term
I’ve done both, and they really do feel like different worlds.
Long-term (6+ months):
You discover favourite cafés, spot locals you recognize, learn shortcuts, celebrate holidays abroad, even find a little routine. You live there, not just visit.
Short-term (a week, a month):
It’s exciting and fresh; you squeeze in sights, meals, and memories. It’s more intense, but sometimes exactly what you need.
Ask yourself what you want from the trip: depth, variety, or a mix? And remember, you can always go back.
Solo or not?
Travelling solo scared the life out of me at first, but it taught me so much about who I am when no one else is around.
You choose what you do, learn to trust yourself, and realize how capable you are.
Travelling with a friend or partner, though, is just as wonderful in a different way. Someone to share laughs, split snacks, take photos, hype you up, and navigate challenges together.
Your choice might depend on your personality, destination, or even just the season of life you’re in. Neither is “better” they’re just different stories.
Visa vs. no visa
Some places let Canadians stay months without a visa. Others offer working holiday visas, which, trust me, are truly once-in-a-lifetime. I learned this the hard way: once it expires, you can’t apply again!
Visas can feel like paperwork headaches, but they unlock deeper experiences: working, renting an apartment, staying longer than a tourist ever could.
If you’re under 30 (sometimes 35), look into them, it’s a window that doesn’t stay open forever.
The money question
No one loves budgeting, but it’s freeing to know your limits.
Ask yourself:
- Do you want hostels, markets, and street food?
- Or boutique hotels and fancy dinners?
- Will you work along the way?
It’s not just “how much do I have,” but “how much do I want to spend on this experience?”
What you leave behind
The part we don’t always talk about: family, friends, pets, partners, birthdays, jobs.
Travel doesn’t exist in a vacuum; something always gets paused or missed.
For me, I weigh:
- How long am I willing to be away?
- Will I regret missing something at home?
- Is the trade-off worth it right now?
Sometimes the answer is yes. Sometimes it isn’t. But being honest with yourself matters.
Where you are in life
I think a lot about age and timing.
Where do you see yourself in five years? Will this trip fit into that plan, or change it?
Some travels feel best before bigger commitments; others fit beautifully at any stage.
There’s no deadline to see the world, but sometimes, your life stage helps guide when and where to go.
The “how long” question
It’s not always about visas or money; sometimes it’s emotional:
- Do I want to feel settled somewhere?
- Do I just want a burst of adventure?
- Do I want to keep moving or stay in one place?
There’s no rulebook. I’ve loved quick city breaks and months-long stays, each gave me something different.
The final thought
When people ask me how to choose where to go and for how long, the truth is: there isn’t a formula.
Start with your heart, check in with your reality, and ask yourself:
- Where lights you up?
- What can you afford; in money, time, and what you’d leave behind?
- And what feels right for right now?
And remember: there’s no perfect choice, no “best” way.
The important part is that you go at all.
Because whether it’s a weekend, a month, or a year… you’ll come home different.
And that’s always worth it.
My personal experience
Right now, I’m in that planning stage again.
I’m always super excited for my next adventure, but there’s always that little battle in my head:
Where do I go? How long do I go for? Should I get a visa? Who should I go with? What am I potentially leaving behind? Should I follow my gut or my heart?
And now, being 25 (oof), I’m starting to think about a five-year plan for myself and what I want my future to look like. If I don’t travel now, then when will I? But if I keep travelling now, what will my next five years look like?
I don’t think anyone truly knows the “right” answer. I sure don’t. But I do know that in the end, I’ll come to the answer that’s right for me.
And maybe that’s the point.
Halfway to Somewhere 