The 3 Questions I Now Ask Before Choosing a Destination
Originally broadcast 9th February 2026, via email
Choosing where to go on holiday is harder now than it has ever been.
We’ve got endless travel blogs listing the best places. Social media showing us viral viewpoints and “hidden gems” that definitely aren’t hidden. And AI doing… whatever AI does.
And whilst all of it is technically there to help, it can quickly become overwhelming.
Trust me, we’ve been there. In fact, it’s where we found ourselves recently.
When planning our Thailand trip, there was never a question about whether we would go to Chiang Mai. I had heard so many good things. Social media told me to go. Travel blogs told me to go. Every backpacker we met told us it was their favourite place.
So of course we should go, right?
Well… maybe not.
This is absolutely no hate to Chiang Mai. It’s a lovely destination and I completely understand why people love it. But since being there, we realised something important:
It wasn’t right for us.
And that feeling? It’s more common than you think.
You hype a place up in your mind because everyone tells you it’s a must-see. You build it into something magical. Then you arrive and feel… disappointed. Deflated. Almost mis-sold.
I’m sure you’ve experienced it too.
So now, before I even book the trip, I ask myself three questions. They’ve completely changed how we choose destinations, and they’ve saved us from a lot of misplaced expectations.
1. What Do I Actually Want From This Trip?
This has to come first.
Not “where looks good on Instagram?”
Not “where is trending?”
Not “where does everyone say I have to go?”
But: what do I personally want to feel and experience on this trip?
Am I craving relaxation?
If I’m burnt out, overwhelmed, or tired, I don’t need a chaotic city packed with museums and must-see sights. I need slow mornings, sea breeze, nature, and space.
Am I craving adventure?
If I want hiking, surfing, adrenaline, exploration, I need mountains, coastlines, trails, and accessibility to them.
Am I craving culture and sightseeing?
Then yes, give me temples, architecture, history, markets, and walking tours.
The mistake we made with Chiang Mai wasn’t that it wasn’t good. It was that we didn’t properly define what we wanted before we arrived.
At that point in our trip, I was craving nature. Greenery. Big landscapes. Space to breathe.
Chiang Mai is a city. A beautiful one, but still a city.
And when you’re not aligned with what you need, even a “perfect” destination can feel slightly off.
Clarity removes disappointment. If you know what you want, you can choose somewhere that actually delivers it.
2. Does This Destination Have the Infrastructure I Crave?
This is the underrated one.
You can want relaxation or adventure all you like — but does the place support the way you like to travel?
For me, that often means:
- Cute coffee shops where I can sit and write
- Good vegetarian food options
- Walkable streets
- Green spaces
- A nice “vibe”
For you, it might mean:
- Reliable WiFi
- Affordable co-working spaces
- Beach bars
- Luxury hotels
- Easy English communication
- Great public transport
These things sound small, but they shape your daily experience massively.
If you love slow mornings in aesthetic cafés, but the destination is more street-food-stall heavy with limited seating, that might subtly frustrate you.
If you hate driving, but the destination requires a car to access everything, that might drain you.
If you’re vegetarian or vegan and food is central to your travel experience, that matters.
It’s not about judging the place. It’s about being honest about your preferences.
We often pretend we’re more adaptable than we are. But travel is meant to be enjoyed. There’s no medal for forcing yourself into situations that don’t suit you.
3. Are The Main Things I Want To Do Easily Reachable?
This is the practical one.
You might want waterfalls, viewpoints, beaches, or mountain temples. But how easy are they to actually access?
- Is there good public transport?
- Can you hire a car within your budget?
- Are roads safe and manageable?
- Can you walk between key attractions?
- Are day trips realistic without exhausting yourself?
Sometimes destinations look incredible on a map, but the logistics make them harder than expected.
For example, if all the nature you want to see is an hour’s drive away on winding mountain roads, and you’re not confident driving them, that totally changes the experience.
If public transport is limited and taxis are expensive, your budget might stretch further than planned.
Ease of access impacts energy levels. And energy levels impact enjoyment.
When everything feels simple and reachable, travel feels light. When everything feels like a mission, it can quickly feel heavy.
Why These 3 Questions Matter
The internet will always tell you where to go.
There will always be a “best city,” a “hidden gem,” a “must-see destination.”
But the best place for someone else might not be the best place for you. At least not right now.
That’s the key.
Destinations aren’t good or bad in isolation. They’re right or wrong for you in a specific season of life.
And that season changes.
The three questions I now ask are simple:
- What do I want from this trip?
- Does this place support the way I like to travel?
- Are the experiences I want easily accessible?
If I can confidently answer yes to all three, I book it.
If I hesitate, I dig deeper.
It’s not about avoiding popular places. It’s about choosing intentionally instead of reactively.
And since we’ve started doing this, travel has felt lighter. More aligned. More exciting.
Less “we should be loving this” and more “this feels exactly right.”
And honestly? That shift alone has changed everything.
